A Fluorescent Anionic MOF with Zn 4 (trz) 2 Chain for Highly Selective Visual Sensing of Contaminants: Cr(III) Ion and TNP
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1 Supporting Information for A Fluorescent Anionic MOF with 4 (trz) 2 Chain for Highly Selective Visual Sensing of Contaminants: Cr(III) Ion and TNP Xiao-Xia Jia, Ru-Xin Yao*, Fu-Qiang Zhang and Xian-Ming Zhang* School of Chemistry & Material Science, Shanxi Normal University, Linfen , Shanxi China. Table of Content Section 1. Experimental section Section 2. IR spectrum, TGA/DTA plots, PXRD patterns of 1 and atn net. Section 3. Heavy metal ions detection Section 4. Nitroaromatic sensing Section 5. Computational part Section 6. Supporting feferences Section 1. Experimental section Materials and physical measurements: All of the chemicals are commercially available and used without further purification. Elemental analyses of C, H and N were performed with a Vario EL-II elemental analyzer. The thermogravimetric analyses (TGA) were carried out under air atmosphere at a heating rate of 10 C/min using SETARAM LABSYS equipment. The FTIR spectra were obtained as KBr discs on a Nicolet 5DX spectrometer in the range cm-1. Powder X-ray diffraction (PXRD) data were collected in a Bruker D8 ADVANCE diffractometer (CuKα, λ= Å). The photoluminescence measurement was recorded on a FLS920 fluorescence spectrophotometer equipped with a continuous Xe-900 xenon lamp and a S1
2 µf900 microsecond flash lamp. UV-vis spectrum was monitored with a U-3310 spectrophotometer. Energy-disperse X-ray spectroscopy analysis (EDS) were measured on a JSM-7500F equipped with an EDAX CDU leap detector. Inductively Coupled Plasma (ICP) analysis was performed on a PE OPTIMA 8000DV optical emission spectrometer. X-Ray crystallography. The crystallographic data for 1 was collected on Agilent Technologies Gemini Eos diffractometer at K using Mo K α radiation (λ = Å). The program SAINT was used for integration of the diffraction profiles, and the program SADABS was used for absorption correction. The structures were solved by direct methods, and were refined anisotropically by full-matrix least-squares technique based on F 2 using the Olex2 programs. All non-hydrogen atoms were refined with anisotropic thermal parameters. H-atoms were refined isotropically with fixed thermal factors. Table S1. Selected bond length and bond angle for 1. 1 (1)-O(1) 1.978(5) (1)-O(5e) 1.928(5) (1)-N(3) 2.041(5) (1)-N(2) (5) (2)-N(4) 2.021(7) (2)-O(4d) 1.967(5) (2)-O(4e) 1.967(5) (2)-N(5) 2.030(7) (3)-O(11a) 1.957(5) (3)-O(7) 1.946(4) (3)-N(7) 2.033(4) (3)-N(6) 2.042(4) (4)-O(9b) 1.987(4) (4)-O(9) 1.986(4) (4)-N(8) 2.014(6) (4)-N(1c) 2.028(7) O(5d)-(1)-O(1) 106.7(3) O(1)-(1)-N(3) 100.3(2) O(1)-(1)-N(2) 110.0(2) O(5d)-(1)-N(3) 109.0(3) O(5d)-(1)-N(2) 122.5(3) N(2)-(1)-N(3) (19) O(4e)-(2)-O(4d) 95.9(4) O(4e)-(2)-N(4) 114.0(2) O(4d)-(2)-N(4) 114.0(2) O(4e)-(2)-N(5) 104.4(2) O(4d)-(2)-N(5) 104.4(2) N(4)-(2)-N(5) (3) S2
3 O(11a)-(3)-N(6) 100.0(3) O(11a)-(3)-N(7) 108.2(2) O(7)-(3)-O(11a) 129.5(2) O(7)-(3)-N(6) 104.6(2) O(7)-(3)-N(7) (19) N(7)-(3)-N(6) (17) O(9)-(4)-O(9c) 100.9(3) O(9c)-(4)-N(8) (18) O(9)-(4)-N(8) (18) O(9)-(4)-N(1b) 106.6(2) O(9c)-(4)-N(1b) 106.6(2) N(8)-(4)-N(1b) 116.5(3) Symmetry codes: (a)+y,1-x,-z; (b)+x,+y,-1+z; (c) 1/2-y,1/2-x,+z; (d)+y,1-x,1-z; (e)-1/2+x,1/2-y,1-z Section 2. IR spectrum, TGA/DTA plots, PXRD patterns of 1 and atn net Wavenumbers / cm -1 Figure S1. IR spectrum of 1 Figure S2. The coordinated mode of qptc 4- ligand in 1 S3
4 TG / % TG DTA T T / o C Figure S3. TGA/DTA plots of 1. Figure S4. View of atn net, compared to other types 4-c nets with ladders SBUs. in 75 water ph=10 ph=8 ph=6 ph=4 ph=2 as-synthesized simulated θ / deg Figure S5. PXRD patterns of 1 immersed in different ph values aqueous solutions in 75 C water for 24 h. Section 3. Heavy metal ions detection S4
5 Figure S6. The photographs of 1 in 10 ml aqueous solutions containing 0.01 M metal ions (Cd 2+, Mg 2+, Cs +, Mn 2+, Al 3+, La 3+, Hg 2+, Cr 3+ ), respectively. La 3+ Al 3+ Cd 2+ Mg 2+ Cs + Mn 2+ Hg 2+ Cr 3+ as-synthesized simulated θ / deg Figure S7. The PXRD patterns of simulated 1 and immersed in different metal ions aqueous solutions. Intensity C N Cr O Cr Cr Intensity C N O Cd Cd (a) Energy / KeV (b) Energy / KeV S5
6 Intensity C N O Mg Intensity C N Hg O Hg Hg Hg (c) Energy / KeV (d) Energy / KeV Intensity C N Mn O Mn Mn Intensity C N O Cs Cs Cs (e) Energy / KeV (f) Energy / KeV Intensity C N O Al (g) Energy / KeV (h) Figure S8. EDS analyses of 1-M (M = Cr 3+, Cd 2+, Mg 2+, Hg 2+, Mn 2+, Cs +, Al 3+, La 3+ ). Figure S9. The ICP percentage of different metal ions encapsulated by 1 S6
7 Figure S10. ICP percentage of interference experiment using solutions containing mixtures of metal ions (Cr 3+, Cd 2+, Al 3+, La 3+ ; Cr 3+, Mn 2+, Mg 2+, Cs + ) Figure S11. (a) Fluorescence lifetime (b) Luminescence decay curve of 1 Intensity (a.u.) MOF Cd 2+ Mg 2+ Cs + Mn 2+ Al 3+ La 3+ Hg 2+ Cr Wavelength (nm) Figure S12. Emission spectra of 1 in various metal ions aqueous solutions S7
8 5 4 I 0 /I I 0 /I x x x x10-5 (a) (b) x x x10-4 The concentration of Cr 3+ Figure S13. (a) Fluorescence quenching by incremental addition of Cr 3+ (0.01 mol/l) aqueous solution to suspension of 1, (b) Stern Volmer plot for Cr 3+. (a) (b) (c) (d) Intensity (a.u.) Al 3+ 0 µl 40 µl 80 µl 100 µl 120 µl 160 µl 200 µl (e) (f) Wavelength (nm) S8
9 Intensity (a.u.) La 3+ 0 µl 40 µl 80 µl 100 µl 120 µl 160 µl 200 µl (g) Wavelength (nm) Figure S14. The emission spectra of 1 dispersed in H 2 O upon incremental addition of M n+ (0.01 mol/l) solutions. (M n+ = Cd 2+, Mg 2+, Cs +, Mn 2+, Hg 2+, Al 3+, La 3+ ). Intensity (a.u.) MOF in H 2 O in 10-2 M Cr 3+ in 10-3 M Cr 3+ in 10-4 M Cr 3+ in 10-5 M Cr 3+ in 10-6 M Cr Wavelength (nm) Figure S15. Luminescent spectra of 1 as a result of different concentrations of Cr 3+, showing detection limit of 1 µmol/l for Cr Cr 3+ Abs Wavelength / nm Figure S16. UV/Vis spectra of solid 1 and 1-Cr 3+ S9
10 Section 4. Nitroaromatic sensing Figure S17. XPS spectrum of Cr 3+ for 1-Cr 3+ Intensity (a.u.) DMF 1,4-dioxane n-hexane 2-propanol DMA n-butanol H 2 O MeOH EtOH CH 3 CN NB 2,4-DNT TNP Wavelength (nm) Figure S18. Emission spectra of 1 dispersed in different solvents. Intensity (a.u.) 0 µl 10 µl 20 µl 50 µl 100 µl F 0 /F F 0 /F x x x10-5 C (mol/l) (a) Wavelength (nm) (b) x x x10-5 C (mol/l) S10
11 (c) Intensity (a.u.) 0 µl 10 µl 20 µl 50 µl 100 µl Wavelength (nm) (d) F 0 /F x x x x x x10-5 F 0 /F C (mol/l) Figure S19. (a) The emission spectra and (b) Stern Volmer plot for 1 dispersed in DMF, by gradual addition of NB solution (1 mmol/l). (c) The emission spectra and (d) Stern Volmer plot for 1 dispersed in DMF, by adding 2,4-DNT solution (1 mmol/l). C (mol/l) Figure S20. The emission spectra of 1 dispersed in DMF upon addition of TNP (0.1 mmol/l) solution. Inset: change of fluorescence before and after added TNP. 12 F 0 /F F 0 /F x x x10-6 C (mol/l) x x x10-6 C (mol/l) Figure S21. Stern Volmer plot of 1 dispersed in DMF upon addition of TNP (1 mmol/l) solution. S11
12 Figure S22. Fluorescence decay profile of 1 in the presence and absence of TNP Abs MOF 1 MOF 1 + 2µL TNP MOF 1 + 4µL TNP MOF 1 + 6µL TNP MOF 1 + 8µL TNP Abs MOF 1 NB 2,4-DNT (a) Wavelength / (nm) (b) Wavelength / (nm) Figure S23. (a) UV-vis spectra change of 1 upon gradual addition of TNP with the appearance of new band at 350 nm, (b) UV-vis spectra of 1 in the presence of NB and 2,4-DNT. Figure S24. Spectral overlap plots between the absorption spectra of nitro compounds and the emission spectrum of 1. Section 5. Computational Part All results reported in this study were performed at the DFT level by using the Amsterdam density functional (ADF ) program package. 1 Full geometry S12
13 optimizations were carried out by using the PBE 2 functional together with the ZORA-optimized TZP all-electron basis sets, in the presence of the COSMO 3 solvent model (water, ε = 78.4). The ionic radii which actually define the cavity in the COSMO are 1.700, 1.350, Å for C, H, O respectively. The value of the numerical integration parameter was 5.5. For all of the open-shell complexes, the unrestricted DFT approach was used. The coordination ability of different metal ion with the carboxylate oxygen atoms was evaluated by binding energy of single [C 6 H 5 CO 2 ] - to overall six-coordinated chelated [M(O 2 CC 6 H 5 ) 3 ] n- via following formula: [M(O 2 CC 6 H 5 ) 3 ] n- = [M(O 2 CC 6 H 5 ) 2 ] (n-1)- + [C 6 H 5 CO 2 ] - All the binding energies were obtained by single-point calculation under gas phase of the previously optimized structures. Table S2. Computed bond energies (ev) based on model of [M(O 2 CC 6 H 5 ) 3 ] n- (M = Cr 3+, Al 3+, La 3+, Mg 2+, Mn 2+, Cd 2+ and Hg 2+ ) at the level of PBE/TZP level metal ion [M(O 2 CC 6 H 5 ) 3 ] [M(O 2 CC 6 H 5 ) 2 ] [C 6 H 5 CO 2 ] - E Cr Al La Mg Mn Cd Hg [M(O 2 CC 6 H 5 ) 3 ] n- = [M(O 2 CC 6 H 5 ) 2 ] (n-1)- + [C 6 H 5 CO 2 ] - Table S3. A comparison of the Stern-Volmer constant (K sv ) and medium used for TNP detection of MOFs reported to data. NO. MOF K sv S13 Medium Used 1 This work DMF [NH 2 Me 2 ] [(TPT)] DMF ethanol 4 3 [(L)(HCOO) H 2 O] n H 2 O 5 Ref.
14 4 [Cd(BPDC) 0.5 (L1)(NO 3 )] 3.4DMF DMF 6 5 Zr 6 O 4 (OH) 8 (H 2 O) 4 (TTNA) 8/ H 2 O 7 6 [Cd(5-BrIP)(TIB)] n H 2 O 8 7 {[(tcpb) 0.5 (bpeb) 0.5 ] [0.5(bpeb) 2H 2 O]} n DMF 9 8 {[Cd 4 (L) 2 (L 2 ) 3 (H 2 O) 2 ](8DMF)(8H 2 O)} n ethanol (TZBPDC)(µ 3 -OH)(H 2 O) CHCl [Cd(fdc)(bpee) 1.5 ] 3(H 2 O) ethanol 12 Section 5. References 1. (a) Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Towards an order-n DFT method. Theor. Chem. Acc. 1998, 99, (b) te Velde, G.; Bickelhaupt, F. M.; van Gisbergen, S. J. A.; Guerra, C. F.; Baerends, E. J.; Snijders, J. G.; Ziegler, T. Chemistry with ADF. J. Comput. Chem. 2001, 22, (c) ADF , SCM; Theoretical Chemistry; Vrije University: Amsterdam, The Netherlands, 2. Perdew, J. P.; Burke K.; Ernzerh M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1996, 77, Klamt, A.; Schuurmann, G. COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc., Perkin Trans. 1993, 2, Zhang, C.; Yan, Y.; Sun, L.; Liang, Z.; Li, J., Solvent-induced construction of two zinc metal-organic frameworks for highly selective detection of nitroaromatic explosives. CrystEngComm 2016, 18, Yang, Y.; Shen, K.; Lin, J.-z.; Zhou, Y.; Liu, Q.-y.; Hang, C.; Abdelhamid, H. N.; Zhang, Z.-q.; Chen, H., A -MOF constructed from electron-rich [small pi]-conjugated ligands with an interpenetrated graphene-like net as an efficient nitroaromatic sensor. RSC Adv. 2016, 6, Yang, L.; Li, X.; Qin, C.; Shao, K.-Z.; Su, Z.-M., A fluorescent sensor for highly selective sensing of nitro explosives and Hg(ii) ions based on a 3D porous layer metal-organic framework. CrystEngComm 2016, 18, S14
15 7. Wang, B.; Lv, X.-L.; Feng, D.; Xie, L.-H.; Zhang, J.; Li, M.; Xie, Y.; Li, J.-R.; Zhou, H.-C., Highly Stable Zr(IV)-Based Metal Organic Frameworks for the Detection and Removal of Antibiotics and Organic Explosives in Water. J. Am. Chem. Soc. 2016, 138, Rachuri, Y.; Parmar, B.; Bisht, K. K.; Suresh, E., Mixed ligand two dimensional Cd(ii)/Ni(ii) metal organic frameworks containing dicarboxylate and tripodal N-donor ligands: Cd(ii) MOF is an efficient luminescent sensor for detection of picric acid in aqueous media. Dalt. Trans. 2016, 45, Sanda, S.; Parshamoni, S.; Biswas, S.; Konar, S., Highly selective detection of palladium and picric acid by a luminescent MOF: a dual functional fluorescent sensor. Chem. Commun. 2015, 51, Pal, T. K.; Chatterjee, N.; Bharadwaj, P. K., Linker-Induced Structural Diversity and Photophysical Property of MOFs for Selective and Sensitive Detection of Nitroaromatics. Inorg. chem. 2016, 55, Hu, Y.; Ding, M.; Liu, X.-Q.; Sun, L.-B.; Jiang, H.-L., Rational synthesis of an exceptionally stable (ii) metal-organic framework for the highly selective and sensitive detection of picric acid. Chem. Commun. 2016, 52, Singh, D.; Nagaraja, C. M., Auxiliary Ligand-Assisted Structural Variation of Cd(II) Metal Organic Frameworks Showing 2D 3D Polycatenation and Interpenetration: Synthesis, Structure, Luminescence Properties, and Selective Sensing of Trinitrophenol. Cryst. Growth Des. 2015, 15, S15
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