The current binomial Sonochemistry-Analytical Chemistry

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The current binomial Sonochemistry-Analytical Chemistry Carlos Cairós a, Javier González-Sálamo a, Javier Hernández-Borges a,b,∗ a

Departamento de Química, Unidad Departamental de Química Analítica, Facultad de Ciencias, Universidad de La Laguna (ULL). Avda. Astrofísico Francisco Sánchez, s/no . 38206 San Cristóbal de La Laguna, España b Instituto Universitario de Enfermedades Tropicales y Salud Pública, Universidad de La Laguna (ULL), Avda. Astrofísico Francisco Sánchez, s/no . 38206 San Cristóbal de La Laguna, España

a r t i c l e

i n f o

Article history: Received 7 June 2019 Revised 17 August 2019 Accepted 2 September 2019 Available online xxx Keywords: Ultrasound Sonochemistry Analytical chemistry Green chemistry Review

a b s t r a c t Although around 90 years have passed since Richards and Loomis developed the first experiments in sonochemistry, ultrasound is still awakening interest in the scientific community, in particular in the Analytical Chemistry field, as a result of the high number of benefits achieved, which are also in accordance with Green Analytical Chemistry principles. In the last years, and among the different reported applications, an important number of works have arisen devoted to the synthesis of new materials (specially nanomaterials), to the development of sonoelectroanalytical sensors or to new spectroscopic approaches, among others. Efforts are also being made to try to understand the real mechanism of such applications. This review article is aimed at providing a general overview of the different applications of ultrasound in Analytical Chemistry, also briefly highlighting its fundamentals and traditional applications, with a special emphasis on the most recent and challenging works that are still in the horizon of its near future. © 2019 Elsevier B.V. All rights reserved.

1. Introduction Sonochemistry is the application of ultrasound (US) to chemical reactions and processes [1], being US the region of the sound spectrum between 16 kHz and 10 GHz -though this upper limit is flexible between authors [2]. The physical and chemical effects that US can create in different media, have also allowed their wide use in other disciplines like medicine or physics as well as in many industrial applications. The first experiments in sonochemistry were developed in the 1920s by Richards and Loomis, who measured the effects of the application of high US frequency on several solutions, solids and pure liquids [3] finding that US accelerates a broad range of transformations. To achieve such experiments, the previous works of the brothers Pierre and Jacques Curie in 1880, when the piezo-electric effect in certain crystals was demonstrated, were the real breakthrough [4]. Despite the diversity of the effects of US shown in that first work, it was not until the 80s when the advances in US technology allowed the development of more specific, accurate and efficient applications, when low-cost and consistent generators of high-intensity US were developed [2]. The chemical disciplines that ∗ Corresponding author at: Departamento de Química, Unidad Departamental de Química Analítica, Facultad de Ciencias, Universidad de La Laguna (ULL). Avda. Astrofísico Francisco Sánchez, s/no . 38206 San Cristóbal de La Laguna, España. E-mail address: [email protected] (J. Hernández-Borges).

first experienced the benefits of US cavitation were Organic Chemistry and Electrochemistry [5–7]. In the first of them to assist organic synthesis (only very few works were published until 1980) [8]. On the contrary, the application of US in Analytical Chemistry took place sometime later, basically to assist sample pre-treatment procedures and automatic analytical systems [7] though electroanalytical techniques also pioneered the use of US cavitation [9]. Until the beginning of the XXI century, most applications of US in research were based on an empirical approach, black box style, based on a trial-error test and on the analysis of the results without really knowing what the real effects of US on each specific application were. With the subsequent advances in high-speed videography or photography, among others, an increase in the location, generation and control of cavitation bubbles was achieved, together with a simultaneous advance in nanotechnology and nanoobservation. These advances positioned US at a new level, with an outstanding number of possible applications, which can clearly be seen from the subsequent increase of the number of peer-reviewed publications in the topic (see Fig. 1). Knowing the mechanism of what is really taking place when cavitation bubbles are present, though not an easy task, is the best way of increasing the utility and application of the use of US in different fields, especially in Analytical Chemistry. Although the term “sonochemistry” might seem clear or appropriate for many scientists, there exists an ambiguity in the literature, up to the point that some authors even avoid using it and recommend calling it US cavitation chemistry [10], which is proba-

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Fig. 1. Evolution of the number of publications since 1980 in which the term “ultrasound” is included.

bly more intuitive and precise. The fact is that a general definition of sonochemistry involves all chemical processes affected by cavitation bubbles [1] which can have either physical/mechanical or chemical effects, as it will be later shown. The first of them include strong flow or shear forces, shockwaves, stirring, microstreaming, high temperatures and pressures [11], while the second comprises sonolysis and recombination of the molecules inside the bubbles as well as their exposure to extreme conditions of temperature and pressure and phase changes [12]. Other authors define sonochemistry, or what they call ‘real’ sonochemistry, as the phenomena related with radical generation inside cavitation bubbles. During this text, we will use the global definition, grouping all chemical processes or reactions promoted or enhanced by cavitation bubbles through any of their possible effects. Regarding specific Analytical Chemistry applications, US facilitates almost every stage of the analytical process, from preliminary steps (i.e. cleaning, degassing or atomization) to sample preparation procedures (digestion, emulsification, leaching, derivatization, extraction, etc.) or even analyte detection. At this point it should be highlighted that professors Luque de Castro and CapeloMartínez, among others [5,12–14], have reviewed in a good number of occasions different ways in which US can be successfully applied in the analytical laboratory. However, the conditions at which such applications have been developed are very disparate (also in the particular case of the applied frequencies) and, in many cases, it has not even been fully understood what the real effect of US in such procedures is. In the last years, great efforts have been developed to try to establish the mechanisms implicated in the different applications in which US is involved. Besides, an important growth in the number of works devoted to the US assisted synthesis of nanomaterials (which are one of the current research trends in the Analytical Chemistry field) has taken place, as well as in all kind of sample preparation. That is why the aim of this review article is to provide a general overview of the most recent and prominent applications of US in this field, in particular, of those challenging studies that go beyond the “classical” assistance of extractions (black box style) which could be its future directions and opportunities some of which try to provide an explanation of the US mechanisms involved.

2. Back to basics The fundamentals and principles of US have been extensively reviewed in different occasions by experts in the field [11,17,18]; however, we would like to briefly summarize relevant information to better understand its application in Analytical Chemistry. 2.1. Effects of ultrasound in liquids Chemical and most physical effects of US in liquids are not rising from the direct interaction between waves and molecular species. Instead, these effects are coming from acoustic cavitation. US waves passing through a liquid generate, if the conditions are adequate, cavitation bubbles [19]. It should be remarked that a high viscosity and a high surface tension of the solvent precludes their formation and, therefore, the temperature of the liquid has also an important effect in cavitation. Such bubbles follow a specific cycle of compression and expansion (related with the frequency and amplitude of the wave and liquid conditions) until their final collapse (see Figure 1S of the Supplementary Material). The liquid in the bulk solution can enter the gas bubbles in the compression phase by rectified diffusion and can exit the bubble in the expansion phase. Inside the bubbles, as well as in the gasbulk liquid interface, conditions are extreme, especially at the final compression bubble radius, where estimated temperatures and pressures are extremely high [20,21]. These conditions favor chemical reactions, phase changes and physical effects in the substances present in the bulk liquid, inside and nearby the bubbles in micro volumes of the liquid randomly distributed. In this sense, collapsing bubbles can be considered as microreactors. The range of the frequencies most used in sonochemistry goes from 20 to 10 0 0 kHz, although the range of application is wider and can be extended until 30 0 0 kHz [22] since above 10 0 0 kHz, cavitation bubbles are difficult to generate and/or to observe as a result of their extremely small size. Each bubble collapse potentially produces local pressures around 20 0 0 atm and temperatures around 50 0 0 K in aqueous solutions [23], although higher temperatures have been estimated in other solvents [21] as well as pressure shockwaves, liquid jetting and microstreaming [24], which also have a specific interest in cer-

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tain applications. However, the bubbles are so small that heat is quickly dissipated. Additionally, this process can lead to the formation of plasma and radicals by the lysis of molecules, water included. In fact, in the presence of cavitation, water breaks in radicals, which is a phenomenon very studied, resulting in a highly reactive system (see Figure 2S of the Supplementary Material). In the same manner, other volatile substances decompose in different products inside the bubble [25]. Other mechanisms, as the injection of microdroplets of the liquid in the vapor phase by bubble deformation of microjets, have been confirmed to be responsible for the reactivity of non-volatile species [26]. The bubble size and the intensity of the collapse depend strongly on the applied frequency. In fact, at frequencies between 16 and 100 kHz (which is the range most frequently used in Analytical Chemistry applications), bubbles are relatively large (from 10 0 to 50 0 μm in radius), bubble collapse is intense and physical effects are violent, including jetting, shear and high temperatures [24]. Some authors name this region as the power US region [11]. On the contrary, the intermediate US region, ranging from 100 to 10 0 0 kHz, is the most sonochemically active region [27], which maximizes radical formation, since the number of bubbles as well as their stability increase. Physical effects are moderate in this region. Finally, above 10 0 0 kHz, physical effects become relatively soft due to the small bubble sizes, but radical production is still possible though in a much lower proportion. This region is important for applications where very gentle physical effects are required and is often named as the diagnosis or megasonics region [17]. It should also be highlighted that it can be made a distinction between primary sonochemistry, if the reaction happens in the bubble interior, and secondary sonochemistry if the reaction takes place in the bulk liquid, as a result of interactions with radicals or species produced inside the bubbles [28]. An alternative classification divides sonochemical reactions into homogenous, liquid-liquid reactions that occur through the chemical effects of sonochemistry, by free radical production, or heterogeneous sonochemistry [29], in two phases reactions (liquid-liquid or solid-liquid) that are enhanced or promoted by the mechanical effects of US, such as surface cleaning, particle size reduction, and enhanced mass transfer [30]. It should be remarked that to achieve cavitation collapse, a gas should be dissolved in the liquid; however, since US has a degassing effect such gas should be continuously bubbled into the liquid. In this sense, monoatomic gases such as He, Ar and Ne are preferable to diatomic (i.e. N2 , O2 or even air) or polyatomic gases (i.e. CO2 ), which are not recommended. The addition of surfactants also facilitates cavitation [31]. 2.2. Ultrasound devices Apart from the previously mentioned effects of the application of US, it is also important to consider the type of ultrasonic device to be used. In this sense, as a general methodology, sonication can be applied in Analytical Chemistry using two approaches: directly to the sample or indirectly through the walls of the sample container. In the first case, it is important to consider that direct exposition may provide metal contamination, erosion and heat transmission while when indirect exposition is applied, loses of energy trough the walls of the container and changes in cavitation active zones might be the principal difficulties (in general, a loss of ultrasonic efficiency) [2]. In both cases, if US is applied in open vessels, etc. volatile compounds may be lost. Researchers must select the most suitable approach for each specific application. A general configuration of any sonoreactor might be represented as shown in Figure 3S of the Supplementary Material, requiring a transducer to convert mechanical energy into US. Traditionally, sonochemistry has been performed in available commer-

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cial equipment that has not been designed for this purpose: i.e. ultrasonic baths designed for cleaning, or ultrasonic probes, mostly used in biological laboratories to sterilize the medium, control bacteria population, etc. It should be remarked that in non-chemistry applications, there exist other types of equipment. More and more present in the market today, custom sonoreactors will hopefully consolidate a position in commercial catalogues soon, as an instrument designed to perform and control chemical reactions. Concerning ultrasonic baths, they are currently present in almost all Analytical Chemistry laboratories (see Figure 4S of the Supplementary Material), since there exists a wide variety of models and are also highly affordable. General instruments specifications include a fixed working frequency and amplitude. They work at very high amplitudes, possibly/frequently overpassing the optimum power to perform sonochemistry and yielding complications, because of the very violent collapses of the bubbles, such as strong erosion or high heat transmission to the liquid. Modern ultrasonic baths are more versatile and allow the use of different frequencies (i.e. dual or multi-frequency), the control of temperature, time and amplitude, the application of continuous or discontinuous frequencies, etc. They are made of stainless-steel tanks with transducers fixed to their base. The range of frequency might oscillate between 25–20 0 0 kHz. On the contrary, ultrasonic probes (sonotrodes or ultrasonic horns) are device tips that conduct the sound into the liquid (see Figure 5S of the Supplementary Material) that can be made of stainless-steel or titanium. In this case, since more concentrated energy is applied (normally directly into the solution), metal contamination, erosion and heat transmission to the system may occur. However, it allows to focus US energy in small volumes of the liquid and to have less energy loses. Tips are easily to replace and relatively inexpensive. Ideally, a sonoreactor should be specifically designed for the required application, taking into account the volumetric needs and adjusting geometrical and US factors and external gas supply to the characteristics of the container and of the solution to treat. In the literature, a good number of different designs can be found [32]. If such a customized design is not possible (which frequently occurs), a flexible instrument that allows the selection of different frequencies and wave amplitudes is highly desirable. A complete characterization of the reactor might accomplish the location of the cavitation active zone and the optimization of US power and frequency for the specific application [33]. Another important factors to be considered are the type and amount of gas injected in the system [34,35] that might affect bubble population, and the cooling of the system, important for processes that requires constant temperatures. In this sense, Gogate et al. [36,37] and Bussmaker et al. [38] have recently published an interesting review on the topic that might be consulted at the time of designing a sonoreactor and choosing the right experimental conditions. 2.3. The secret relies on the bubbles 2.3.1. Physical or mechanical effects of ultrasound As mentioned before, the implosion and collapse of cavitation bubbles, can drastically change the properties of solids and liquids surrounding the bubbles. In this sense, there exist three main physical effects that should be remarked: bubble jets, microstreaming/microflows and shockwaves. 2.3.1.1. Ultrasound cavitation bubble jets. A cavitation bubble near a solid boundary does not implode spherically but in a toroidal collapse movement that ends with a violent liquid jet passing through the center of the bubble (see Figure 6S of the Supplementary Material) [39]. Violent jetting of thousands of bubbles produces the

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Fig. 2. General scheme of the rectified diffusion process in an oscillating cavitation bubble.

cleaning and sterilizing effects of US over surfaces [24,40,41]. Liquid jets might promote the dissolution or the extraction of solid phase substances into the liquid phase by the fragmentation or erosion of solid boundaries. Violent jets might also be implied in avoiding passivation processes at electrode tips [42] and in the enhancement of mass transfer observed in electrochemical processes, although US streaming must play a principal role on that surgical movement fast and precise propulsion of the liquid. 2.3.1.2. Ultrasound streaming. Acoustic streaming can be settled without cavitation bubbles, as it is not a direct effect of cavitation bubbles but of heat and convection effects near the transducer’s surface. It is, however, a simultaneous effect that is always present if cavitation bubbles appear [2]. Bubble collapse, jets or other bubble interactions can also produce microflows or microstreaming (see Figure 7S of the Supplementary Material [43]) that might be useful for specific applications. 2.3.1.3. Shockwaves. The collapse of cavitation bubbles also generates powerful shockwaves that are often associated with erosion or breakage issues, but that can also favor several chemical processes by particle fragmentation, surface modification or electrode depassivation, among others [30]. 2.3.2. Chemical effects of ultrasound cavitation The process behind the chemical effects of US cavitation bubbles is the so-called rectified diffusion. Bulk liquid enters and exits the gas phase, during the collapse and expansion phases of a cavitation bubble (see Fig. 2). Chemical species can enter the bubble gas phase, in gas or liquid phase [25,44], while they are exposed to extreme conditions of pressure and temperature, including the formation of plasma, and exit the bubble in a different chemical form. As a result, cavitation bubbles behave as micro-reactors inside a liquid. Gas and liquid phases are exposed, in occasions simultaneously, to extraordinary fast changes in temperature and pressure. A micro-volume of the bulk liquid can exist at a given moment as bulk liquid under normal conditions but, for example, a microsecond after it can subsist under gas phase as a mixture of radicals and, 10 microseconds after, it can even form a complete new substance, again at normal conditions of temperature and pressure. Cooling ratios as high as 1010 K/s and plasma formation at the end of the compression cycle confers US cavitation unique characteristics to promote or enhance chemical reactions [45]. 2.3.2.1. Radical formation and their release into bulk liquid. The well-studied radical breaking of water under sonication, most known as sonolysis, turns the universal solvent into the reactant,

offering new routes for traditional reactions [27]. As an example, it can be cited the reduction of HClAu to gold nanoparticles, where the radicals coming from water act as the reducing agent [46]. Even more, a small amount of an organic alcohol like, for example, propanol or butanol, can break immediately into radicals, in contact with cavitation bubbles, thanks to their high volatility, which has also shown an extraordinary impact in the kinetics of reactions, making them faster by a factor of 10–50 times [47]. The power to turn molecules into radicals in a short time increase the general reactivity of any solution and has found several applications in many fields of chemistry [2]. A “bright” example is the sonochemiluminescence of luminol, which is activated by the radicals produced during sonication generating a visible map of cavitation activity that becomes especially useful in the design of sonochemical reactors [48,49]. Luminol chemiluminescence has become one of the most used qualitative measurements (and also quantitative if suitable calibration is developed) of radical production by US. Another example widely used is the oxidation of iodide [50] in aqueous solutions or the fluorescence of terephthalic acid, among others [19,51–53]. In general, when a homogeneous process is developed, those reactions that are sensitive to the sonochemical effect proceed with radical formation or radial-ion intermediates. For heterogeneous processes, the mechanism is much more complex, since ionic intermediates can also be involved [1]. 2.3.2.2. Plasma chemistry. Sonoluminescence (SL) is the emission of radiation produced by the molecules inside a cavitation bubble. It is, indeed, an extraordinary phenomenon, whose origin is not well understood yet, but that has been controlled and deeply studied by researchers around the world in the past two decades [54]. In this case, light appears at the end of the compression cycle of a bubble, whose intensity depends on the content of the bubble. Spectroscopy of emitted light is possibly the most powerful tool to study conditions inside a cavitation bubble. Researchers currently know that at the minimum radii phase of compression cycle, where SL occurs, the bubble interior is in a plasma state [55,56]. This fact is extending the sonochemistry experimental space into plasma chemistry within very small volumes of sample and very short times (in the order of microseconds). Another consequence of SL spectroscopy is that non-volatile species emit during SL, which implies that non-volatile species in the liquid are also submitted to the extreme conditions inside the bubble. A model where liquid droplets of liquids get in contact with the gas phase by non-spherical collapse or by jetting of the bubbles has been suggested and proven [20,57]. Small droplets of the bulk liquid in contact with a plasma state, or extreme conditions in a very small volume of gas, opens the opportunities for reactions of

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non-volatile species, in the field of nano- and microchemistry, and would be behind the mechanism of extreme sonochemical reactions as graphite transformation into diamond [58]. It is important to notice that many chemical processes currently use US though the nature of the benefit remains unclear. In many cases, they might benefit from a single effect or both of them simultaneously. The two effects are present whenever US is applied and can be modulated with US experimental parameters, adjusting frequency and acoustic power, after a proper characterization of the sonoreactor, though it is rarely possible to totally neglect one over the other. A good analysis of the variables involved in sonochemistry can be found in the review of Bussemaker et al. [38]. 3. Well-established applications of ultrasound in Analytical Chemistry As previously commented, professors Luque de Castro and Capelo-Martínez, among others [7,13–16], have reviewed several times the application of US in Analytical Chemistry. In fact, professor Luque de Castro wrote in 2007, together with professor Priego Capote, the first book dealing with the specific use of this type of energy in this field, which provided an excellent and detailed description of each specific application of US [59]. From those works, and also from a detailed revision of the literature, it is clear that US cavitation has been widely used in Analytical Chemistry in a good number of sample preparation steps [13,59,60], including preliminary steps such as cleaning, degassing, or atomization, which are the principal reasons why US equipment is commonly found in many chemical laboratories. Besides, US cavitation has been systematically applied in different chemical processes such as dissolution, digestion, leaching and slurry of solid samples, filtration, aggregation and crystallization of solids as well as in the assistance of different extraction procedures [13]. Mechanical effects of US cavitation related with their capacity to mix, erode surfaces or heat have been associated with all the benefits obtained by using US, since they have been confirmed as the dominant effect in cleaning or degassing phenomena [2,61]. However, as previously indicated, chemical effects of US are very frequently neglected, without the necessary empirical confirmation. The key point when applying US cavitation lies in understanding the processes, the substances involved and the effects that cavitation bubbles might have on them, from both points of view: mechanicals effects and chemical effects coming from radical production. Accuracy at the time of fixing and reporting experimental conditions, and monitoring physical and chemical changes before and after US cavitation is applied, might help gaining knowledge about the real effects of US in the systems, and to solve some of the ambiguities and contradictions frequently found in literature [14]. 3.1. Extraction and ultrasound cavitation There currently exists an extremely high number of publications on the combination of US cavitation and extraction (ultrasound-assisted extraction -UAE-), most of them based either in liquid-liquid extraction (LLE) and solid-liquid extraction (SLE) [62–64], including their miniaturized versions [65,66]. The number of publications is still growing year by year consolidating the application of US in this field, especially those related with miniaturized techniques. The extraction method will define the US mode that will be more appropriate, depending on the interactions between the bubbles and the liquids or solids. In SLE, conditions provided by cavitation bubbles (which mainly collapse at solid surfaces) make the interaction between the solid and the liquid more efficient. In fact,

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UAE is more frequently applied to solid matrices than liquid ones. In general, US provides an effective contact between the solid matrix and the extraction solvent, reduces the extraction time and the volume of organic solvent required. Several extractions can also be simultaneously and reproducibly developed, using low-cost equipment. Swamy and Narayana [67] proposed a model to explain the mechanisms behind the UAE of solids. Without US, the solvent penetrates through the sample and analytes are diffused to the outer region. When US is present, cavitation bubbles collapses will occur preferably at solid surfaces, which generate a rapid adiabatic compression of gases and vapours within the bubbles or cavities with a high local increase of temperature and pressure. Such situation increases the solubility of the analytes and their transfer to the solvent (which is also helped by the presence of US) as well as the introduction of the solvent into the solid matrix [68]. In general, the velocity of analyte leaching is increased. Close to a solid boundary, cavity collapse is rather asymmetric and produces highspeed jets of liquid, this also may break solid particles. Liquid jets driving into the surface at speeds close to 400 km/h have been observed [24]. The main problem in this case might be compound degradation by the effect of the radical formation during cavitation or the mechanical effects of the bubbles [30], and the possible decomposition of the solvent, arising only, in this case, from the chemical effects of sonochemistry. Hence, good knowledge of US parameters is extremely important, including a good experimental factor design and control to modulate, if possible, chemical effects versus physical effects. US is also frequently applied to help during the extraction or desorption process of sorbent-based extraction techniques. The application of US in the presence of an extraction sorbent will imply the risk that cavitation bubbles affect the integrity of the sorbent. Despite this fact, it has been used with success in, for example, magnetic and non-magnetic dispersive solid-phase extraction (dSPE) [69,70]. Table 1 shows some recent examples of such applications. Concerning the specific case of solid-phase microextraction (SPME) or stir-bar sorptive microextraction (SBSE), US has hardly been used, probably because they are more prone to affect the structure of the sorbent and the sorbent retention onto the support used. In LLE, cavitation bubbles collapses help to form emulsions between two immiscible liquids. However, such emulsions can be frequently very stable with long phase separation times. That is why US has not been so frequently used in LLE as they have been in SLE, though the use of miniaturized techniques is also changing such tendency. US capacity to produce emulsions, their uses and their mechanism, have been deeply investigated, shortly after sonochemistry was discovered [84] until today [85,86]. As it was confirmed in the last revision of the mechanism [86], it is a process mostly dominated by the mechanical effects of the bubbles, although radical chemistry could also play an important role in function of the composition of the mixture and the experimental parameters involved. In this sense, as a principal drawback, it is necessary to guard the possible degeneration or destruction of the solvent or reactant by controlling these experimental factors or using it favourably. As it also happens in SLE, the amount of extraction solvent as well as the extraction time is reduced by applying US. Furthermore, the main drawback of its application in LLE is also compound degradation, which has been observed in certain cases [87–89]. The formation of emulsions by US has found a good application area in dispersive liquid-liquid microextraction (DLLME) which avoids the use of a dispersion solvent and provides an effective formation of emulsions which increases the contact between the donor and the acceptor phase (in some cases the amount of organic solvents is also reduced) [90,91]. Concerning DLLME it has also been used with non-conventional solvents like deep eutectic

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Extraction technique

Sorbent/solvent and extraction conditions

Desorption conditions

Analytes

Matrix

Hybrid cobalt ferrite natural organic matter (20 mg), agitation 150 rpm or 5 min US (- kHz, - W)

10 mL ethyl acetate and US for 2.5 min

5 PAHs

Water (10 mL)

UA-SPE

Magnetic iron oxide particles (40 mg) and Aliquat 336 ionic liquid mixed hemimicelles (2 mL 2% in EtOH), US (21 kHz, 60 W) 10 min 2 mL buffer pH 3.0, 15 mL sample, 300 μL THF, 250 μL of DES (tetrabutylammonium chloride: decanoic acid (TBACl-DA, 1:3 M ratio)) and 3 min US (- kHz, - W)

0.5 mL ACN (6 min without stirring)

2 nitrophenols and 2 chlorophenols

Tap and river water (50 mL pH 8)

–

Quercetin

40.0 μL of CCl4 , 0.8 mL ACN, 2 min US (- kHz, - W), centrifugation 5 min UA-CPE: DDTC 0.03% v/v, TX-114 0.06% v/v, 55 °C 20 min US (40 kHz, 200 W), centrifugation 5 min, dilution with EtOH to 3 mL UA DLLME: DDTC 0.05% v/v, CCl4 , 10 min US (40 kHz, 200 W), centrifugation 5 min, dilution with EtOH to 3 mL 10 mL of the powder solution, 650 μL of DES (choline chloride:phenol 1:4), 550 μL THF, 30 min US (40 kHz, 250 W), centrifugation 25 min a dilution with 500 μL mobile phase

–

4 PBBs

–

Copper

Tomato, onion and grape (1 g, dried at 70 °C, extracted with 10 mL EtOH 3 h, water until 15 mL) Tap and sewage water (5 mL) Lake, river, tap and bottled water and cola drink (40 mL at pH 11.0)

–

5 pesticides

UA-dSPE

5 mL of sample, 13 mg of carbon supported ZnS (nanoparticles), 6.5 min vortex, 6.5 min US (- kHz, - W), decantation

1.0 mL of acetone

Chlordiazepoxide and diazepam

UA-DLLME-SFO

3.0 mL of Milli-Q water, 1% w/v NaCl, 24 μL of 1-undecanol, 4.8 min US (- kHz, - W) at 30 °C, centrifugation 3 min, cooling in an ice bath and separated

–

7 PCBs and 11 OCPs

DES-UA-DLLME

UA-DLLME UA-CPE and UA DLLME

DES-UA-DLLME

Traditional Chinese medicines (1 g of powder sample extracted with 100 mL of boiling water for 2 h) Urine and plasma

Recovery

Comments

References

94.0–99.4% (RSDs <1.0%)

LODs: 0.010–0.020 μg/L. UA m-SPE provided the best results LODs: 0.005 to 0.041 μg/L. 30, 45 and 60 W were tested LOD: 18.8 μg/L

[71]

[72]

70.0–119.0% (RSDs <10.0%)

[69]

UV (370 nm)

91.0–110.0% (RSD <5.0%)

HPLC-UV (226 nm) UV–Vis (434 nm)

75.8–105.0% (RSDs <6.5%) 90.2–109.0% (RSDs -%)

LODs: 0.11–0.12 μg/L

[73]

LODs: 0.7 μg/L for UA-CPE, 0.8 μg/L for UA DLLME

[74]

HPLC-DAD (220 nm)

81.0–92.1% (RSDs <4.7%)

LODs: 0.02–0.2 mg/L

[75]

HPLC-UV (220 nm)

88.4–97.2% (RSDs <6.2%)

[76]

GC-μECD

88.5–108.4% (RSDs <10.0%)

LODs: 1.2–1.5 μg/L. Extraction was developed into an end cap glass pipette tip. LODs: 1.06–3.84 ng/g

[77]

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Fish liver (1.0 g extracted with 5 mL acetone 20 min; overnight at −20 °C to remove fats and evaporation to dryness)

HPLC-FD (λexc/ λem : 266/384 and 290/430) HPLC-UV (280 and 370 nm)

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UA m-SPE and m-dSPE

Analytical technique

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Table 1 Some recent examples of the application of US in different sorbent and solvent-based extraction procedures.

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Extraction technique

Sorbent/solvent and extraction conditions

Analytes

DES-UA-DLLME

0.03 g of DES (Trioctylmethylammonium chloride:decanoicacid 1:3), 80 mg NaCl, 5 min US (40 kHz, 150 W), centrifugation 4 min, dilution of the droplet with 80 μL of MeOH 78 μL [C6 MIM]PF6 , 81 μL [C4 MIM-SH]Br (dispersant), 7 min US (), 13.5 min cooling and 3 min centrifugation

–

3 UV filters

–

3 bisphenols

m-dSPE

100 mL of sample pH 8.0, 30% w/v NaCl, 10 mg Fe3 O4 @SiO2 @MIM-PF6 , 1 min US (40 kHz, 50 W)

500 μL MeOH, 6 min US (40 kHz, 50 W)

6 UV filters, 4 parabens and bisphenol A

UA-MR-IL-DLLME

15 mL of sample pH 7.0, 100 μL 0.4% APDC (0.4 mg), 120 μL IL [Hmim][PF6 ], 100 mg of Fe3 O4 , 6 min US (40 kHz, 100 W)

300 mL of 2 mol/L HNO3 , 2 min US (40 kHz, 100 W)

Cd(II), Pb(II)

Tap, river and well water

UA-DLLME

1 mL of sample, 30 μL C2 H2 Cl4, 200 μL tetrahydrofuran, 1 min US (- kHz, - W), centrifugation, evaporation and reconstitution in 5 μL 50% (v/v) MeOH and 5 μM S-(-)-ropranolol in water. 10 mL of sample, 10% w/v NaCl, pH 7.0, 200 μL thymol:camphor 1:1, 500 μL of ACN, 14 min US (35 kHz, W), 5 min centrifugation

–

Warfarin enantiomers and two metabolites

–

21 PAHs

UA-IL-DLLME

DES-UA-DLLME

Matrix

Analytical technique

Recovery

Comments

Swimming pool water (8 mL)

HPLC-UV (254 and 290 nm)

82.1–106.5% (RSDs<7.2%)

LODs: 0.15–0.30 μg/L

[78]

Milk (3 mL, deproteination with 200 μL 20% HOAc, centrifugation) and juices (3 mL, centrifugation) River, sea and swimming pool water (100 mL)

HPLC-FD (λexc : 233; λem : 303 nm)

91.6–107.9%

LODs: 0.13–0.82 μg/L

[79]

UHPLC-PDA (254 nm); HPLC-QqQMS/MS GFAAS

>87.0% (RSDs 8.3%)

[80]

Urine and serum (pH adjustment, deproteination and centrifugation)

CE-UV (306 nm)

91.9–109.9% (RSDs< 8.0%)

LODs: 0.16–1.21 μg/L. Magnetic nanoparticles coated with an ionic liquid. LODs: 0.1 μg/L and 0.15 μg/L, respectively. Cd-APDC and Pb-APDC complexes were extracted by the Fe3 O4 nanoparticles. The IL first extracted the analytes (DLLME) which were later extracted by the nanoparticles LODs: 0.34–0.38 nM. Sample stacking was used to increase CE sensitivity.

Effluents

GC-Q-MS

73.5–126.2% (RSDs <6.1%)

LODs: 3.9–9.8 ng/L

[83]

References

97.1–101.5% (RSDs<3.4%)

[81]

[82]

7

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[C4 MIM-SH]Br: 1-(4-thiol)-butyl-3-methylimidazolium bromide; [C6 MIM]PF6 : 1-hexyl-3-methylimidazolium hexafluorophosphate; μECD: micro-electron capture detector; ACN: acetonitrile; APDC: ammonium pyrrolidine dithiocarbamate; CE: capillary electrophoresis; CPE: cloud point extraction; DA: decanoic acid; DAD: diode array detector; DDTC: diethyldithiocarbamate; DLLME: dispersive liquid-liquid extraction; dSPE: dispersive solid-phase extraction; EtOH: ethanol; FD: fluorescence detector; GC: gas chromatography; GFAAS: graphite furnace atomic absorption spectrometry; HOAc: acetic acid; HPLC: high-performance liquid chromatography; IL: ionic liquid; m-dSPE: magnetic dispersive solid-phase extraction; LOD: limit of detection; MeOH: methanol; MIM-PF6 : 3-methylimidazolium hexafluorophosphate; MR: magnetic retrieval; MS: mass spectrometry; MS/MS: tandem mass spectrometry; OCP: organochlorine pesticide; PAH: polycyclic aromatic hydrocarbons; PBB: polybrominated biphenyl; PCB: polychlorinated biphenyl; PDA: photodiode array detector; Q: quadrupole; QqQ: triple quadrupole; RSD: relative standard deviation; SFO: solidification of floating organic droplet; SPE: solid-phase extraction; TBACl: tetrabutylammonium chloride; THF: tetrahydrofuran; TX: Triton X-114; UA: ultrasound-assisted; UHPLC: ultra high-performance liquid chromatography; UV: ultraviolet; Vis: visible.

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Desorption conditions

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Table 1 (continued)

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solvents (DES), ionic liquids (ILs) or even magnetic ionic liquids [92] (see Table 1). Very frequently, the only variable that is optimized during UAE is the ultrasonication time. It is very rare to optimize crucial variables like extraction frequency and power, the pulse mode operation (if ultrasonic probes are used) or the position of the sample vessel in the bath or the distance to the probe which determines the energy received. Temperature, which increases during US application, could also be controlled, especially during long irradiation times. 3.2. Promotion or enhancement of chemical reactions It is currently well-known that sonochemistry can enhance many types of reactions in many forms [1,19], offering often shorter times and new greener routes, saving energy and reactants. In this sense, there are many types of reactions that have made use of US to achieve such goals: derivatization, hydrolysis, organic synthesis, redox and degradation reactions [16,29,93–95]. In general, homogenous non catalysed reactions are less influenced by US than heterogenous ones [96]. In a good number of occasions such reactions have also been part of an analytical method, as it is exposed in Luque de Castro’s work, “The role of US in analytical derivatizations” [95], in which they reviewed the uses of US in analytical derivatization, describing its possibilities in most classical derivatization reactions as depolymerisation reactions, redox reactions, esterification reactions, alkylation reactions, addition reactions, ethylation of organometallic compounds or complex formation [95,97]. US-assisted derivatization has been proposed as one of the green methods that might be promoted in the future, under the guidelines of Green Chemistry, to perform derivatization [98]. Delgado-Povedano and Luque de Castro published a review, in 2014, pointing out the possibility that using derivatization and extraction in a simultaneous step of the analytical process towards continuous systems more according with Green Chemistry principles [99]. Since then, several works have continued the trend [98–103]. As an example, the recent work published by Zhang et al. [103], where they perform the simultaneous determination of lactic acid and pyruvic acid in tissue and cell culture media by gas chromatography after in-situ derivatization and US-assisted emulsification microextraction, using the effects of cavitation bubbles to enhance derivatization and also the extraction in only one step. Processes that involve toxic, biologic, volatile or, in general, difficult-to-manage analytes, benefit from the one-step, one-pot characteristics of sonochemistry [95,103,104]. It is also well-known that US can promote compound degradation by lysis of the molecules, via radical or ionic intermediate formation. This ability has been extensively applied in water treatment [89,94,105] in which US has demonstrated to be highly effective. In catalysis degradation, US has also been extensively applied to enhance the efficient of common catalysers, resulting in a new term: sonocatalysis [106]. Common sonocatalysts have been TiO2 [107], CdSe [108], CdS [109] and ZnO [110], among others. Some recent examples include the degradation of acid red 51 and acid blue 74, reactive yellow 39 and anthraquinone [111–113]. Concerning Organic Chemistry, there is a vast amount of work, reflected in a high number of scientific publications and reviews [93,114–117], some recent examples are the first works of US induced solvent-free condensation reactions, forming a Schiff base 1 and a 1,3-indandione 2 from the reaction between o-vanillin and 1,2-phenylenediamine by ultrasonic irradiation [118] or the synthesis of simple organic biomolecules in aqueous solutions containing dissolved prebiotic gases [119]. Added to the mentioned advantages, US cavitation offers the possibilities to perform reactions in intricate or aggressive environ-

ments. Sonochemical reactions in micro-channels or micro-reactors are currently being investigated as a faster and greener methodology compared to conventional methods [120]. 3.3. Electroanalytical chemistry The applications of sonochemistry in the field of electrochemistry are very well established as it is suggested by the high number of publications in scientific journals, and more and more, by its integration in industrial processes. A thorough review about the topic is the book edited by Pollet [121]. Sono-electrodeposition, particularly, electroless deposition in nonmetallic samples, is the most extended application outside Analytical Chemistry [122] while sonoelectroanalytical chemistry developed in a remarkable way among other applications of US in Analytical Chemistry. US provides better detection limits and robustness in adverse environments, as it helps in the main critical factors that limits electroanalytical applications, passivation of the electrode and slow mass transfer [123]. Compton and Banks found several applications where electrochemical analysis detection limits were amplified by the use of US cavitation, and they summarized it in various reviews [124–126]. Mass transfer enhancement is the suggested mechanism behind the increase in sensitivity detected when US cavitation is present, although the real mechanism is still under study [121]. Bubble collapsing and acoustic streaming in the nearby of an electrode produce liquid flows that, consequently, induce an increase in current on the electrode, and helps to clean the electrode surface, allowing electrochemical reactions to happen under extreme environments, where experimental conditions did not allow to perform electrochemistry before [124]. Some examples are the determination of heavy metals in alcoholic beverages or the determination of Cd in the presence of surfactants by sono-anodic stripping voltammetry (sono-ASV) [127]. Applications of sono-cathodic stripping voltammetry (sono-CSV) as the determination of lead in river bed sediment [123] or of manganese in instant tea [123], the detection of nitrite in egg [123] or vanillin in vanilla extract by biphasic sonoelectroanalysis, are evidences of the capacity of US to make electrochemistry a suitable technique to work in complicated environments. An example of how Analytical Chemistry has also helped to learn about sonochemistry stands with the arrival of microelectrodes, that meant a significant advance in electrochemistry as they came to solve some of the classical limitations of the technique related with low detection limits and passivation [44]. Chronoamperometry under these conditions becomes a suitable tool to measure mass transfer disturbances in very short times and very low intensities and it has been successfully used as analytical tool to better understand cavitation phenomena [41,44,128] relating mass transfer enhancement with small changes in current, in the order of microamperes. 4. Prominent applications Apart from the previously and well-established applications of US in Analytical Chemistry, in the last years the following have also emerged and are increasingly being used in the field. In some cases, such applications are not directly related with the analytical process but with the obtaining of suitable extraction sorbents or stationary phases which is also a trend in this field. 4.1. Synthesis of nanoparticles/nanomaterials The explosion of nanotechnology and nanoparticles synthesis has had an enormous impact in an extremely high number of analytical methods. In the last years, scientists of all disciplines

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have used sonochemistry as a new route to synthetize all kind of nanoparticles and nanostructures and this is clearly a new research horizon of US cavitation [129–132]. Among the advantages of the use of sonochemistry in nanostructures synthesis, the following stands out compared with other synthesis methods [131]: • • • • • • •

•

Use of low (room temperature) bulk temperature. Shorter reaction times. Low (atmospheric pressure) reactor pressures. New routes that lead to new materials. More reproducible synthesis. Facile selectivity of sizes, geometries and doped materials. Greener synthesis, reduction or absence of solvents, catalyser, initiators, etc. Increased active area, more complicated and tuneable porous structures.

US cavitation chemical abilities can be used to gather molecules into greatly ordered structures (which is not always achieved) and when this happens the process is frequently called by some authors sonocrystallization [133,134]. Although the mechanism of crystallization under the effect of US is still ambiguous, there are evidences that can shorten induction time [133]. Cavitation bubbles provides enough energy to overcome the stabilizing barrier, resulting in the formation of many crystalline nuclei, as many as active bubbles, that facilitates further crystallization [132]. Two principal mechanisms can be distinguished in sonochemical synthesis. In primary sonochemistry, on the left of Fig. 2 [129], volatile molecules are injected in bubble gas phase, by bubble motion, and exposed to extreme conditions inside the bubble where the reaction occurs. Secondary sonochemistry refers to the case when species generated during cavitation (inside the bubble) later affect other species in the bulk solution. Because of the facile, low-cost and green routes that sonochemistry provides, many researchers have sonochemically synthesized a wide range of different nanoparticles with a direct application in Analytical Chemistry and with even a wider range of application. In the next lines we will highlight some of the principal nanostructures achieved and their main applications, focusing in materials with possible uses in analytical science, specifically in sorbentbased extraction techniques and in sensors and biosensors used for analysis. 4.1.1. Synthesis of extraction sorbents 4.1.1.1. Synthesis of metal and metal oxide nanoparticles. Several types of single metal nanoparticles, metal oxide nanoparticles [135–137], as metal bromide and sulfate nanoparticles, among others, as well as many types of magnetic nanoparticles of different geometries and shapes [138,139] have been synthetized through sonochemical routes. Enhanced properties, lower reaction times, smaller sizes are, once more, advantages of the nanostructures obtained by sonochemistry. Special mention deserves in-situ, facile synthesis of bimetallic nanoparticles [140]. As examples, Liang et al. obtained Au–Ag, Au–Pd nanoparticles with different shapes, silver nanoplates and ring-like gold nanocrystals [139]. Salvati et al. developed the synthesis of Dy2 (CO3 )3 [141], and they conclude that the use of US irradiation in the synthesis of dysprosium hydroxide nanotubes by Dy(OAC)3 and N2 H4 has a notable effect on the morphology of the particles produced. Chang and collaborators [142] investigated the US-assisted preparation of magnetic magnesium–aluminum layered double hydroxides and their application for removing fluoride. Sonochemistry drastically shortened the time being required for preparation of the crystalline composite. They found that US decreased the size of the composite particles and increased the specific surface area, being favourable to the improvement of the adsorption capacity.

9

Dutta and co-workers synthetized MnWO4 and MnMoO4 and

α -Ag2 WO4 nanorods and applied them to Cu(II) and dyes removal [143,144]. In their first work, spherical MnWO4 (surface area of ca. 127.0 ± 0.4 m2 /g) and MnMoO4 (surface area of ca. 112.0 ± 0.5 m2 /g) nanoparticles were prepared and used to effectively remove rhodamine B and methylene blue from water at pH 3–5 (ion exchange mechanism) in few minutes (depending on the sorbent amount which was around 10 mg). The adsorbed dyes could be desorbed from the nanosorbent surface by annealing at 225 °C which could be reused. Cu(II) was also removed from water samples but required a higher extraction time (300 min for MnMoO4 and 15 min for MnWO4 ). Regarding the second work, α Ag2 WO4 nanorods with an average diameter of 15 to 25 nm and a surface area of ca. 115.0 ± 0.2 m2 /g were obtained and used for rhodamine B, methylene blue, and malachite green removal from water. One hundred percent of all three dyes in spiked water at 20 mg/L were removed in less than 10 min (also under an ion exchange mechanism) though pH had to be adjusted to 5 for rhodamine B and malachite green and to 3 for methylene blue. The sorbent exhibited a higher affinity for rhodamine B. Such nanorods were not only promising for dyes removal, but also shown a bactericidal effect. In both works, specific US conditions were used to synthesize each material. The procedure was simple and quick, though it would have been ideal to compare their results with nanoparticles synthesized by other procedures. 4.1.1.2. Metal organic frameworks (MOFs). MOFs have emerged in the last 30 years as revolutionary materials with applications in societally and industrially relevant domains such as storage of fuels (hydrogen and methane) [145], capture of gases (e.g. greenhouse gases) [146], extraction sorbents [147–149] or stationary phases [150]. Regarding their synthesis, to date different approaches have been developed for this purpose, including conventional electric heating (solvothermal or hydrothermal methods), and microwave, electrochemical, room temperature and surfactant-assisted synthesis [151]. The low reaction times in sonochemical synthesis of nanoparticles was motivation enough to synthetize these porous materials, as an alternative to the conventional and often very time-consuming methods, in particular, solvothermal synthesis. Additionally, sonochemical methods implies a greener route by saving energy and amounts of reactants. As an example of the sonochemical synthesis of MOFs, Jung et al. obtained Zn4 O(BTB)2 (BTB = 4,4´ ,4´´ -benzene-1,3,5-triyltribenzoate), also called MOF-177 by sonochemical, microwave and solvothermal methods [152]. The size of the particles synthetized by US and microwaves was smaller than the sizes obtained by the solvothermal method. BET (Brunauer–Emmett–Teller) surface was similar in solvothermal and sonochemical methods, and superior to microwaves. In CO2 adsorption tests, sonochemical synthesis yielded better results. Ahn and co-workers obtained with similar routes, Mg-MOF-74, MOF-5, ZIF-8 and IRMOF-3 membranes [153– 156]. The time needed was not superior to 1 h in all cases, and particles obtained were high quality crystals with high N2 and CO2 adsorption capacity. Masoomi and coworkers prepared, recently, a Cd(II) based MOF (TMU-7) and Zn(II) nano plate MOFs in a short reaction time [157,158]. They tested their adsorption capacity of dyes and concluded that ultrasonic synthesized particles offer an increment in BET surface area. Another example is the work of Abazari who prepared a MOF of [Zn(ATA)(BPD)]∞ with nano-plate shape and 3D channel framework and optimized US conditions to obtain enhanced BET surface area and porosity [159]. Besides, they tested 2,4-dichlorophenol adsorption which was higher in materials obtained by US, possibly by the porosity improvement. Abbasi et al. were also able to synthesize CuBTC MOFs by US and mechanosynthesis methods [160]. Sonochemical synthesized parti-

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cles had a slighter inferior adsorption capacity than synthetized by other methods, as it showed N2 adsorption test. Uptake and release of crystal violet and methylene blue, on the contrary, was remarkable superior. An interesting application was developed by Abbasi et al. in which azine-functionalized zinc cation MOF nanostructures upon silk fibres were synthesized under US irradiation [161] and studied for the adsorption of morphine. Thin films of two threedimensional porous Zn(II)-MOF (TMU-4 and TMU-5 -which were crystalline-) were deposited on surfaces of natural silk fiber (with -COOH surface functionalization) layer-by-layer under US irradiation. Initially, silk fibres were immersed in an alkaline solution in order to deprotonate the acidic groups. The growth of TMU4@silk and TMU-5@silk fibres was achieved by sequential dipping in alternating beakers containing aqueous Zn(NO3 )2 and a dimethylformamide solution of 4,4 -oxybisbenzoic acid and the ligand, which was 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene, for the first of them, and 2,5 -bis(4-pyridyl)-3,4-diaza-2,4-hexadiene, for the second. Both beakers were immersed in an US bath working at 350 W. The first layer was obtained by immersing the silk-COO− surface into the solution of Zn(II) and then in solution of donor ligands. When the negative fiber was immersed in an aqueous solution of Zn(NO3 )2 , Zn(II) ions are attracted to the fiber surface. The dipping step in the solution of the donor ligands allowed the formation of the MOF and initiated the formation of a new one. When the reaction was carried out without US assistance, it was found that the particle size was higher and more irreproducible. Among both MOFs, TMU-5 can retain morphine better than TMU-4. These are only some examples in which the synthesis of MOFs has been highly improved, including their performance, for analyte removal studies (to the best of our knowledge, they have only been applied with this purpose). However, further research may soon appear concerning their application is specific sorbent-based extraction techniques. At this point it should also be highlighted that in many Analytical Chemistry manuscripts in which MOFs obtained following “classical” synthetic procedures are used as sorbents, they are later “magnetized” by putting them in contact with already synthesized magnetic nanoparticles under US for a certain period of time [162– 164]. This has nothing to do with their synthesis, but it is a very frequent practise to develop magnetic extraction procedures with these materials. 4.1.1.3. Polymer nanocomposites. US has also emerged as a powerful tool to produce fast and efficiently free radical polymerization free of initiators allowing to enhance and control the fabrication of polymeric composites, coated magnetic and non-magnetic particles and many other nanostructures. While shear forces generate emulsion droplets, radicals generated within cavitation bubbles react with monomer molecules to generate monomer radicals that diffuse into monomer droplets to initiate the polymerisation process [165,166]. With the use of US, it is possible to perform polymerization in the presence of inorganic nanoparticles that can result in the formation of finely dispersed/encapsulated polymer nanocomposites [167]. Furthermore, it is possible to achieve the polymerization in the absence of initiator or surfactant (or for lesser amounts of surfactant -if it is required-) that result into a pure polymer nanocomposite, what makes US-assisted polymerization a green process. Encapsulation of inorganic nanoparticles into polymer matrices has great applications in many fields of chemistry, physics, medicine, or material science. Emulsion polymerization [168], suspension polymerization [168] and precipitation polymerization [168] are the methods most used to synthetize polymers. Traditionally, no US assistance has been developed in those procedures.

However, using US it is possible to reduce the size of the polymer nanocomposite with a finer dispersion of the inorganic nanoparticles in the polymer matrix compared with conventional preparation methods [169]. It also enhances various properties such as mechanical, anticorrosive, thermal, rheological and gas sensing properties of the hybrid polymer nanocomposite, principally because it increases the loading of inorganic nanoparticles in the polymer [167,170,171]. Price et al. [165] reported in 1992 the first polymerization initiated by US while Biggs and Grieser [172] elucidated in 1995 its synthetic mechanism taking into account the radicals liberated by cavitation bubbles. Since then, several works have made use of US to assist the synthesis of polymers. Xia et al. [173], for example, also studied the mechanism of polymerization by US in the polymerization of n–butyl acrylate and prepared in-situ polymer encapsulated carbon nanotubes [174]. Park et al. [175] performed the simultaneous dispersion and in-situ polymerization of single wall carbon nanotubes while Morel et al. [176] obtained Fe3 O4 @SiO2 core-shell with remarkable magnetic properties suitable for separation and extraction techniques. Teo and coworkers proposed a facile route to synthesize magnetic latex nanoparticles using Fe3 O4 and poly(benzyl methacrylate) latex [167]. The obtained particles kept a strong magnetic response, evidencing abilities for their used as sorbents in extraction procedures. Shirsath et al. [177,178] made a nanocomposite hydrogel combination with an adaptable structure which shows its promising characteristic as sorbent for organic pollutant recovery. Other applications can be found in [179– 183]. As a very recent example, it could be highlighted the work of Lamaoui et al. [179], who studied the effect of various porogen solvents (i.e. dimethylsulfoxide, dimethylformamide, ethanol, acetonitrile and acetone) on the synthesis of a magnetic molecularly imprinted polymer (MMIP) since, as previously indicated, the solvent may affect the reactivity and, therefore, the product yield [184]. The MMIP sorbent was applied for the determination of sulfamethoxazole in spiked tap and mineral water showing satisfactory recoveries (83.0–95.4% with RSD values lower than 2.5%) and moderate reusability (up to 8 times). This work was based on a previous one of Frizzo et al. [185] in which the sonochemical heating profile for 25 solvents (including ionic liquid doped solvents) was determined at amplitudes of 20, 25, and 30%. Magnetic nanoparticles (Fe3 O4 ) were first synthesized by a coprecipitation method and dispersed in Milli-Q water. Oleic acid (primary surfactant) was then added and the mixture was sonicated (5 min). Afterwards, sodium dodecyl sulfate (secondary surfactant) was added and the mixture was sonicated again (10 min). In this way a stable ferrofluid solution was obtained. Then, a pre-polymerization solution containing sulfamethoxazole (template molecule), the solvent and methacrylic acid (functional monomer) was prepared. Self-assembly between the analyte and the functional monomer took place after 1 h. Afterwards, ethylene glycol methacrylate (crosslinker) was added to the mixture, the two solutions were mixed, and the polymerization was developed by adding ammonium persulphate as initiator and by introducing in the solution an US probe (see Fig. 3). The synthesized MMIPs was washed with a mixture of methanol:acetic acid to remove the template. After testing different amplitudes and synthesis times, it could be observed that acetonitrile and acetone did not allow a significant obtention of the polymer, since they slowed down the heating and, therefore, the polymerization rate. In general, MMIPs were successfully synthesized using dimethylsulfoxide, dimethylformamide and ethanol using low amplitude values (20–30%) and -in less than 10 min, leading to high binding capacities. After characterization it was observed that all particles had a spherical shape, with estimated sizes of m-NPs, MMIP- dimethylsulfoxide, MMIP- dimethylformamide and MMIP-ethanol were 18 ± 4,

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Fig. 3. Synthesis of magnetic molecularly imprinted polymers based on ultrasound probe (MAA: methacrylic acid, OA: oleic acid, SDS: sodium dodecyl sulfate, EGDMA: ethylene glycol dimethacrylate, APS: ammonium persulfate, RT: room temperature). Reprinted from [179] with permission from Elsevier.

78 ± 23, 111 ± 21 and 215 ± 44 nm, respectively. It was concluded that the choice of the solvent was very important since the synthesis process is strongly related to the dissipated ultrasonic power of the solvent. A MMIP was also synthesized under US and characterized by Sánchez-González et al. for cocaine and three metabolites (enzoylecgonine, cocaethylene and ecgonine methyl ester) retention against major components (mainly sodium and chloride) and other therapeutic drugs/drugs of abuse in urine [181]. Recovery values were in the range 79–106% (RSDs ≤ 11%). It was found that US speeded up the MIP synthesis around the Fe3 O4 particles, allowing its accomplishment in 4 h, and a more homogeneous size distribution of the composite MMIP particles.

4.1.2. Spectroscopy Spectroscopy has been the principal analytical technique in the study of cavitation bubble internal conditions. Experiments are based in the more eye-catching effect of ultrasonic cavitation: SL [186]. As mentioned before, a bubble in the final compression ratio (when conditions of temperature and pressure are higher) can emit light, depending on the content of the gas phase and the bulk liquid properties. The spectroscopic study of SL has yield important information about the processes that happened inside the cavitation bubbles [23,57]. Emission of noble gases [20], volatile and non-volatile species [20] have been recorder in the UV–Vis region, providing important information about the extreme conditions of temperature and pressure inside the bubbles, helping to understand the mechanisms of sonochemistry [20]. Surface-enhanced Raman spectroscopy (SERS) highlights among others because of its low detection limits and its application fields in the analysis of solid samples. The functionalization of SERS substrates allows to prevent the sorption of undesired molecules of the matrix that can produce additional Raman peaks. A reflective substrate, normally formed of metallic nanoparticles provides a platform able to achieve detection limits of 1010 –1011 , much higher than regular Raman spectroscopy (even at the molecular level) [187–189]. Sonochemically synthetized SERS substrates are inexpensive and fast prepared, and they have been consequently investigated over the last years [190–199]. For instance, Zhang et al. [194] synthetized a hybrid of gold nanoparticles and carbon nanosheets obtaining an enhancement factor of 1.2 × 106 in a very simple and fast method using 4-aminothiophenol as the probe molecule, in one step. In another outstanding example, Wang et al. synthetized a very cheap and efficient substrate, depositing gold nanoparticles over the surface of egg-shell membranes. They tested substrate efficiency in the detection of 4-mercaptopyridine and rodhamine 6 G, showing detection limits as low as 5 × 10−9 M and 1 × 10−6 M, respectively.

Besides, SL has potential to be applied for quantification purposes. As an example, Yurchenko et al. [200] studied the SL of several metallic salts and concluded that SL emission, or SL spectroscopy (as they are named) under adequate calibration was more accurate than atomic absorption to quantify those salts at very high concentration. SL spectroscopy might find utility in the future also in intricate environments where radiation is difficult to host or might affect the reaction conditions. Though it is not an application in the Analytical Chemistry field, sonochemistry has also helped in other type of spectroscopic techniques that use nanoparticles for their measurements, especially as contrast agents in magnetic resonance imaging (MRI) [201–203]. MRI have become a fundamental technique is medical diagnosis and research [204,205]. The development of nanotechnology opened a new observation space, allowing researchers to witness processes never seen before [205]. US has shown already high efficiency in the synthesis of contrast agents as, for instance, the synthesis of nanoparticles of magnetite coated with chitosan with excellent results [202]. 4.1.3. Sensors The construction of a sensor requires two distinct features: a recognition and a transducer element. The first of them is necessary to obtain the desired selectivity and specificity (employing an antibody, an aptamer, a peptide, etc.) while the second converts the biological response into a detectable signal. The previously commented explosion of nanoparticle science has also meant a big transformation in the concept and design of chemical sensors, especially because organic-inorganic nanoparticles are promising candidates for signal transducers. Miniaturization, new detection limits, robustness and/or resilience to adverse conditions (weather, corrosion, etc.) are also some of the main advantages that offers working in the nanoscale space [206]. Some of those materials are also relatively cheap, which is of additional value. The ability of US cavitation to produce nanoparticles in-situ, in one-step synthesis and in very small volumes of liquids have been exploded in the last years in the design of several types of sensors (see Table 2). In fact, the development of electrochemical sensors at nanoscale through sonochemical routes have been the most extended application of sonochemical synthesis in recent years, as it is evidenced from the high number of publications in the topic. The reason has probably been the fact that high surface-to-volume ratios are obtained, as well as a high porosity, which is highly convenient for this type of measurements [176,249]. Table 2 shows a good number of examples found in the literature of the sensors based on nanostructures synthetized by sonochemistry in the last two years. As can be seen, US has been extensively applied to assist the synthesis of many types of nanostructures used to build electrochemical sensors [194–219] (poten-

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Table 2 Sensor based on sonochemically-synthetized nanostructures.

Type of sensor

Analyte(s)

Matrix

Sample treatment

Type of nanoparticle

LOD

References

Human and rat serum

PBS (pH7.0) 1:4

[207]

Glucose

Blood

445.7 nM

[208]

Nitrite

Food samples

0.1 M PBS (pH 7.4) 1:5 dilution pH 5

6.6 nM

[209]

Serotonin

Human serum

0.05 M PBS

12.4 nM

[171]

Paracetamol

Tablet samples

–

9.8 nM

[210]

Morin

Fruit samples

PBS (pH 7.0)

4 nM

[211]

Dicyclomine hydrochloride

Pharmaceutical and biological samples

4.8 nM

[212]

Bacteria

Biological samples

0.04 M Britton Robinson buffer (pH 7.5) –

Bismuth (III) oxide decorated reduced graphene oxide nanocomposite Au decorated core-shell structured Au@Pt Calcium Ferrite (CaFe2 O4 ) clusters modified screen printed carbon electrode Ag/polypyrrole/Cu2 O nanocomposite Nitrogen doped lanthanum metal oxide with reduced graphene oxide sheets Hexamine cobalt(iii) coordination complex grafted reduced graphene oxide composite Carbon electrode modified with silver decorated Fe3 O4 nanocubes Nano-decorated multi-functional electrode Calcium ferrite (CaFe2 O4 ) clusters modified screen printed carbon electrode Strontium molybdate nanoparticles

2.4 nM

Electrochemical

Hormone (epinephrine)

Electrochemical Electrochemical

Electrochemical Electrochemical

Electrochemical

Electrochemical

Electrochemical Nitride

Red wine

0.05 M PBS

Chlorpromazine

Tablet and human urine

PBS

Electrochemical

Neurotransmitter (dopamine) Calcium channel antagonists nifedipine Nitrofurantoin

Human Blood and urine, serum

–

Electrochemical

Iron oxide nanoparticle decorated graphene sheets,

Urine, lake water and commercial NDF tablet

0.05 M PBS; urinecentrifugation

Blood, serum, and urine Human serum and pharmaceutical samples Tablet (Entadoram 100 mg) River Water

Filtered (glass filter), 0.1 HClO4 , cation-exchange SPE 0.1 M NaOH, 1:3 dilution with deionized water 0.1 M PBS (pH 7.0)

Electrochemical

Electrochemical

Electrochemical Electrochemical

Electrochemical

Dopamine and paracetamol Entacapone, levodopa and carbidopa Chromium (VI)

Electrochemical

Glucose

Human blood serum, urine and saliva

Glutathione tablets

Tablets

Cu (II)

Pear fruits

Antibodies

Electrochemical

Ethyl glucuronide Hydrogen peroxide

Electrochemical

Chlorpromazine

Electrochemical

Electrochemical

Electrochemical

Electrochemical

Mercury (II)

Milk and urine samples Pharmaceutical drug WINSUMIN (12.5 mg) and urine samples Tap and river waters

Electrochemical

[214]

0.1–143 and 153– 1683 μM and 0.028 μM 3 nM

[215]

Sphere-like strontium cerate nanoparticles (SrCeO3 nanoparticles)

5 nM

[217]

1:9 dilution with 0.05 PBS (pH 6) PBS

β -cyclodextrin-carbon

1.8 nM

[218]

nanofiber composite Pectin stabilized graphene nanosheets hydrogel

1.5–1.8 nM

[219]

PBS

Praseodymium molybdate nanoplates/reduced graphene oxide nanocomposite Gold nanoparticles graphene oxide electrode

<1 nM

[220]

10 nM

[221]

Sulphur doped reduced graphene oxide supported CuS nanoparticles Silver nanoparticles anchored reduced graphene oxide nanosheets Amino-functionalized graphene/chitosan composite

32 nM

[222]

100 nM

[223]

–

[224]

Zinc oxide nanoflakes

338 μg/L

[225]

Grass-like vanadium disulphide nanostructure 1D β -stannous tungstate nanorods

26 nM

[226]

3 nM

[227]

0.42 nM

[228]

8 nM

[229]

N2 saturated 0.05 M buffer (pH 7) pH 7.4 0.1 M NaOH PBS (pH 7.0)

0.1 M PBS

Electrochemical Riboflavin

Commercial tablets and powders

Deionized water

Caffeic acid

Red wine and soft drink

PBS

Electrochemical

[213] 10−105 cfu/mL 48 nM

Cupric oxide/poly vinyl alcohol nanocomposite Nitrogen - doped carbon quantum dots/SnO2 nanocomposite Graphene oxide sheets supported Cu2 S nanodots

0.22 nM

[216]

[230]

(continued on next page)

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13

Table 2 (continued) Type of sensor

Analyte(s)

Matrix

Sample treatment

Type of nanoparticle

LOD References

2, 4, 6trichlorophenol

Agricultural soil samples

Optical

Nereistoxin insecticides

Environmental

Optical

Cr (VI)

Industrial wastewater

Dried, sieved, centrifuged and pH 5 0.5 mL of 2.5 M NaOH, 1 g of anhydrous sodium sulfate 1 mL of ethyl acetate and was shaken –

Optical

Al (III)

Synthetic samples

–

Optical

Latent fingerprints Cu (II)

LFPs

UV 254 nm

Water solution

LFPs

Synthetic metal cation samples in aqueous solutions –

Wound dressings

Living cells Immunoassay

Electrochemical

Optical

Optical

Optical

Biosensor Biosensor Biosensor Biosensor

Biosensor

Latent fingerprints/lip prints Human neutrophil elastase (HNE) Pb (II) Staphylococcus aureus Glucose Amalgambased mercury (II) Celecoxib

Biosensor

Biosensor Gas sensor

Gas sensor Gas sensor

SGOx-NFs (100 mg/L) and 50 μM AUR Tap water, wastewater

Human plasma sample

Human perspiration Ethylglucuronide and lactate Bilirubin Volatile organic compounds Butane H2

Recovered silver oxide nanoparticles from the wastewater of photo film Gold nanoparticles

–

[231]

–

[232]

2.5 nM

[233]

18 μM

[234]

–

[235]

Ce(III) coordination supramolecular compound

–

[236]

Hollow/solid BaTiO3 :Dy3+ microspheres

3 μM

[237]

–

Hollow/solid BaTiO3 :Dy3+ microspheres

–

[238]

PBS PBS, centrifugation PBS 10 mM, pH 7

Ag nanoclusters ZIF-8/Fe3 O4 hybrid nanoparticles Protein copper nanoflowers

0.2 nM 300 cfu/mL

[239] [240]

3.5 μM

[241]

Deionized water, NaBH4 solution

Nanofibers decorated with gold nanoparticles

1.1 nM

[242]

0.5 mL HClO4 2.0 M, centrifugation –

Silver-choline chloride modified graphene oxide

2.5 nM

[243]

ZnO nanoflakes-based

4.5 μM and 10 pM

[244]

Functionalized cyclodextrin Au-Fe nanoparticles Dihydro-tetrazine functionalized MOF Red lum agent

Human biofluids Synthetic mixes of organic vapours in air

– –

Imine MIL-53(Cr-Fe)/Ag/CNT nanocomposite

2.8 ppm 30.5 ppm

[245] [246]

Air Air

– –

SnO2 /Graphene nanocomposite SnO2 nanoparticles

– –

[247] [248]

AUR: Amplex UltraRed; CNT: carbon nanotube; GOx: glucose oxidase; LFP: latent fringerprint; MIL: Material of Institute Lavoisier; MOF: metal-organic framework; NFs: nanoflowers; PBS: phosphate buffer saline; UV: ultraviolet; ZIF: zeolite imidazolate framework.

tial for both quantitative and qualitative analysis) and optical sensors [220–226], which is a broad classification, including biosensors [227–233] and gas sensors [234–237]. Such nanostructures include MOFs [234,250], bimetallic nanoparticles [215,233,245] or polymer nanocomposites [218,251] among others. Apart from the previously mentioned works, there should be also highlighted several approaches in which US has also been used to synthesize polymeric materials for sensors applications, as previously commented. This includes the use of molecular imprinted polymer nanocomposites [252,253] or polymer coated nanoparticles [251,254], among others. 5. Conclusions Since their discovery, US has been successfully applied in a wide variety of fields, including Analytical Chemistry in which further uses have been identified. Of particular importance has been their application to assist classical extraction procedures, for which they have provided excellent and reproducible results, in most cases without really knowing the extraction mechanism. Classical

extraction applications have also been extended to microextraction procedures in which they play a very important role enhancing in most cases the extraction performance. Even though, it should be taken into account that US does not work equally in all solutions, that it will not enhance all chemical process and that cavitation effects strongly depends on the liquid properties and the gas content. However, it is clear that the current binomial SonochemistryAnalytical Chemistry is beyond that classical view (classical UAE procedures) and that such combination is of high values and is still being used in a good number of works; in fact, current revision of the literature suggests an exponential growth of the number of works in the last years. Of particular importance is the fact that researchers of all disciplines have investigated in the last years US abilities to obtain green and efficient nanostructures as well as polymeric materials, among others, since US application is able to provide new and challenging synthetic routes. Sonochemistry might help in a great manner in separation techniques research, as a green tool that is able to obtain nanoparticles and nanostructures of diverse nature

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faster than others and at room temperature and pressure, reducing also cost and contamination. In addition, the method offers the possibility of changing particle properties (geometry, porosity) and modifying or tuning nanostructures in-situ in diverse environments or over different substrates. Total characterization of US synthesized nanoparticles (size, structure, porosity, BET surface area…) and very often their adsorption capacity (in terms of N2 or CO2 adsorption tests) have been mainly studied, including the ability of some of them to remove water contaminants, among other analytes. Judging from these works, it is clear that US-assisted synthesis of nanoparticles enhances their surface-to-volume ratio, porosity, etc. which is advantageous for their further uses as, for example, extraction sorbents or as part of sensors. However, and contrary to what it may seem, little is known about the improved selectivity of these structures towards the extraction of different target compounds and further works are needed to deepen on this issue, specifically in sorbent-based extraction techniques. That is not the case of their application in sensors, in which US has gained a clear place over last years. Spectroscopy is another field in which US is gaining importance. In all spectroscopic techniques where nanomaterials have become fundamental, as SERS or MRI, sonochemistry is applied to obtain better nanoparticles in a faster, eco-friendly and a more economical way. The potential of SL as radiation emitting source is just symbolically mentioned in literature and has all the future above to obtain spectroscopic information in dark or not accessible environments, or in very concentrated solutions. Despite this promising future of US cavitation, in our opinion, there is still a lack of monitoring the real effects of US in some of these processes, especially in those that can be affected by the presence of water sonolysis products or other radicals, though efforts have also been made to try to understand the way in which US enhances or affects certain analytical procedures. Proper devices and suitable optimization of all US conditions should be carefully taken into consideration. This knowledge will be pursued and consider fundamental if sonochemical processes, with radical formation becomes part of the routine in the laboratory as sample preparation stages are. Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. Acknowledgments C.C. would like to thank the Canary Agency of Economy, Industry, Trade and Knowledge (ACIISI) of the Canary Islands’ Government for the contract to support research activities of the International Research Campus (CEI) of the University of La Laguna. J.G.S. would like to thank “Cabildo de Tenerife” for the Agustín de Betancourt contract at the Universidad de La Laguna. The support of the Fundación CajaCanarias (project 2016TUR07) is also granted. Supplementary materials Supplementary material associated with this article can be found, in the online version, at doi:10.1016/j.chroma.2019.460511. References [1] K.S. Suslick, Sonochemistry, Science 247 (1990) 1439–1445, doi:10.1126/ science.247.4949.1439. [2] J.P.L.T.J. Mason, General principles, in: T.J. Mason, J.P. Lorimer (Eds.), Applied Sonochemistry: Uses of Power 35 Ultrasound in Chemistry and Processing, 2002.

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