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Three new coordination polymers based on an N-heterocyclic carboxylic acid: Structural diversity, luminescent properties and gas adsorption
Journal of Solid State Chemistry 280 (2019) 120916
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Three new coordination polymers based on an N-heterocyclic carboxylic acid: Structural diversity, luminescent properties and gas adsorption Jinfang Liang, Jinxia Liang, Lijun Zhai, Haonan Wu, Xiaoyan Niu, Jie Zhang *, Tuoping Hu **
A R T I C L E I N F O
A B S T R A C T
Keywords: N-Heterocyclic aromatic carboxylic acid Coordination polymers Luminescent quenching Gas adsorption Quenching mechanism
Based on a mixed-ligand strategy, three new coordination polymers (CPs), namely {[Zn2(TZMB)2(bim)]⋅2DMA⋅EtOH}n (1), {[Zn2(TZMB)2(4,40 -bibp)⋅2DMA⋅EtOH]}n (2), and {[Cd(TZMB)(bbibp)] DMA⋅EtOH}n (3), (bim ¼ benzimidazole, 4,40 -bipb ¼ 4,40 -bis(pyrid-4-ly)biphenyl, bbibp ¼ 4,40 -bis(benzoimidazo-1-ly)biphenyl, DMA ¼ N, N-dimethylacetamide), have been successfully synthesized by the reaction of 4,4'-(1H-1,2,4-triazol-1yl)methylenebis (benzonic acid) (H2TZMB) and Zn(II)/Cd(II) under the solvothermal methods. The structural analyses indicate that 1 displays 2-nodal (3,4)-c 3D framework with a {63}{65.8} topology, 2 exhibits a rare 1D þ 1D → 3D framework with the same topology as 1, and 3 is a 3D supramolecular framework obtained by π … π stacking interaction between the adjacent 2D layers with the topology of {65.8}. Furthermore, the luminescent experiments indicate that 1 and 2 exhibit high sensitivity and selective detection towards Fe3þ ions with the low detection limit of 7.15 104 M1 and 2.56 104 M1, respectively. Gas adsorption behaviors show the adsorption amounts of 3a for CO2 advantage over those of CH4 and N2. The selectivities of 3a for CO2/CH4 were estimated by the ideal adsorbed solution theory (IAST), which are 4.78 for land fill gas (CO2:CH4 ¼ 0.50:0.50) and 1.39 for natural gas (CO2:CH4 ¼ 0.05:0.95), respectively. Finally, the luminescent quenching mechanisms are also discussed in detail.
1. Introduction Coordination polymers (CPs) have always been the focus of researchers in the past few years, which possess diverse architectures and complicated topologies as well as were widely used in the fields of luminescent detecting [1,2], gas adsorption/separation [3,4], catalysis [5]. With the progress of human society and heavy industry, a mass of toxic organic small molecules and hazardous metal ions are being discharged into environment and have posed many negative effects on human's health. Iron ion is essential in the process of metabolism, such as the formation of hemoglobin, muscular and brain growth, and the building-up process of RNA and DNA [6–8]. Both deficiency and overload of iron can pose serious health disorders such as insomnia, weakened immunity and skin diseases [9,10]. Therefore, it is highly urgent to detect Fe3þ ions [11-13]. Continuous research and efforts to address these issues by utilizing the traditional means, for instance, mass spectrometry (MS) [14], atomic absorption spectrometry (AAS) [15], ion mobility spectrum [16], gas chromatography and cyclic voltammetry [17,18] are often unsatisfactory. Because these modern analysis and technology have some
unavoidable pitfalls, such as high cost, fussy preparation phase, complex procedure and long response time. Hence, it is necessary to explore an efficient, convenient, low-cost and recyclable approach to track contaminants quickly. Nevertheless, on account of their high selectivity and sensitivity, recyclability and visualization, CPs have been deemed as one of more potential luminescent detectors to detect pollutants. What's more, some CPs own large surface area, modifiable tunnel, which give them great application prospect in areas of gas adsorption, storage and separation [19–21]. [19–21]. As we all known, carbon dioxide (CO2), as a persistent increasing greenhouse gas, primarily comes from burning of more and more fossil fuels [22,23]. The greenhouse effect can give rise to abnormal climate change and sea level rises. Hence, it is quite significant to seek material for capturing CO2 in order to alleviate the greenhouse effect and improve the environment quality. Compared to other porous materials, such as zeolite materials [24], organic polymers [25], CPs have the advantages of high stability and porous structure, which make them become functional materials for capture and separation of CO2 [26–31]. Therefore, designing and synthesizing novel multifunctional materials to detect contaminants are imminent for sustainable development and
* Corresponding author. ** Corresponding author. E-mail addresses: [email protected] (J. Zhang), [email protected] (T. Hu). https://doi.org/10.1016/j.jssc.2019.120916 Received 30 June 2019; Received in revised form 16 August 2019; Accepted 16 August 2019 Available online 20 September 2019 0022-4596/© 2019 Elsevier Inc. All rights reserved.
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C68H64O11N8Zn2: C, 62.80; H, 4.96; N, 8.61. Found (%): C, 62.85; H, 4.45; N, 8.62. IR (KBr pellet, cm1): 3448 (vs), 2376 (w), 1626 (s), 1558 (s), 1365 (s), 1132 (m), 999 (m), 810 (m), 775 (m), 651 (w), 628 (w), 563 (w).
human health. Therefore, in this work, based on Y-shaped {4,4'-(1H-1,2,4-triazol-yl) methylenebis(benzonic acid)}(H2TZMB) and three different rigid Nheterocyclic ligands (bim ¼ benzimidazole, 4,40 -bipb ¼ 4,40 -bis(pyrid-4ly)biphenyl, bbibp ¼ 4,40 -bis(benzoimidazo-1-ly)biphenyl) (Scheme 1), three new CPs, namely, {[Zn2(TZMB)2(bim)]⋅2DMA⋅EtOH}n (1), {[Zn2(TZMB)2(4,40 -bipb)⋅2DMA⋅EtOH]}n (2) and {[Cd(TZMB)(bbibp)]⋅ DMA⋅EtOH}n (3) have been synthesized under the solvothermal methods. Furthermore, the luminescent properties of 1 and 2, and the gas adsorption behaviors of 3 were also investigated.
2.2.3. Synthesis of {[Cd(TZMB)(bbibp)]⋅DMA⋅EtOH}n (3) The mixed solvent of DMA/EtOH/H2O (4 mL, v/v/v ¼ 1:1:2) was added into the mixture of H2TZMB ligand (0.024 mmol, 7.8 mg), NaOH (0.01 mol/L, 4.8 mL). The above mixture was transferred into a stainless steel vessel (25 mL) containing Cd(NO3)2⋅4H2O (0.012 mmol, 3.7 mg) and bbibp (0.024 mmol, 9.3 mg), which was adjusted to pH ¼ 3 by adding dropwise HNO3 (0.005 mol L1) aqueous solution. The vessel was sealed and heated to 110 C for 3 days and naturally cooled to ambient temperature to get orange-yellow crystals. Yield: 70.23% (based on Cd). Anal. calcd (%) for C49H44N8O6Cd: C, 61.73; H, 4.65; N; 11.75. Found (%): C, 61.74; H, 4.63; N, 11.80. IR (KBr pellet, cm1): 3448 (vs), 2970 (w), 1593 (s), 1506 (s), 1398 (m), 1299 (m), 1134 (m), 1006 (m), 829 (m), 742 (w), 648 (w), 582 (w), 534 (w).
2. Experimental 2.1. Materials and methods All chemical reagents have been purchased commercially and used without further purification. IR spectra were tested by a FTIR-8400s spectrometer with KBr pellet from 500 to 4000 cm1. Powder X-ray diffraction (PXRD) was performed by a diffractometer (Rigaku D/Max2500 PC) with Mo-Kα radiation at room temperature in the range of 5–50 (2θ). The contents of C, N, and H were determined by Vario MACRO analyzer (EA). The UV–vis spectra were performed on a UV2300 analytical instrument. Luminescent spectra were tesed by a F-2700 spectrophotometer. Thermal stability of CPs was measured under a ZCTA instrument from 25 to 800 C under nitrogen flow. Gas adsorption behaviours were evaluated on an ASAP-2020 analyzer.
2.3. Single crystal X-ray crystallography All crystallographic data of CPs 1–3 were obtained on a Bruker Smart CCD diffractometer (Mo-Kα radiation, λ ¼ 0.71073 Å) at 170(1)/273(2)/ 293(3)K. The structures were solved through direct method by means of SHELXTL-2016 program by the full-matrix least-squares method on F2. Crystallographic data and refinement parameters for 1–3 were presented in Table S1, selected bond angles and lengths are shown in Table S2. CCDC: 1917486 (1), 1917487 (2) and 1917488 (3).
2.2. Syntheses of CPs
3. Results and discussion
2.2.1. Synthesis of {[Zn2((TZMB)2(bim)]⋅2DMA⋅EtOH}n (1) NaOH (0.01 mol/L, 0.8 mL) was added into the mixture of the H2TZMB ligand (0.004 mmol, 1.3 mg) and a mixed solvent of DMA/ EtOH/H2O (1 mL, v/v/v ¼ 2:1:1), and then the mixture was transferred into a glass tube containing bim (0.008 mmol, 0.9 mg) and Zn(NO3)2⋅6H2O (0.008 mmoL, 2.4 mg). The glass tube was sealed and heated at 110 C for 3000 min and then naturally cooled to ambient temperature to obtain colorless block crystals. Yield: 88.35% (based on Zn). Anal. calcd (%) for C51H51Zn2N10O11: C, 55.14; H, 4.63; N, 12.61. Found (%): C, 55.02; H, 4.49; N, 12.89. IR (KBr pellet, cm1): 3448 (vs), 2370 (w), 1616 (s), 1558 (s), 1419 (s), 1282 (s), 1122 (s), 995 (m), 842 (m), 756 (m), 649 (m).
3.1. Structural descriptions 3.1.1. {[Zn2(TZMB)2(bim)]⋅2DMA⋅EtOH}n (1) Complex 1 crystallizes in the monoclinic space group C2/m and exhibits a 3D framework. The asymmetric unit includes one Zn(II) ion, one TZMB2 ligand, one bim, one lattice EtOH molecule and two lattice DMA molecules (Fig. 1). The central Zn(II) ion is bonded to three O atoms (O1, O2 and O3A) of two TZMB2 ligands and two atoms (N3, N2B) of one TZMB2 ligand and one bim ligand, respectively. The H2TZMB linker is completely deprotonated and shows a μ3-(κ 1κ 1)-(κ1-κ 1)-(κ1-κ 0) (Scheme 2, Mode III) coordination mode. As displayed in Fig. 2a, every TZMB2 ligand connects two Zn(II) ions to from a {Zn(COO)2} unit, which is linked by bim ligand to build a quasiquadrilateral 2D layer network. Among them, bim ligand as a linker only plays the role of stabilizing the structure. The adjacent 2D layers further interlock to form the 3D framework of 1 (Fig. 2b). By topological analysis performed on TOPOS Software [32], the
2.2.2. Synthesis of {[Zn2(TZMB)2(4,40 -bipb)]⋅2DMA⋅EtOH}n (2) The synthesis process of 2 is the same as l except that bim ligand (0.008 mmol, 0.9 mg) was replaced by 4,40 -bipb ligand (0.008 mmol, 2.5 mg) and the reaction system was adjusted to pH ¼ 4 by dropwise adding HNO3 (0.005 mol L1) aqueous solution. Colorless block crystals of 2 were collected. Yield: 74.12% (based on Zn). Anal. calcd (%) for
Scheme 1. The H2TZMB and N-Heterocyclic ligands. 2
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Fig. 1. Coordination environment of the Zn(II) ion in 1. (symmetry codes: A: 0.5 þ x, 0.5-y, 1þz; B: 0.5 þ x, 0.5-y, z; C: x, 1-y, z. Hydrogen atoms and lattice molecules are omitted for clarity).
Scheme 2. Diverse coordition modes of H2TZMB in 1–3.
whole 3D framework can be simplified to a 2-fold interpenetrated (3,4)-c net with the topology of (63)(65.8) (Fig. 2c), when TZMB2 ligand and {Zn(COO)2} unit can be seemed as 3-c node and 4-c node, respectively. 3.1.2. {[Zn2(TZMB)2(4,40 -bipb)]⋅2DMA⋅EtOH}n (2) Complex 2 crystallizes in the monoclinic space group P2/C. Its repeating unit contains two Zn(II) ions, two TZMB2 linkers, one 4,40 bipb ligand, one lattice EtOH molecule and two lattice DMA molecules (Fig. 3). The central Zn(II) ion is surrounded by two O atoms of two identical TZMB2 ligands [Zn–O ¼ 1.916(8) Å], and two N (N2A, N5) atoms of one TZMB2 ligand [Zn1–N2A ¼ 2.017(8) Å] and one 4,40 bbipb ligand [Zn1–N5 ¼ 2.051(7) Å], respectively, which are similar to those reported for other Zn-CPs (Table S3) [33]. The H2TZMB ligand is completely deprotonatand presents a μ3-(κ 1κ 0)-(κ 1-κ0))-(κ 1-κ 0) (Mode I, Scheme 1) coordination mode. Each TZMB2 ligand connects with three Zn(II) ions to obtain a Y-shaped 1D chain [Zn3-(TZMB)]n, which interconnect each other further to develop a circulating like-hexagon structure (Fig. 4a). Zn(II) ions and TZMB2 ligands are connected with 4,40 -bibp ligands to build another infinite 1D chain [Zn2-(TZMB)-(4,40 -bibp)]n (Fig. 4b). Then, the above two 1D chains interconnect with together to build a 3D framework (Fig. 4c). Topologically, the framework of 2 shows a 2-nodal (3,4)-c 3D framework with the topology of (63)(65.8) (Fig. 4d). According to the above structure analyses, 2 belongs to the third category of one-fold 1D þ 1D → 3D stable framework [34].
Fig. 2. (a) View of the 2D symmetrical quadrilateral channel along the a axis of 1. (b) The two-fold interpenetrating 3D framework of 1. (c) Topology of the 3D network in 1.
obtain a 3D supramolecular network. The cavity volume of 3 is 1221.9Å3 out of the 4920.5Å3 per unit cell volume by PLATON, and the porosity is estimated to be 26.4%. Topologically, the overall 3D supramolecular framework can be regarded as a 2-fold interpenetrated 4-c 3D framework with the topology of (65.8) (Fig. 6c). 3.2. Phase purity, thermal stability and IR spectra analyses
3.1.3. {[Cd(TZMB)(bbibp)]⋅DMA⋅EtOH}n (3) Complex 3 crystallizes in the orthorhombic space group Pnna. As exhibited in Fig. 5, the repeating unit contains one Cd(II) ion, one TZMB2 ligand, one bbibp ligand, one lattice EtOH molecule and one lattice DMA molecules. The central Cd(II) ion is linked by two nitrogen atoms of bbibp ligand [Cd–N ¼ 2.241(2) Å] and four oxygen atoms of two indentical TZMB2 ligands [Cd–O ¼ 2.286(2) Å], presenting a quasitriangular bipyramid geometry. The bond lengths of Cd–O/N are in agreement with that of the previously reported Cd-CPs (Table S3) [35]. The H2TZMB ligands present μ2-(κ 1-κ 1)-(κ1-κ 1) (Mode II, Scheme 1) coordination mode and link Cd(II) ions to construct two identical 2D chains (Fig. 6a). As can be seen from Fig. 6b, the two adjacent 2D networks further catenate with each other through π … π interactions to
The powder X-ray diffraction (PXRD) has been performed at ambient temperature to prove the purity of 1–3, As displayed in Figs. S4–S6, the characteristic peaks of the theoretical and experimental PXRD patterns are almost the same, confirming that the high phase purity of the title CPs. Furthermore, for evaluating the thermal stability of 1–3, TGA tests were performed under nitrogen flow from 25 to 800 C (Fig. S7) and the PXRD patterns after thermogravimetric tests of CPs 1–3 have been measured (Fig. S8). As for 1, the weight loss of one lattice EtOH and two lattice DMA molecules is observed in the range of 30–250 C (obsd: 8.62% and calcd: 9.51%), and then its framework began to collapse beyond 350 C. The residual weight of 35.28% is assigned to ZnO (calcd. 13.06%) and carbon (calcd. 22.22%). For 2, the weight loss of 7.93 below 3
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Fig. 5. Coordination environment of the Cd(II) ion in 3. (symmetry codes: A: 0.5-x, 1-y, z; B: 1.5-x, -y, z; C: x, 1.5-y, 1.5-z. Hydrogen atoms and lattice molecules are omitted for clarity).
Fig. 3. Coordition environment of the Zn(II) ion in 2. (symmetry codes: A: 1þx, y, z; Hydrogen atoms and lattice molecules are omitted for clarity).
Fig. 6. (a) Packing view of the 2D layers of 3. (b)The 3D supramolecular framework of 3. (c) Topology of the 3D supramolecular framework in 3.
The structures of 1–3 were further confirmed by IR spectra. As shown in Fig. S1-Fig. S3, there are one wide stretching vibration peak at 33002500 nm (ν-OH) and one strong stretching vibration peak at 19001650 nm (ν-C– – O) from –COOH of H2TZMB. For 1–3, there are the strong peak at 1900-1650 nm (ν-C– – O). But one wide peak at 3300-2500 nm (ν-OH) disappears, which is due to the deprotonation of H2TZMB. Besides, there is wide stretching vibration peak at 3500-3200 nm in 1–3, which manifests the new substances have been synthesized. Fig. 4. (a) 1D chain structure of TZMB2 linked to Zn(II) along the c-axis of 2. (b) 1D chain structure of 4,40 -bipb linked to Zn(II) along the a-axis of 2. (c) The 3D framework of 2 along the b-axis. (d) Topology of the framework in 2.
3.3. Luminescence measurements
200 C is ascribed to the release of one lattice EtOH and two lattice DMA molecules. When the temperature reached 400 C, the network began to decompose. The residual weight of 27.94% is attributed to ZnO (calcd. 7.12%) and carbon (calcd. 20.82%). For 3, the weight loss of 6.1% (calcd: 6.4%) corresponds to one lattice EtOH and one lattice DMA molecule below 190 C. The framework of 3 is stable before 340 C. The residual weight of 37.98% is attributed to CdO (calcd. 13.43%), Cd (10.51%) and carbon (calcd. 14.04%).
Luminescence spectra of ligands and CPs have been tested in the solid state at ambient temperature. There are strong emission peaks at 430–470 nm (λex ¼ 285 nm) for H2TZMB, at 440 nm (λex ¼ 280 nm) for bim, at 450–470 nm for 4,40 -bipb (λex ¼ 300 nm), at 380 nm (λex ¼ 280 nm) for bbibp and at 405 nm (λex ¼ 290 nm) for 3 (Fig. 7). The emission bands may originate from the ligand-centered (LC) π* → π electronic transitions [36]. Compared to the free ligands of H2TZMB, bim and 4,40 -bipb, the main emission peaks of 1 and 2 appeared at 445 nm (λex ¼ 350 nm) and 450 nm (λex ¼ 275 nm), which reveal slight variations. 4
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Because of its d10 electron configuration, Zn(II)/Cd(II) ions are hardly to oxidize or reduce. The emissions of CPs are neither ligand-to-metal charge transfer (LMCT) nor metal-to-ligand charge transfer (MLCT), but could be attributed to intraligand (π* → π) or (π* → n) luminescence emission [37,38]. 3.3.1. Detecting of solvent small molecules The difference of the emission peaks of 1 and 2 (Figs. S9a–9b) can mainly be assigned to the different coordinated modes of H2TZMB ligand and auxiliary ligands. To further research luminescence identification ability of 1 and 2, some commonly used solvents molecules, including H2O, DMA, DMF, MeOH, DMSO, n-Butanol, 1,4-dioxane, cyclohexanol, CH3CN, Nmethyl kelopyrrolidide (NMP) and acetone were selected as the analytes. The ground crystal powder of 1 and 2 (2 mg) was dispersed in different 2 mL above-mentioned solvents. The suspensions of analytes were placed in the dark for overnight to test the luminescence spectra. As depicted in Fig. S10, the luminescent intensity of 1@DMA suspensions showed the strongest, while the emission of 1@acetone suspensions exhibited the weakest at 375 nm (λex ¼ 310 nm). However, the luminescent intensity of 2@H2O suspensions revealed the strongest and the emission in acetone is similar to that of 1 at 440 nm (λex ¼ 365 nm) (Fig. S11). The change in luminescentintensities of 1 and 2 depends largely on the nature of the solvent. Especially, acetone has the most
Fig. 7. Photoluminescence of Nitrogen-based ligands, CPs 1–3 at ambient temperature in the solid state.
Fig. 8. The luminescence spectra and intensities for 1 at 375 nm (λex ¼ 310 nm) and 2 at 440 nm (λex ¼ 365 nm)) in aqueous solution with various inorganic cations (a and b for 1, c and d for 2). 5
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experiments were also measured. The luminescence intensity of 1 at 375 nm was increasingly quenched with the increasing of Fe3þ concentration from 0.01 mM to 0.7 mM (Fig. 9a). And the luminescence intensity of 2 at 440 nm was decreased gradually with the Fe3þ concentration change of 0.01 mM–0.545 mM (Fig. 9c). Here, the SternVolmer (S–V) model was used to calculate the relevant coefficients by the equation of I0/I ¼ 1 þ KSV [M], in which I0 and I are the luminescence intensities without and with adding the analytes, respectively, [M] is the concentrations of the analytes, and Ksv is quenching constant [41]. As shown in Fig. 7b and d, the S–V plots show good linear fittings (R2 ¼ 0.992 for 1, R2 ¼ 0.989 for 2) in the lower concentration range, which might be attributed to static quenching processes. Subsequently, as the concentration of Fe3þ increased, the S–V plots deviate from linearity and well accord with nonlinear Stern–Volmer, which may be ascribed to dynamic quenching processes. In brief, this phenomenon could be due to a combination of static and dynamic quenching [42]. The KSV values of Fe3þ are 4.193 103 for 1 and 1.172 104 for 2, respectively. The lower limit detection (LOD) of Fe3þ was obtained from 3δ/Ksv (δ: standard error) to be 7.15 104 for 1 and 2.56 104 for 2 [43]. Different luminescence quenching of cations to 1 and 2 may be caused by the difference in coordination patterns. 2 possesses two uncoordinated
remarkable quenching effect towards the luminescence of 1 and 2. This phenomenon is ascribed to Lewis-type acid-base interactions between the framework of CPs and acetone [39,40]. As shown in Figs. S12–S13, the PXRD results display that the original framework of 1 and 2 are still well retained in all tested solvents. Considering that water is closely related to people's survival, it is necessary to monitor the quality of water at all times. Therefore, 1 and 2 were dispersed in H2O (1@H2O and 2@H2O) as a normal solution in the following luminescent measurements. 3.3.2. Selective detecting of cations The above experimental results inspire us to further investigate the abilities of 1 and 2 for detecting common metal ions. The experimental procedures in tested solvents were performed to assess the detecting response towards cations by adding M(NO3)n aqueous solution (0.01 mmol L1, Mnþ ¼ Ca2þ, Cr3þ, Al3þ, Cd2þ, Co2þ, Ba2þ, Kþ, Cu2þ, Zn2þ, Naþ, Pb2þ, Agþ, Fe3þ) (Fig. 8a–b for 1, Fig. 8c–d for 2). Distinctly, most of metal cations have slight or moderate quenching effect, while Fe3þ ions present almost complete luminescent quenching to 1 and 2. The testing results suggest that 1 and 2 have high selectivity for the detection of Fe3þ ions. In addition, to evaluate the sensitivity of 1 and 2 for the detection of Fe3þ ions, quantitative luminescence titration
Fig. 9. (a) Emission spectra of 1 in H2O (λex ¼ 310 nm) with incremental addition Fe3þ ions. (b) The Stern-Volmer plot of I0/I versus Fe3þ of 1. (c) Emission spectra of 1 in H2O (λex ¼ 365 nm) with incremental addition Fe3þ ions. (d)The linear relationship of the SV plots of I0/I versus Fe3þ of 2. 6
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oxygen atoms of TZMB2 ligand as open Lewis base sites, which could bring about better luminescence quenching. The detection limit of 1 and 2 are lower than some reported CPs for detecting Fe3þ [44]. In order to study the anti-interference ability of CPs for other metal ions, the anti-interference experiments of 1 and 2 were carried out (Fig. S14-Fig. S15). The results showed that the luminescence quenching induced by Fe3þ ions is hardly influenced by the other metal ions. CPs 1 and 2 can effectively detect Fe3þ even in the presence of other metal ions. Moreover, recyclability was also studied, because the regenerative performance is very crucial for a luminescence sensor. Satisfyingly, the luminescence intensities of 1 and 2 are readily recovered by centrifuging and washing several times with deionized water (Fig. S16-Fig. S17). The luminescence intensities of CPs 1 and 2 are slightly lower than the original ones for five cycles. All the results reveal that 1 and 2 could be used as a probe for detecting Fe3þ ions with high recyclability, sensitivity and strong anti-interference ability. In order to investigate the luminescence quenching mechanisms of Fe3þ to CPs 1 and 2, some related research was carried out. Firstly, the PXRD patterns of 1 and 2 after luminescence experiments (Fig. S18, Fig. S19) are in accord with those of the theoretical ones, which indicates that the luminescence quenching is not caused by the collapse of CPs’ framework. Secondly, the UV–vis spectra of the analytes in water. (Fig. S20) shows that most of cations present absorption spectra in the range of 200–320 nm, but for Fe3þ ions, there is a relatively wide absorption band between 300 and 450 nm, which overlaps with the emission peak at 375 nm (1) and the emission peak at 440 nm (2), which shows that the inner filter effect plays a major role in luminescence quenching [45]. Furthermore, Lewis-type acid-base interaction between the Fe3þ ions as Lewis acid sites and the uncoordinated O/N atoms as Lewis base sites also plays a small role in luminescence quenching. However, this kind of interaction is very weak, because the samples (Fe3þ@1, Fe3þ@2) after luminescent quenching experiments were washed with distilled water and centrifuged, their luminescent performance was almost recovered. 3.4. Gas adsorption properties Fig. 10. (a) N2 and H2 adsorption and desorption isotherms at 77 K of 3a. (b) CO2 and CH4 adsorption and desorption isotherms at 273 K and 298 K of 3a.
The porosity of 3 further inspires us to investigate the adsorption isotherms of CO2, CH4, N2 and H2 at distinct temperatures. The sample was dispersed in dichloromethane (CH2Cl2) and exchanged with fresh solvent every 8 h for three times, and filter cake was heated at 180 C for 600 min under the vacuum to get activated sample (3a, [Cd(TZMB)(bbibp)]n). The PXRD pattern and TG of 3a were tested to further confirm the structural stability of 3a (Fig. S21) [46]. The Langmuir surface area and the Brunauer-Emmett-Teller (BET) surface are 34.31 m2 g1 and 27.34 m2 g1 for 3, respectively. As depicted in Fig. 10a, 3a presents a typical type-I sorption isotherm for N2 and H2 at 77 K with the maximum uptake of 37.09 cm3 g1 (4.65 wt%) and 90.67 cm3 g1 (0.81 wt%) at 1 bar, respectively, which proves that 3 has a microporous structure. The hysteretic desorption indicates the strong interaction between guest N2/H2 and host frameworks [47]. Besides, the adsorption isotherms of 3a were further measured at higher temperatures under identical pressure. As illustrated in Fig. 10b, the maximum adsorption amounts of CH4 and CO2 are 18.77 (1.34 wt%) and 49.77 cm3 g1 (9.77 wt%) at 273 K, 10.79 cm3 g1 (0.66 wt%) and 43.59 cm3 g1 (7.83 wt%) at 298 K, respectively. The above results showed that 3 has a visibly selective capture of CO2 over CH4. Meanwhile, the uptakes of CO2 exceed those of the previously reported MOFs such as ZIF-79 and ZIF-100, etc under the same conditions [48,49], which can be partially explained by the magnitude of the adsorption heat obtained by the virial equation based on the sorption isotherms. The Qst values of CO2 and CH4 are 37.30 kJ mol1 and 30.77 kJ mol1 (Fig. S22), respectively. It is well known that the removal of CO2 from natural gas is pivotal on account of the pipeline corrosion caused by acidic CO2 [50]. Hence, the selectivities of 3a for CO2/CH4 at a typical ratio for land fill gas (CO2:CH4 ¼ 0.50:0.50) and natural gas
(CO2:CH4 ¼ 0.05:0.95) were estimated by the ideal adsorbed solution theory (IAST) [51] (Fig. S23). At 298 K and 1 bar, the values of the selectivity of CO2/CH4 are 4.78 for land fill gas and 1.39 for natural gas, respectively. The possible reasons of the adsorption amounts of 3a for CO2 over CH4 and N2 are as follows: Firstly, the kinetic diameter of CO2 (3.3 Å) is smaller than those of N2 (3.64 Å) and CH4 (3.8 Å), which makes it easily enter the pores of 3a [52]. Secondly, the quadrupole moment of CO2 (1.4 1039 C m2) is larger than those of CH4 (0 C m2) and N2 (4.7 1040 C m2) [53], which enhances the interaction between CO2 and the framework of 3a. Thirdly, the uncoordinated N atoms of the framework as Lewis base are easy to interact with CO2 as Lewis acid. 4. Conclusion In conclusion, three CPs based on a mixed-ligand strategy have been synthesized under the solvothermal methods using Zn(II)/Cd(II), H2TZMB and N-heterocyclic ligands. Luminescent experiments indicate 1 and 2 have high sensitivity and selective detection towards Fe3þ ions, which make them expected to be promising materials in detecting Fe3þ under different solution conditions. Gas adsorption behaviors show the adsorption amounts of 3a for CO2 advantage over those of CH4 and N2, which indicates 3 has potential application prospects in the capture of CO2 from land fill gas. Furthermore, the luminescent quenching mechanisms of 1 and 2 are mainly attributed to inner filter effect and Lewis acid-base interaction. 7
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Acknowledgments
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The authors gratefully acknowledge the financial support of this work by the Natural Science Foundation of China (Grant 21676258), the international Scientific and Technological Cooperation Projects of Shanxi Province (201803D421080) and the support of innovative research team of inorganic-organic hybrid functional materials in North University of China. Appendix A. Supplementary data Supplementary data to this article can be found online at https://do i.org/10.1016/j.jssc.2019.120916. References [1] R.J. Hill, D.L. Long, N.R. Champness, P.R. Hubberstey, M. Schr€ oder, Acc. Chem. Res. 38 (2005) 335–348. [2] JunCheng Jin, Jian Wu, YongXiang He, BaoHong Li, Jian Qiang Liu, Rajendra Prasad, Abhinav Kumar, Stuart R. Batten, CrystEngComm 19 (2017) 6464–6472. [3] Jiang Wang, Linglin g Gao, Jie Zhang, Li Zhao, Xiaoqing Wang, Xiaoyan Niu, Liming Fan, Tuoping Hu, CrystEngComm 19 (2019) 630–637. [4] Lizhen Liu, Zizhu Yao, Yingxiang Ye, Liangji Chen, Quanjie Lin, Yisi Yang, Zhangjing Zhang, Shengchang Xiang, Inorg. Chem. 57 (2018) 12961–12968. [5] L. Ma, C. Abney and, W. Lin, Chem. Soc. Rev. 38 (2009) 1248–1256. [6] C. Gogoi, S. Biswas, Dalton Trans. 47 (2018) 14696–14705. [7] A. Barba Bon, A.M. Costero, S. Gil, M. Parra, J. Soto, R. Martínez-Maneez, F. Sancen on, Chem. Commun. 48 (2012) 2012–2014. [8] Chengyang Yu, Xiaodong Sun, Lifei Zou, Guanghua Li, Lirong Zhang, Yunling Liu, Inorg. Chem. 58 (2019) 4026–4032. [9] D. Zhao, X.H. Liu, Y. Zhao, P. Wang, Y. Liu, M. Azam, S.I. Al-Resayes, Y. Lu, W.Y. Sun, J. Mater. Chem. 5 (2017) 15797–15807. [10] Q. Zhao, F. Li, C. Huang, Chem. Soc. Rev. 39 (2010) 3007–3030. [11] J. Hu, K. Wu, S. Dong, M. Zheng, Polyhedron 153 (2018) 261–267. [12] Y. Salinas, R. Martínez-Maneez, M.D. Marcos, F. Sancen on, A.M. Costero, M. Parra, S. Gil, Chem. Soc. Rev. 41 (2012) 1261–1296. [13] S.W. Thomas, G.D. Joly, T.M. Swager, Chem. Rev. 107 (2007) 1339–1386. [14] K. Ingkaninan, A. Hazekamp, C.M. de Best, H. Irth, U.R. Tjaden, R. van der Heijden, J. van der Greef, Verpoorte, J. Nat. Prod. 63 (2000) 803–806. [15] L. Bohd alkov a, P. Bohdalek, E. Břízova, P. Pacherova, A.A. Kuběna, Sci. Total Environ. 633 (2018) 857–874. [16] XiaoYu Guo, ZhenPeng Dong, Fei Zhao, ZhiLiang Liu, YanQin Wang, New J. Chem. 43 (2019) 2353–2361. [17] J. Hu, T. Cheng, S. Dong, C. Zhou, X. Huang, L. Zhang, Microporous Mesoporous Mater. 272 (2018) 177–183. [18] H. Song, L. Zhang, F. Yu, B.C. Ye, Y. Li, Electrochim. Acta 208 (2016) 10–16. [19] H. Xu, C.S. Cao, X.M. Kang, B. Zhao, Dalton Trans. 45 (2016) 18003–18017. [20] X. Cui, K. Chen, H. Xing, Q. Yang, R. Krishna, Z. Bao, H. Wu, W. Zhou, X. Dong, Science 353 (2016) 141–144. [21] Z. Bao, D. Xie, G. Chang, H. Wu, L. Li, W. Zhou, H. Wang, Z. Zhang, M.J. Zaworotko, Q. Ren, B. Chen, H. Xing, Q. Yang, J. Am. Chem. Soc. 140 (2018) 4596–4603. [22] (a) R.K. Pachauri, A. Reisinger, IPCC Fourth Assessment Report, Intergovernmental Panel on Climate Change, 2007; (b) M.Z. Jacobson, Energy Environ. Sci. 2 (2009) 148–173. [23] (a) C.S. Song, Catal. Today 115 (2006) 115 2–11532; (b) J.R. Li, Y.G. Ma, M.C. McCarthy, J. Sculley, J.M. Yu, H.K. Jeong, P.B. Balbuena, H.C. Zhou, Coord. Chem. Rev. 255 (2011) 1791–1823. [24] M.R. Hudson, W.L. Queen, J.A. Mason, D.W. Fickel, R.F. Lobo, C.M. Brown, J. Am. Chem. Soc. 134 (2012) 1970–1973. [25] G.P. Ji, Z.Z. Yang, H.Y. Zhang, Y.F. Zhao, B. Yu, Z.S. Ma, Chem., Int. Ed. 55 (2016) 9685–9689. [26] ChengPeng Li, Bo-Lan Liu, Lei Wang, Yue Liu, Jia-Yue Tian, Chun-Sen Liu, Miao Du, ACS Appl. Mater. Interfaces (9) (2017) 7202–7208. [27] ChengPeng Li, Hang Zhou, Si Wang, Hong Han Yuan, Su-Zhen Zhang, Miao Du, Chem. Commun. (53) (2017) 4767–4770.
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Three new coordination polymers based on an N-heterocyclic carboxylic acid: Structural diversity, luminescent properties and gas adsorption Jinfang Liang, Jinxia Liang, Lijun Zhai, Haonan Wu, Xiaoyan Niu, Jie Zhang *, Tuoping Hu **
A R T I C L E I N F O
A B S T R A C T
Keywords: N-Heterocyclic aromatic carboxylic acid Coordination polymers Luminescent quenching Gas adsorption Quenching mechanism
Based on a mixed-ligand strategy, three new coordination polymers (CPs), namely {[Zn2(TZMB)2(bim)]⋅2DMA⋅EtOH}n (1), {[Zn2(TZMB)2(4,40 -bibp)⋅2DMA⋅EtOH]}n (2), and {[Cd(TZMB)(bbibp)] DMA⋅EtOH}n (3), (bim ¼ benzimidazole, 4,40 -bipb ¼ 4,40 -bis(pyrid-4-ly)biphenyl, bbibp ¼ 4,40 -bis(benzoimidazo-1-ly)biphenyl, DMA ¼ N, N-dimethylacetamide), have been successfully synthesized by the reaction of 4,4'-(1H-1,2,4-triazol-1yl)methylenebis (benzonic acid) (H2TZMB) and Zn(II)/Cd(II) under the solvothermal methods. The structural analyses indicate that 1 displays 2-nodal (3,4)-c 3D framework with a {63}{65.8} topology, 2 exhibits a rare 1D þ 1D → 3D framework with the same topology as 1, and 3 is a 3D supramolecular framework obtained by π … π stacking interaction between the adjacent 2D layers with the topology of {65.8}. Furthermore, the luminescent experiments indicate that 1 and 2 exhibit high sensitivity and selective detection towards Fe3þ ions with the low detection limit of 7.15 104 M1 and 2.56 104 M1, respectively. Gas adsorption behaviors show the adsorption amounts of 3a for CO2 advantage over those of CH4 and N2. The selectivities of 3a for CO2/CH4 were estimated by the ideal adsorbed solution theory (IAST), which are 4.78 for land fill gas (CO2:CH4 ¼ 0.50:0.50) and 1.39 for natural gas (CO2:CH4 ¼ 0.05:0.95), respectively. Finally, the luminescent quenching mechanisms are also discussed in detail.
1. Introduction Coordination polymers (CPs) have always been the focus of researchers in the past few years, which possess diverse architectures and complicated topologies as well as were widely used in the fields of luminescent detecting [1,2], gas adsorption/separation [3,4], catalysis [5]. With the progress of human society and heavy industry, a mass of toxic organic small molecules and hazardous metal ions are being discharged into environment and have posed many negative effects on human's health. Iron ion is essential in the process of metabolism, such as the formation of hemoglobin, muscular and brain growth, and the building-up process of RNA and DNA [6–8]. Both deficiency and overload of iron can pose serious health disorders such as insomnia, weakened immunity and skin diseases [9,10]. Therefore, it is highly urgent to detect Fe3þ ions [11-13]. Continuous research and efforts to address these issues by utilizing the traditional means, for instance, mass spectrometry (MS) [14], atomic absorption spectrometry (AAS) [15], ion mobility spectrum [16], gas chromatography and cyclic voltammetry [17,18] are often unsatisfactory. Because these modern analysis and technology have some
unavoidable pitfalls, such as high cost, fussy preparation phase, complex procedure and long response time. Hence, it is necessary to explore an efficient, convenient, low-cost and recyclable approach to track contaminants quickly. Nevertheless, on account of their high selectivity and sensitivity, recyclability and visualization, CPs have been deemed as one of more potential luminescent detectors to detect pollutants. What's more, some CPs own large surface area, modifiable tunnel, which give them great application prospect in areas of gas adsorption, storage and separation [19–21]. [19–21]. As we all known, carbon dioxide (CO2), as a persistent increasing greenhouse gas, primarily comes from burning of more and more fossil fuels [22,23]. The greenhouse effect can give rise to abnormal climate change and sea level rises. Hence, it is quite significant to seek material for capturing CO2 in order to alleviate the greenhouse effect and improve the environment quality. Compared to other porous materials, such as zeolite materials [24], organic polymers [25], CPs have the advantages of high stability and porous structure, which make them become functional materials for capture and separation of CO2 [26–31]. Therefore, designing and synthesizing novel multifunctional materials to detect contaminants are imminent for sustainable development and
* Corresponding author. ** Corresponding author. E-mail addresses: [email protected] (J. Zhang), [email protected] (T. Hu). https://doi.org/10.1016/j.jssc.2019.120916 Received 30 June 2019; Received in revised form 16 August 2019; Accepted 16 August 2019 Available online 20 September 2019 0022-4596/© 2019 Elsevier Inc. All rights reserved.
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C68H64O11N8Zn2: C, 62.80; H, 4.96; N, 8.61. Found (%): C, 62.85; H, 4.45; N, 8.62. IR (KBr pellet, cm1): 3448 (vs), 2376 (w), 1626 (s), 1558 (s), 1365 (s), 1132 (m), 999 (m), 810 (m), 775 (m), 651 (w), 628 (w), 563 (w).
human health. Therefore, in this work, based on Y-shaped {4,4'-(1H-1,2,4-triazol-yl) methylenebis(benzonic acid)}(H2TZMB) and three different rigid Nheterocyclic ligands (bim ¼ benzimidazole, 4,40 -bipb ¼ 4,40 -bis(pyrid-4ly)biphenyl, bbibp ¼ 4,40 -bis(benzoimidazo-1-ly)biphenyl) (Scheme 1), three new CPs, namely, {[Zn2(TZMB)2(bim)]⋅2DMA⋅EtOH}n (1), {[Zn2(TZMB)2(4,40 -bipb)⋅2DMA⋅EtOH]}n (2) and {[Cd(TZMB)(bbibp)]⋅ DMA⋅EtOH}n (3) have been synthesized under the solvothermal methods. Furthermore, the luminescent properties of 1 and 2, and the gas adsorption behaviors of 3 were also investigated.
2.2.3. Synthesis of {[Cd(TZMB)(bbibp)]⋅DMA⋅EtOH}n (3) The mixed solvent of DMA/EtOH/H2O (4 mL, v/v/v ¼ 1:1:2) was added into the mixture of H2TZMB ligand (0.024 mmol, 7.8 mg), NaOH (0.01 mol/L, 4.8 mL). The above mixture was transferred into a stainless steel vessel (25 mL) containing Cd(NO3)2⋅4H2O (0.012 mmol, 3.7 mg) and bbibp (0.024 mmol, 9.3 mg), which was adjusted to pH ¼ 3 by adding dropwise HNO3 (0.005 mol L1) aqueous solution. The vessel was sealed and heated to 110 C for 3 days and naturally cooled to ambient temperature to get orange-yellow crystals. Yield: 70.23% (based on Cd). Anal. calcd (%) for C49H44N8O6Cd: C, 61.73; H, 4.65; N; 11.75. Found (%): C, 61.74; H, 4.63; N, 11.80. IR (KBr pellet, cm1): 3448 (vs), 2970 (w), 1593 (s), 1506 (s), 1398 (m), 1299 (m), 1134 (m), 1006 (m), 829 (m), 742 (w), 648 (w), 582 (w), 534 (w).
2. Experimental 2.1. Materials and methods All chemical reagents have been purchased commercially and used without further purification. IR spectra were tested by a FTIR-8400s spectrometer with KBr pellet from 500 to 4000 cm1. Powder X-ray diffraction (PXRD) was performed by a diffractometer (Rigaku D/Max2500 PC) with Mo-Kα radiation at room temperature in the range of 5–50 (2θ). The contents of C, N, and H were determined by Vario MACRO analyzer (EA). The UV–vis spectra were performed on a UV2300 analytical instrument. Luminescent spectra were tesed by a F-2700 spectrophotometer. Thermal stability of CPs was measured under a ZCTA instrument from 25 to 800 C under nitrogen flow. Gas adsorption behaviours were evaluated on an ASAP-2020 analyzer.
2.3. Single crystal X-ray crystallography All crystallographic data of CPs 1–3 were obtained on a Bruker Smart CCD diffractometer (Mo-Kα radiation, λ ¼ 0.71073 Å) at 170(1)/273(2)/ 293(3)K. The structures were solved through direct method by means of SHELXTL-2016 program by the full-matrix least-squares method on F2. Crystallographic data and refinement parameters for 1–3 were presented in Table S1, selected bond angles and lengths are shown in Table S2. CCDC: 1917486 (1), 1917487 (2) and 1917488 (3).
2.2. Syntheses of CPs
3. Results and discussion
2.2.1. Synthesis of {[Zn2((TZMB)2(bim)]⋅2DMA⋅EtOH}n (1) NaOH (0.01 mol/L, 0.8 mL) was added into the mixture of the H2TZMB ligand (0.004 mmol, 1.3 mg) and a mixed solvent of DMA/ EtOH/H2O (1 mL, v/v/v ¼ 2:1:1), and then the mixture was transferred into a glass tube containing bim (0.008 mmol, 0.9 mg) and Zn(NO3)2⋅6H2O (0.008 mmoL, 2.4 mg). The glass tube was sealed and heated at 110 C for 3000 min and then naturally cooled to ambient temperature to obtain colorless block crystals. Yield: 88.35% (based on Zn). Anal. calcd (%) for C51H51Zn2N10O11: C, 55.14; H, 4.63; N, 12.61. Found (%): C, 55.02; H, 4.49; N, 12.89. IR (KBr pellet, cm1): 3448 (vs), 2370 (w), 1616 (s), 1558 (s), 1419 (s), 1282 (s), 1122 (s), 995 (m), 842 (m), 756 (m), 649 (m).
3.1. Structural descriptions 3.1.1. {[Zn2(TZMB)2(bim)]⋅2DMA⋅EtOH}n (1) Complex 1 crystallizes in the monoclinic space group C2/m and exhibits a 3D framework. The asymmetric unit includes one Zn(II) ion, one TZMB2 ligand, one bim, one lattice EtOH molecule and two lattice DMA molecules (Fig. 1). The central Zn(II) ion is bonded to three O atoms (O1, O2 and O3A) of two TZMB2 ligands and two atoms (N3, N2B) of one TZMB2 ligand and one bim ligand, respectively. The H2TZMB linker is completely deprotonated and shows a μ3-(κ 1κ 1)-(κ1-κ 1)-(κ1-κ 0) (Scheme 2, Mode III) coordination mode. As displayed in Fig. 2a, every TZMB2 ligand connects two Zn(II) ions to from a {Zn(COO)2} unit, which is linked by bim ligand to build a quasiquadrilateral 2D layer network. Among them, bim ligand as a linker only plays the role of stabilizing the structure. The adjacent 2D layers further interlock to form the 3D framework of 1 (Fig. 2b). By topological analysis performed on TOPOS Software [32], the
2.2.2. Synthesis of {[Zn2(TZMB)2(4,40 -bipb)]⋅2DMA⋅EtOH}n (2) The synthesis process of 2 is the same as l except that bim ligand (0.008 mmol, 0.9 mg) was replaced by 4,40 -bipb ligand (0.008 mmol, 2.5 mg) and the reaction system was adjusted to pH ¼ 4 by dropwise adding HNO3 (0.005 mol L1) aqueous solution. Colorless block crystals of 2 were collected. Yield: 74.12% (based on Zn). Anal. calcd (%) for
Scheme 1. The H2TZMB and N-Heterocyclic ligands. 2
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Fig. 1. Coordination environment of the Zn(II) ion in 1. (symmetry codes: A: 0.5 þ x, 0.5-y, 1þz; B: 0.5 þ x, 0.5-y, z; C: x, 1-y, z. Hydrogen atoms and lattice molecules are omitted for clarity).
Scheme 2. Diverse coordition modes of H2TZMB in 1–3.
whole 3D framework can be simplified to a 2-fold interpenetrated (3,4)-c net with the topology of (63)(65.8) (Fig. 2c), when TZMB2 ligand and {Zn(COO)2} unit can be seemed as 3-c node and 4-c node, respectively. 3.1.2. {[Zn2(TZMB)2(4,40 -bipb)]⋅2DMA⋅EtOH}n (2) Complex 2 crystallizes in the monoclinic space group P2/C. Its repeating unit contains two Zn(II) ions, two TZMB2 linkers, one 4,40 bipb ligand, one lattice EtOH molecule and two lattice DMA molecules (Fig. 3). The central Zn(II) ion is surrounded by two O atoms of two identical TZMB2 ligands [Zn–O ¼ 1.916(8) Å], and two N (N2A, N5) atoms of one TZMB2 ligand [Zn1–N2A ¼ 2.017(8) Å] and one 4,40 bbipb ligand [Zn1–N5 ¼ 2.051(7) Å], respectively, which are similar to those reported for other Zn-CPs (Table S3) [33]. The H2TZMB ligand is completely deprotonatand presents a μ3-(κ 1κ 0)-(κ 1-κ0))-(κ 1-κ 0) (Mode I, Scheme 1) coordination mode. Each TZMB2 ligand connects with three Zn(II) ions to obtain a Y-shaped 1D chain [Zn3-(TZMB)]n, which interconnect each other further to develop a circulating like-hexagon structure (Fig. 4a). Zn(II) ions and TZMB2 ligands are connected with 4,40 -bibp ligands to build another infinite 1D chain [Zn2-(TZMB)-(4,40 -bibp)]n (Fig. 4b). Then, the above two 1D chains interconnect with together to build a 3D framework (Fig. 4c). Topologically, the framework of 2 shows a 2-nodal (3,4)-c 3D framework with the topology of (63)(65.8) (Fig. 4d). According to the above structure analyses, 2 belongs to the third category of one-fold 1D þ 1D → 3D stable framework [34].
Fig. 2. (a) View of the 2D symmetrical quadrilateral channel along the a axis of 1. (b) The two-fold interpenetrating 3D framework of 1. (c) Topology of the 3D network in 1.
obtain a 3D supramolecular network. The cavity volume of 3 is 1221.9Å3 out of the 4920.5Å3 per unit cell volume by PLATON, and the porosity is estimated to be 26.4%. Topologically, the overall 3D supramolecular framework can be regarded as a 2-fold interpenetrated 4-c 3D framework with the topology of (65.8) (Fig. 6c). 3.2. Phase purity, thermal stability and IR spectra analyses
3.1.3. {[Cd(TZMB)(bbibp)]⋅DMA⋅EtOH}n (3) Complex 3 crystallizes in the orthorhombic space group Pnna. As exhibited in Fig. 5, the repeating unit contains one Cd(II) ion, one TZMB2 ligand, one bbibp ligand, one lattice EtOH molecule and one lattice DMA molecules. The central Cd(II) ion is linked by two nitrogen atoms of bbibp ligand [Cd–N ¼ 2.241(2) Å] and four oxygen atoms of two indentical TZMB2 ligands [Cd–O ¼ 2.286(2) Å], presenting a quasitriangular bipyramid geometry. The bond lengths of Cd–O/N are in agreement with that of the previously reported Cd-CPs (Table S3) [35]. The H2TZMB ligands present μ2-(κ 1-κ 1)-(κ1-κ 1) (Mode II, Scheme 1) coordination mode and link Cd(II) ions to construct two identical 2D chains (Fig. 6a). As can be seen from Fig. 6b, the two adjacent 2D networks further catenate with each other through π … π interactions to
The powder X-ray diffraction (PXRD) has been performed at ambient temperature to prove the purity of 1–3, As displayed in Figs. S4–S6, the characteristic peaks of the theoretical and experimental PXRD patterns are almost the same, confirming that the high phase purity of the title CPs. Furthermore, for evaluating the thermal stability of 1–3, TGA tests were performed under nitrogen flow from 25 to 800 C (Fig. S7) and the PXRD patterns after thermogravimetric tests of CPs 1–3 have been measured (Fig. S8). As for 1, the weight loss of one lattice EtOH and two lattice DMA molecules is observed in the range of 30–250 C (obsd: 8.62% and calcd: 9.51%), and then its framework began to collapse beyond 350 C. The residual weight of 35.28% is assigned to ZnO (calcd. 13.06%) and carbon (calcd. 22.22%). For 2, the weight loss of 7.93 below 3
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Fig. 5. Coordination environment of the Cd(II) ion in 3. (symmetry codes: A: 0.5-x, 1-y, z; B: 1.5-x, -y, z; C: x, 1.5-y, 1.5-z. Hydrogen atoms and lattice molecules are omitted for clarity).
Fig. 3. Coordition environment of the Zn(II) ion in 2. (symmetry codes: A: 1þx, y, z; Hydrogen atoms and lattice molecules are omitted for clarity).
Fig. 6. (a) Packing view of the 2D layers of 3. (b)The 3D supramolecular framework of 3. (c) Topology of the 3D supramolecular framework in 3.
The structures of 1–3 were further confirmed by IR spectra. As shown in Fig. S1-Fig. S3, there are one wide stretching vibration peak at 33002500 nm (ν-OH) and one strong stretching vibration peak at 19001650 nm (ν-C– – O) from –COOH of H2TZMB. For 1–3, there are the strong peak at 1900-1650 nm (ν-C– – O). But one wide peak at 3300-2500 nm (ν-OH) disappears, which is due to the deprotonation of H2TZMB. Besides, there is wide stretching vibration peak at 3500-3200 nm in 1–3, which manifests the new substances have been synthesized. Fig. 4. (a) 1D chain structure of TZMB2 linked to Zn(II) along the c-axis of 2. (b) 1D chain structure of 4,40 -bipb linked to Zn(II) along the a-axis of 2. (c) The 3D framework of 2 along the b-axis. (d) Topology of the framework in 2.
3.3. Luminescence measurements
200 C is ascribed to the release of one lattice EtOH and two lattice DMA molecules. When the temperature reached 400 C, the network began to decompose. The residual weight of 27.94% is attributed to ZnO (calcd. 7.12%) and carbon (calcd. 20.82%). For 3, the weight loss of 6.1% (calcd: 6.4%) corresponds to one lattice EtOH and one lattice DMA molecule below 190 C. The framework of 3 is stable before 340 C. The residual weight of 37.98% is attributed to CdO (calcd. 13.43%), Cd (10.51%) and carbon (calcd. 14.04%).
Luminescence spectra of ligands and CPs have been tested in the solid state at ambient temperature. There are strong emission peaks at 430–470 nm (λex ¼ 285 nm) for H2TZMB, at 440 nm (λex ¼ 280 nm) for bim, at 450–470 nm for 4,40 -bipb (λex ¼ 300 nm), at 380 nm (λex ¼ 280 nm) for bbibp and at 405 nm (λex ¼ 290 nm) for 3 (Fig. 7). The emission bands may originate from the ligand-centered (LC) π* → π electronic transitions [36]. Compared to the free ligands of H2TZMB, bim and 4,40 -bipb, the main emission peaks of 1 and 2 appeared at 445 nm (λex ¼ 350 nm) and 450 nm (λex ¼ 275 nm), which reveal slight variations. 4
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Because of its d10 electron configuration, Zn(II)/Cd(II) ions are hardly to oxidize or reduce. The emissions of CPs are neither ligand-to-metal charge transfer (LMCT) nor metal-to-ligand charge transfer (MLCT), but could be attributed to intraligand (π* → π) or (π* → n) luminescence emission [37,38]. 3.3.1. Detecting of solvent small molecules The difference of the emission peaks of 1 and 2 (Figs. S9a–9b) can mainly be assigned to the different coordinated modes of H2TZMB ligand and auxiliary ligands. To further research luminescence identification ability of 1 and 2, some commonly used solvents molecules, including H2O, DMA, DMF, MeOH, DMSO, n-Butanol, 1,4-dioxane, cyclohexanol, CH3CN, Nmethyl kelopyrrolidide (NMP) and acetone were selected as the analytes. The ground crystal powder of 1 and 2 (2 mg) was dispersed in different 2 mL above-mentioned solvents. The suspensions of analytes were placed in the dark for overnight to test the luminescence spectra. As depicted in Fig. S10, the luminescent intensity of 1@DMA suspensions showed the strongest, while the emission of 1@acetone suspensions exhibited the weakest at 375 nm (λex ¼ 310 nm). However, the luminescent intensity of 2@H2O suspensions revealed the strongest and the emission in acetone is similar to that of 1 at 440 nm (λex ¼ 365 nm) (Fig. S11). The change in luminescentintensities of 1 and 2 depends largely on the nature of the solvent. Especially, acetone has the most
Fig. 7. Photoluminescence of Nitrogen-based ligands, CPs 1–3 at ambient temperature in the solid state.
Fig. 8. The luminescence spectra and intensities for 1 at 375 nm (λex ¼ 310 nm) and 2 at 440 nm (λex ¼ 365 nm)) in aqueous solution with various inorganic cations (a and b for 1, c and d for 2). 5
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experiments were also measured. The luminescence intensity of 1 at 375 nm was increasingly quenched with the increasing of Fe3þ concentration from 0.01 mM to 0.7 mM (Fig. 9a). And the luminescence intensity of 2 at 440 nm was decreased gradually with the Fe3þ concentration change of 0.01 mM–0.545 mM (Fig. 9c). Here, the SternVolmer (S–V) model was used to calculate the relevant coefficients by the equation of I0/I ¼ 1 þ KSV [M], in which I0 and I are the luminescence intensities without and with adding the analytes, respectively, [M] is the concentrations of the analytes, and Ksv is quenching constant [41]. As shown in Fig. 7b and d, the S–V plots show good linear fittings (R2 ¼ 0.992 for 1, R2 ¼ 0.989 for 2) in the lower concentration range, which might be attributed to static quenching processes. Subsequently, as the concentration of Fe3þ increased, the S–V plots deviate from linearity and well accord with nonlinear Stern–Volmer, which may be ascribed to dynamic quenching processes. In brief, this phenomenon could be due to a combination of static and dynamic quenching [42]. The KSV values of Fe3þ are 4.193 103 for 1 and 1.172 104 for 2, respectively. The lower limit detection (LOD) of Fe3þ was obtained from 3δ/Ksv (δ: standard error) to be 7.15 104 for 1 and 2.56 104 for 2 [43]. Different luminescence quenching of cations to 1 and 2 may be caused by the difference in coordination patterns. 2 possesses two uncoordinated
remarkable quenching effect towards the luminescence of 1 and 2. This phenomenon is ascribed to Lewis-type acid-base interactions between the framework of CPs and acetone [39,40]. As shown in Figs. S12–S13, the PXRD results display that the original framework of 1 and 2 are still well retained in all tested solvents. Considering that water is closely related to people's survival, it is necessary to monitor the quality of water at all times. Therefore, 1 and 2 were dispersed in H2O (1@H2O and 2@H2O) as a normal solution in the following luminescent measurements. 3.3.2. Selective detecting of cations The above experimental results inspire us to further investigate the abilities of 1 and 2 for detecting common metal ions. The experimental procedures in tested solvents were performed to assess the detecting response towards cations by adding M(NO3)n aqueous solution (0.01 mmol L1, Mnþ ¼ Ca2þ, Cr3þ, Al3þ, Cd2þ, Co2þ, Ba2þ, Kþ, Cu2þ, Zn2þ, Naþ, Pb2þ, Agþ, Fe3þ) (Fig. 8a–b for 1, Fig. 8c–d for 2). Distinctly, most of metal cations have slight or moderate quenching effect, while Fe3þ ions present almost complete luminescent quenching to 1 and 2. The testing results suggest that 1 and 2 have high selectivity for the detection of Fe3þ ions. In addition, to evaluate the sensitivity of 1 and 2 for the detection of Fe3þ ions, quantitative luminescence titration
Fig. 9. (a) Emission spectra of 1 in H2O (λex ¼ 310 nm) with incremental addition Fe3þ ions. (b) The Stern-Volmer plot of I0/I versus Fe3þ of 1. (c) Emission spectra of 1 in H2O (λex ¼ 365 nm) with incremental addition Fe3þ ions. (d)The linear relationship of the SV plots of I0/I versus Fe3þ of 2. 6
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oxygen atoms of TZMB2 ligand as open Lewis base sites, which could bring about better luminescence quenching. The detection limit of 1 and 2 are lower than some reported CPs for detecting Fe3þ [44]. In order to study the anti-interference ability of CPs for other metal ions, the anti-interference experiments of 1 and 2 were carried out (Fig. S14-Fig. S15). The results showed that the luminescence quenching induced by Fe3þ ions is hardly influenced by the other metal ions. CPs 1 and 2 can effectively detect Fe3þ even in the presence of other metal ions. Moreover, recyclability was also studied, because the regenerative performance is very crucial for a luminescence sensor. Satisfyingly, the luminescence intensities of 1 and 2 are readily recovered by centrifuging and washing several times with deionized water (Fig. S16-Fig. S17). The luminescence intensities of CPs 1 and 2 are slightly lower than the original ones for five cycles. All the results reveal that 1 and 2 could be used as a probe for detecting Fe3þ ions with high recyclability, sensitivity and strong anti-interference ability. In order to investigate the luminescence quenching mechanisms of Fe3þ to CPs 1 and 2, some related research was carried out. Firstly, the PXRD patterns of 1 and 2 after luminescence experiments (Fig. S18, Fig. S19) are in accord with those of the theoretical ones, which indicates that the luminescence quenching is not caused by the collapse of CPs’ framework. Secondly, the UV–vis spectra of the analytes in water. (Fig. S20) shows that most of cations present absorption spectra in the range of 200–320 nm, but for Fe3þ ions, there is a relatively wide absorption band between 300 and 450 nm, which overlaps with the emission peak at 375 nm (1) and the emission peak at 440 nm (2), which shows that the inner filter effect plays a major role in luminescence quenching [45]. Furthermore, Lewis-type acid-base interaction between the Fe3þ ions as Lewis acid sites and the uncoordinated O/N atoms as Lewis base sites also plays a small role in luminescence quenching. However, this kind of interaction is very weak, because the samples (Fe3þ@1, Fe3þ@2) after luminescent quenching experiments were washed with distilled water and centrifuged, their luminescent performance was almost recovered. 3.4. Gas adsorption properties Fig. 10. (a) N2 and H2 adsorption and desorption isotherms at 77 K of 3a. (b) CO2 and CH4 adsorption and desorption isotherms at 273 K and 298 K of 3a.
The porosity of 3 further inspires us to investigate the adsorption isotherms of CO2, CH4, N2 and H2 at distinct temperatures. The sample was dispersed in dichloromethane (CH2Cl2) and exchanged with fresh solvent every 8 h for three times, and filter cake was heated at 180 C for 600 min under the vacuum to get activated sample (3a, [Cd(TZMB)(bbibp)]n). The PXRD pattern and TG of 3a were tested to further confirm the structural stability of 3a (Fig. S21) [46]. The Langmuir surface area and the Brunauer-Emmett-Teller (BET) surface are 34.31 m2 g1 and 27.34 m2 g1 for 3, respectively. As depicted in Fig. 10a, 3a presents a typical type-I sorption isotherm for N2 and H2 at 77 K with the maximum uptake of 37.09 cm3 g1 (4.65 wt%) and 90.67 cm3 g1 (0.81 wt%) at 1 bar, respectively, which proves that 3 has a microporous structure. The hysteretic desorption indicates the strong interaction between guest N2/H2 and host frameworks [47]. Besides, the adsorption isotherms of 3a were further measured at higher temperatures under identical pressure. As illustrated in Fig. 10b, the maximum adsorption amounts of CH4 and CO2 are 18.77 (1.34 wt%) and 49.77 cm3 g1 (9.77 wt%) at 273 K, 10.79 cm3 g1 (0.66 wt%) and 43.59 cm3 g1 (7.83 wt%) at 298 K, respectively. The above results showed that 3 has a visibly selective capture of CO2 over CH4. Meanwhile, the uptakes of CO2 exceed those of the previously reported MOFs such as ZIF-79 and ZIF-100, etc under the same conditions [48,49], which can be partially explained by the magnitude of the adsorption heat obtained by the virial equation based on the sorption isotherms. The Qst values of CO2 and CH4 are 37.30 kJ mol1 and 30.77 kJ mol1 (Fig. S22), respectively. It is well known that the removal of CO2 from natural gas is pivotal on account of the pipeline corrosion caused by acidic CO2 [50]. Hence, the selectivities of 3a for CO2/CH4 at a typical ratio for land fill gas (CO2:CH4 ¼ 0.50:0.50) and natural gas
(CO2:CH4 ¼ 0.05:0.95) were estimated by the ideal adsorbed solution theory (IAST) [51] (Fig. S23). At 298 K and 1 bar, the values of the selectivity of CO2/CH4 are 4.78 for land fill gas and 1.39 for natural gas, respectively. The possible reasons of the adsorption amounts of 3a for CO2 over CH4 and N2 are as follows: Firstly, the kinetic diameter of CO2 (3.3 Å) is smaller than those of N2 (3.64 Å) and CH4 (3.8 Å), which makes it easily enter the pores of 3a [52]. Secondly, the quadrupole moment of CO2 (1.4 1039 C m2) is larger than those of CH4 (0 C m2) and N2 (4.7 1040 C m2) [53], which enhances the interaction between CO2 and the framework of 3a. Thirdly, the uncoordinated N atoms of the framework as Lewis base are easy to interact with CO2 as Lewis acid. 4. Conclusion In conclusion, three CPs based on a mixed-ligand strategy have been synthesized under the solvothermal methods using Zn(II)/Cd(II), H2TZMB and N-heterocyclic ligands. Luminescent experiments indicate 1 and 2 have high sensitivity and selective detection towards Fe3þ ions, which make them expected to be promising materials in detecting Fe3þ under different solution conditions. Gas adsorption behaviors show the adsorption amounts of 3a for CO2 advantage over those of CH4 and N2, which indicates 3 has potential application prospects in the capture of CO2 from land fill gas. Furthermore, the luminescent quenching mechanisms of 1 and 2 are mainly attributed to inner filter effect and Lewis acid-base interaction. 7
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Acknowledgments
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