A new NIR-emissive fluorescence turn-on probe for Hg2+ detection with a large Stokes shift and its multiple applications

Journal Pre-proof A new NIR-emissive fluorescence turn-on probe for Hg2+ detection with a large Stokes shift and its multiple applications Lijun Tang, Lei Zhou, Xiaomei Yan, Keli Zhong, Xue Gao, Jianrong Li

PII:

S1010-6030(19)31096-2

DOI:

https://doi.org/10.1016/j.jphotochem.2019.112160

Reference:

JPC 112160

To appear in:

Journal of Photochemistry & Photobiology, A: Chemistry

Received Date:

27 June 2019

Revised Date:

29 September 2019

Accepted Date:

11 October 2019

Please cite this article as: Tang L, Zhou L, Yan X, Zhong K, Gao X, Li J, A new NIR-emissive fluorescence turn-on probe for Hg2+ detection with a large Stokes shift and its multiple applications, Journal of Photochemistry and amp; Photobiology, A: Chemistry (2019), doi: https://doi.org/10.1016/j.jphotochem.2019.112160

This is a PDF file of an article that has undergone enhancements after acceptance, such as the addition of a cover page and metadata, and formatting for readability, but it is not yet the definitive version of record. This version will undergo additional copyediting, typesetting and review before it is published in its final form, but we are providing this version to give early visibility of the article. Please note that, during the production process, errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. © 2019 Published by Elsevier.

A new NIR-emissive fluorescence turn-on probe for Hg2+ detection with a large Stokes shift and its multiple applications LijunTang,a,* Lei Zhou,a XiaomeiYan, c KeliZhong,a XueGao,b Jianrong Lib,* a

College of Chemistry and Chemical Engineering, Bohai University, Jinzhou, 121013,

China. E-mail: [email protected] (L. Tang) b

College of Food Science and Technology, Bohai University; National & Local Joint

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Engineering Research Center of Storage, Processing and Safety Control Technology for Fresh Agricultural and Aquatic Products; The Fresh Food Storage and Processing

Technology Research Institute of Liaoning Provincial Universities, Jinzhou, 121013,

Graphical abstract

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College of Laboratory Medicine, Dalian Medical University, Dalian 116044, China

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c

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China. E-mail: [email protected] (J. Li)

A fluorescence off-on Hg2+ probe with near-infrared emission and a large Stokes shift

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as well as its multiple applications have been reported.

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Highlights 

A new fluorescence off-on Hg2+ probe (HBTD-M) with NIR emission and a large Stokes shift has been developed.



HBTD-M can detect Hg2+ with high selectivity and sensitivity.



HBTD-M is capable of imaging Hg2+ in living MCF-7 cells.



HBTD-M is applicable to detect Hg2+ in real water, soil, and seafood samples.

Abstract A novel fluorescence off-on Hg2+ probe with near-infrared (NIR) emission (680 nm)

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and a large Stokes shift (240 nm) has been developed. In MeCN/H2O (1/1, v/v,

HEPES (N-2-hydroxyethylpiperazine-N-ethane-sulphonic acid) 10 mM, pH = 7.4)

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solution, (E)-O-(2-(benzo[d]thiazol-2-yl)-4-(2-(3-(dicyanomethylene)-5,5-dimethylc-

yclohex-1-en-1-yl)vinyl)-6-methylphenyl)-O-phenyl carbonothioate (HBTD-M) can

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detect Hg2+ with high selectivity and sensitivity. The sensing mechanism is based on

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releasing

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Hg2+-triggered cleavage of carbonothioate moiety in probe HBTD-M, which results of

its

precursor

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(E)-2-(3-(3-(benzo[d]thiazol-2-yl)-4-hydroxy-5-methylstyryl)-5,5-dimethylcyclohex2-en-1-ylidene)malononitrile (HBTD). In addition, HBTD-M has been successfully

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used to detect Hg2+ in real water, soil, and seafood samples with good recoveries and

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small relative standard deviations. Keywords: Fluorescent probe; Near-infrared emission; Large Stokes shift; Hg2+ detection; Water examples; Seafood 1. Introduction Mercury ion (Hg2+) is considered to be one of the most harmful heavy metal ions to human health and the ecological environment because of its high toxic, easy 2

absorptivity and high bioaccumulation.1, 2 Studies revealed that excessive Hg2+ can result in substantial damage to the nervous system and endocrine system, 3, 4 and can lead to diseases such as insomnia, memory loss, hemoptysis, difficulty breathing, etc. Therefore, effective detection of Hg2+ is of great importance. Currently, there are several methods for Hg2+ detection including atom absorption spectroscopy,5

differential

pulse

anodic

stripping

voltammetry6,

capillary

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electrophoresis7, etc. have been established. However, these methods have the disadvantages of sophisticated instrumentation, complicated operation, difficult

pre-treatment and time consuming. In this case, the fluorescence technique has

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attracted a dramatically increasing attention due to its merits such as high sensitivity,

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high selectivity, simple operation and low cost.8, 9 During the past decades, a huge number of fluorescent probes for Hg2+recognition have been reported.10-17 Whereas,

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most of the reported Hg2+ probes possess the defects of short emission wavelength or

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small Stokes shift, which severely restricted their practical applications, especially in bioimaging. Fluorescent probe with near-infrared (NIR) emission has the advantages

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of low photo damage, deep tissue penetration, and little effect from background auto-fluorescence, and has been proved to be more suitable for bioimaging. 18 On the

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other hand, fluorescent probe with a large Stokes shift can effectively reduce self-absorption and self-luminescence of the probe, which can greatly improve the detection accuracy and spatial resolution for bioimaging. It is noteworthy that only a few fluorescent probes display both NIR emission and a large Stokes shift have been documented.19-22 Therefore, development of Hg2+ specific fluorescent probe with

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NIR-emission and a large Stokes shift is still an appealing task. Some

recent

studies

demonstrate

that

rational

modification

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2-(2-hydroxyphenyl)benzothiazoles (HBT) is a promising approach to obtain far-red or NIR-emissive fluorescent probes with a mega Stokes shift. 23-28 HBT is well-known for its excited-state intramolecular proton transfer (ESIPT) feature,29-31 which is favorable to result in a large Stokes shift; Many previous work also revealed that

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extending the π-conjugation of HBT in the para- or ortho-position of the phenol group with a strong electron withdrawing group is favorable to the ESIPT event, which is promising to lead to far-red or NIR emission with the aid of intramolecular charge

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transfer (ICT) effect.26,32 The dipole moment of the fluorophore can be increased

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when the ICT effect in the molecule is enhanced, which will resulting in a red shift of its fluorescence emission. Inspired by these existing results, we herein designed and

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synthesized a new HBT derivedHg2+ selective fluorescent probe HBTD-M (Scheme

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1). In the probe, the incorporated carbonothioate moiety acts as Hg2+ recognition group.33 The conjugated dicyanoisophorone moiety extends the π-conjugation system

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and acts as a strong electron withdrawing group, which can elicit a strong ICT effect and enable the desired long wavelength emission. Further studies show that probe

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HBTD-M exhibits high selectivity toward Hg2+ with NIR emission (680 nm) and a large Stokes shift (240 nm). HBTD-M is applicable to image Hg2+ in living MCF-7 cells and detect Hg2+ in soil, water, and seafood samples.

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Scheme 1. Synthesis of probe HBTD-M. 2. Experimental

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2.1 Materials and instruments

All analytical reagents and solvents were purchased from commercial suppliers and

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can be used without further purification unless otherwise stated. Dry dichloromethane

was prepared by treating commercial dichloromethane with CaH2. Compounds 123 and

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234 were synthesized by the methods reported in the literature. MCF-7 (human breast

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carcinoma) cells were purchased from Institute of Basic Medical Sciences (IBMS) of Chinese Academy of Medical Sciences (CAMS). 1H NMR and 13C NMR spectra were in

deuterated

solvents

with

an

Agilent

400-MR

spectrometer.

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recorded

High-resolution mass spectroscopy (HRMS) was obtained on a Bruker micrOTOF-Q

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mass spectrometer (Bruker Daltonik, Bremen, Germany). UV-vis absorption spectra

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were measured on a SP-1900 spectrophotometer (Shanghai Spectrum instruments Co., Ltd., China). Fluorescence spectra were measured with a 970CRT fluorescence spectrophotometer (Shanghai Spectrometer Co., Ltd., China). Fluorescence quantum yields and fluorescence lifetime were measured on a stable/transient FLS 1000 fluorescence spectrometer (Edinburgh, U.K.). pH measurements were conducted with an PHS-25B meter (Shanghai DaPu Instrument Co., Ltd., China). Cell imaging 5

experiments were acquired using an Olympus IX-71 inverted microscope (Olympus, Tokyo, Japan). 2.2 Synthesis of HBTD To a solution of compounds 1 (1.35 g, 5.0 mmol) and 2 (1.12 g, 6.0 mmol) in 20 mL of absolute ethanol, two drops of piperidine were added. The mixture was heated under reflux for 6 h. After cooling to room temperature, the precipitates were

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collected by filtration and washed with cold ethanol to give HBTD in a yield of 83%.

m.p. 284.0-286.0 oC. 1H NMR (400 MHz, CDCl3) δ 13.17 (s, 1H), 8.00 (d, J = 8.1 Hz,

1H), 7.94 (d, J = 8.1 Hz, 1H), 7.58-7.41 (m, 4H), 7.04 (d, J = 16.0 Hz, 1H), 6.93 (d, J

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= 16.0 Hz, 1H), 6.86 (s, 1H), 2.61 (s, 2H), 2.49 (s, 2H), 2.39 (s, 3H), 1.10 (s, 6H); 13C

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NMR (100 MHz, CDCl3) δ 154.6, 151.5, 134.0, 133.6, 132.5, 131.4, 131.2, 130.8, 129.8, 129.0, 128.8, 126.9, 125.8, 124.5, 124.2, 123.5, 122.0, 121.6, 78.2, 43.0, 42.7,

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Found: 436.1465.

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39.1, 32.1, 28.0, 27.6, 20.5. HRMS (ESI-): Calcd for C27H22N3OS [M-H]-, 436.1484;

2.3 Synthesis of HBTD-M

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HBTD (1.30 g, 3.0 mmol) was dissolved in 20 mL of dry dichloromethane at 0 oC, triethylamine (0.454 g, 4.5 mmol) and phenyl carbonochloridothioate (0.621 g, 3.6

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mmol) were added and stirred for further 0.5 h, then the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was purified by silica column chromatography (dichloromethane/petroleum ether = 1/1, v/v) to give HBTD-M as yellow solids (0.802 g, 47%). m.p. 214.0-214.9 C. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (s, 1H), 8.29 (d, J = 7.9 Hz, 1H), 8.14 (d, J

o

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= 8.1 Hz, 1H), 8.01 (s, 1H), 7.62 (t, J = 7.7 Hz, 1H), 7.59-7.52 (m, 3H), 7.52 (d, J = 16.2 Hz, 1H), 7.46 (d, J = 16.2 Hz, 1H), 7.39 (t, J = 7.2 Hz, 1H), 7.31 (d, J = 7.9 Hz, 2H), 6.96 (s, 1H), 2.63 (s, 2H), 2.57 (s, 2H), 2.38 (s, 3H), 1.02 (s, 6H). 13C NMR (100 MHz, DMSO-d6) δ 192.6, 170.8, 161.9, 155.8, 153.5, 152.8, 149.1, 136.0, 135.8, 135.4, 132.9, 131.6, 130.5, 127.4, 126.6, 126.4, 124.0, 123.5, 122.9, 122.0, 77.5, 42.7,

574.1618. 2.4 Sample preparation and optical measurements

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38.6, 27.9, 16.5. HRMS (ESI+): Calcd for C34H28N3O2S2 [M+H]+, 574.1623; Found:

Stock solution of HBTD-M (1 mM) was prepared in DMSO, and the tested ions

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(Ni2+, Hg2+, Ba2+, Mg2+, Ag+, Fe2+, K+, Al3+, Mn2+, Ca2+, Mn2+, Pb2+, Sr2+, Co2+, Zn2+,

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Cd2+, Cr3+，Fe3+，Cu2+，Cl-，F-，I-，CO32-，NO3-，SO42-，HSO4-，and H2PO4-) solutions (10 mM) were prepared in double-distilled water. The fluorescence spectra were

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measured in the presence of different doses of analyte in a quartz cuvette at room

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temperature.

2.5 Cell culture and imaging

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MCF-7 cells were cultured in Dulbecco’s modified Eagle’s medium (DMEM, Invitrogen) in the presence of 10% FBS (fetal bovine serum) in an atmosphere of 5%

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CO2 and 95% air at 37 oC. Grow MCF-7 cells in the exponential phase of growth on 35-mm glass-bottom culture dishes ( 20 mm) for 1 to 2 days to reach ca. 80% confluence. After the culture medium was discarded, the cells were washed three times with phosphate-buffered saline (PBS) (pH = 7.4). The cells were further incubated with HBTD-M (10 M) for 30 min at 37 oC in the presence of 1 mM

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hexadecyltrimethylammonium bromide (CTAB, a surfactant that was used to increase the solubility of the probe).Then the cells were washed three times with PBS buffer and conducted cell imaging. To evaluate the capability of HBTD-M for Hg2+imaging in living cells, the probe pretreated live MCF-7 cells were in situ incubated with different concentrations of Hg2+ for 30 min at 37 oC, and then the same set of cells was used for fluorescence image measurement.

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3. Results and discussion 3.1 Optical responses of HBTD-M to Hg2+

Firstly, the UV-vis spectral response of the probe toward different metal ions were

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explored in MeCN/H2O (1/1, v/v, HEPES 10 mM, pH = 7.4) solution (Fig. S1).

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Except Hg2+, individual addition of other metal ions induced no or slight absorption spectra changes. On addition of Hg2+, the absorbance of HBTD-M solution is greatly

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decreased (the molar absorptivity changes from 58810 M-1cm-1 to 25523 M-1cm-1).

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Despite this, it will difficult to discriminate whether an observed small absorbance decrease is caused by a large amount of other ions or induced by a small amount of

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Hg2+, which may result in false signals and cause misjudgment. We then examined the fluorescence responses of probe HBTD-M toward different metal ions. In

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MeCN/H2O (1/1, v/v, HEPES 10 mM, pH = 7.4) solution, probe is almost non-emissive when excited at 440 nm ( = 0.66%). Upon addition of 7.0 equiv. of Hg2+, a strong fluorescence emission band centered at 680 nm was observed ( = 11.87%), and the fluorescence life time of HBTD-M+Hg2+ was evaluated to be 0.56 ns (Fig. S2). However, individual addition of other ions (Ni2+, Hg2+, Ba2+, Mg2+, Ag+,

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Fe2+, K+, Al3+, Mn2+, Ca2+, Mn2+, Pb2+, Sr2+, Co2+, Zn2+, Cd2+, Cr3+，Fe3+，Cu2+，Cl-， F-，I-，CO32-，NO3-，SO42-，HSO4 -，and H2PO4-) induced no observable fluorescence enhancement (Fig. 1A), suggesting the high fluorescence selectivity of HBTD-M to Hg2+. To further demonstrate the high selectivity of HBTD-M to Hg2+, competitive experiments were subsequently carried out (Fig. 1B). Amongst various tested metal ions, only Cu2+ interfered with the response of probe HBTD-M to Hg2+. In order to

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inhibit the interference from Cu2+, 1,10-phenanthroline (OP) (a commonly used Cu2+ ion masking agent) was used (Fig. S3). The experimental results showed that the

presence of OP can effectively inhibit the interference of Cu2+, but had little effect on

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the Hg2+recognition event, indicating that the probe still has good application value.

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Meanwhile, we found that the fluorescence spectrum of the HBTD-M (10 μM) after adding 7.0 equiv. Hg2+ was almost identical with that of compound HBTD (10 μM)

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(Fig. S4), suggesting the formation of HBTD after HBTD-M reacted with Hg2+.

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Time-dependent investigation revealed that the Hg2+ recognition process can be

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accomplished within 60 min (Fig. S5).

Fig. 1. (A) Fluorescence spectrum changes of HBTD-M (10 μM) upon addition of 7.0 equiv. of different ions in MeCN/H2O (1/1, v/v, HEPES 10 mM, pH = 7.4). Insert: 9

Fluorescence photographs of the probe solution before and after addition of Hg2+. (B) Fluorescence intensity (at 680 nm) of HBTD-M (10 μM) in MeCN/H2O (1/1, v/v, HEPES 10 mM, pH = 7.4) on addition of various metal ions followed by addition of Hg2+ (metal ions were used as 70 μM). 3.2 Titration experiment of HBTD-M and calculation of detection limit To investigate the sensitivity of probe HBTD-M, we performed fluorescence

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titration experiments (Fig. 2A). Upon progressive addition of Hg2+ to HBTD-M solution, the fluorescence intensity at 680 nm gradually increased and reached a

plateau when 7.0 equiv. of Hg2+ was employed. The fluorescence intensity versus

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Hg2+ concentration (0 to 70 μM) behaved a good linear relationship (Fig. 2B). Based

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on the titration profile, the limit of detection (LOD = 3σ/k)35 of HBTD-M for Hg2+ was calculated to be 1.64×10-7 M, which is better or comparable to that of some

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reported Hg2+ probes (Table S1). Moreover, the results of non-linear least squares

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fitting of the titration profile demonstrate that HBTD-M interacted with Hg2+ through

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a 1:1 stoichiometry (Fig. S6).

Fig. 2. (A) Fluorescence spectrum changes of HBTD-M (10 μM) in MeCN/H2O (1/1, v/v, HEPES 10 mM, pH = 7.4) on incremental addition of Hg2+. (B) Linear

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relationship between emission intensity (680 nm) and the added Hg2+ concentration. 3.3 The effect of pH In order to investigate the practical applicability, we investigated the pH effect on the recognition behavior of HBTD-M to Hg2+ (Fig. 3). HBTD-M exhibits almost non-emissive at 680 nm within the pH range from 2 to 13. In the presence of 7 equiv. of Hg2+, the fluorescence intensity at 680 nm was significantly enhanced at pH

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ranging from 6 to 11, demonstrating that HBTD-M is suitable for Hg2+ detection in a

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wide pH window.

Fig. 3. Fluorescence intensity of HBTD-M and HBTD-M+Hg2+ at different pH

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conditions

3.5 Sensing mechanism

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The previous examinations suggested that the Hg2+-triggered fluorescence signal change of HBTD-M may due to the reaction induced formation of HBTD. To verify our hypothesis, we carried out the reaction of HBTD-M with Hg2+ in MeCN/H2O mixed solution and monitored the reaction by thin layer chromatography. As shown in Fig. S7, a reaction product with Rf (the ratio of the distance from the origin to the center of the spot in thin-layer chromatography versus the distance from the origin to 11

the front of the eluent) similar to that of HBTD can be observed, providing a preliminary evidence for our conjecture. HRMS analysis of the reaction mixture of HBTD-M with Hg2+ showed a peak at m/z = 436.1491 (Fig. S8), which is assignable to HBTD [M-H]- (Calcd. m/z =436.1484). Furthermore, the reaction product was separated and its 1H NMR spectrum was compared with that of HBTD and HBTD-M. The results show that the isolated product and compound HBTD have identical 1H NMR spectrum (Fig. 4), supplying a solid evidence for the formation of HBTD

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(Scheme 2).

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Scheme 2. The detection mechanism of probe HBTD-M for Hg2+

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Fig. 4. Partial 1H NMR spectra comparison of HBTD-M in DMSO-d6 (A), isolated product from reaction of HBTD-M+Hg2+ in CDCl3 (B), and compound HBTD in

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CDCl3 (C).

3.6 Imaging of Hg2+ in living cells

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Inspired by the good sensing performance of HBTD-M to Hg2+, we then explored its application to image Hg2+ in living cells. According to the cytotoxicity test data,

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the toxicity of probe HBTD-M towards MCF-7 cells is very small (Fig. S9), so

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MCF-7 cells were used to perform live cell imaging experiments. MCF-7 cells were first incubated with HBTD-M(10M) for 30 min at 37 oC, and no fluorescence emission can be observed from confocal laser scanning microscope within the red channel on excitation at 405 nm (Fig. 5E). Then the probe pretreated MCF-7 cells were washed three times with PBS buffer, and further incubated with varied concentrations of HgCl2 (10, 30, and 50 M) for 30 min, obvious red fluorescence can

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be observed, and the brightness of the fluorescence increased with increasing the Hg2+ concentration (Fig. 5F, G, H). These results show that HBTD-M is capable of

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imaging Hg2+ in living MCF-7 cells.

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Fig. 5. Confocal fluorescence images of MCF-7 cells incubated with HBTD-M (10M) followed by incubation with and 0 M (A, E), 10 M(B, F), 30 M (C, G)

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and 50 M (D, H) of Hg2+ions. Left column: bright field images. Right column: dark field images. ex= 405 nm.

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3.7 Detection of Hg2+ in real water, soil and seafood samples

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To further confirm the potential applicability of HBTD-M, detection of Hg2+ in real water, soil, and seafood samples were explored. Each pretreated sample (please see supplementary data for detailed treatment procedures) was firstly mixed with CH 3CN (1/1, v/v) and spiked with different concentrations of Hg2+. Then 10 M of probe was added into each sample and the fluorescence spectrum was measured. It can be seen from Figs. 6 and 7 that in real water, soil and seafood samples, the observed 14

fluorescence intensity (at 680 nm) and spiked Hg2+ concentration (0-70 μM) display a good linear relationship, indicating that detection of Hg2+ can be achieved within this concentration range. Thus the probe can be applied to detect Hg2+in real water, soil and seafood samples. As shown in Table 1, the calculated recoveries ranging from 93.7% to 108.5%, the relative standard deviations (RSDs) are less than 5.84%, and the

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real samples, and the strategy is reliable and feasible.

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relative error are less than 8.5%. Therefore, HBTD-M is applicable to detect Hg2+in

Fig. 6. Linear relationship between fluorescence intensity and the spiked Hg2+

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concentrations in real water and soil samples.

Fig. 7. Linear relationship between fluorescence intensity and the spiked Hg2+ concentrations in seafood samples. 15

Table 1. Application of HBTD-M in determination of Hg2+ in actual samples Detect ( μM) 21.4 48.9 69.7

RSD (%) 4.65 3.73 4.06

Recovery (%) 107.0 97.8 99.6

Relative error (%) 7.0 2.2 0.4

Lake Water

20 50 70

21.0 50.0 70.1

3.87 2.37 2.33

105.0 100.0 100.1

5.0 0 0.1

Soil

20 50 70

18.8 47.9 73.0

5.84 3.95 4.16

94.0 95.8 104.3

6.0 4.2 4.3

Fish

20 50 70

19.5 47.3 72.8

2.47 3.76 1.37

97.5 94.6 104.0

2.5 5.4 4.0

Shrimp

20 50 70

18.7 49.2 72.1

4.51 2.98 3.65

93.5 98.4 103.0

6.5 1.6 3.0

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*Average data of three replicates.

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River water

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Added (μM) 20 50 70

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Sample

Conclusion

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In summary, we have developed a HBT-derived fluorescence turn-on probe HBTD-M forHg2+ recognition in MeCN/H2O (1/1, v/v, HEPES 10 mM, pH = 7.4)

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solution with NIR emission and a large Stokes shift. The Hg2+ recognition process by

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HBTD-M holds high selectivity and sensitivity with a detection limit of 1.64×10-7 M. The Hg2+ recognition mechanism investigation reveal that HBTD-M undergo Hg2+-induced cleavage of carbonothioate moiety to release its precursor HBTD. Moreover, probe HBTD-M is capable of imaging Hg2+ in living MCF-7 cells, and is applicable to detect Hg2+ in real water, soil, and seafood samples with good recoveries

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and small relative standard deviations. Conflict of Interest The authors declare that they have no conflicts of interest to this work.

Acknowledgments The project was supported by the National Natural Science Foundation of China (Nos. 21878023, U1608222 and 21304009), the LiaoNing Revitalization Talents Program,

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the Natural Science Foundation of Liaoning Province (20170540019), and the Doctoral Scientific Research Foundation of Liaoning Province (No. 20170520416). Supplementary data

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