High-performance adsorption and separation of anionic dyes in. water using a chemically stable graphene-like metal-organic.
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 High-performance adsorption and separation of anionic dyes in water using a chemically stable graphene-like metal-organic framework Jun-Jiao Li a, Chong-Chen Wang a,b, Hui-Fen Fu a, Jing-Rui Cui a, Peng Xu c, Jie Guo a, and Jian-Rong Li *d a Beijing Key Laboratory of Functional Materials for Building Structure and Environment Remediation, Beijing University of Civil Engineering and Architecture, Beijing, , China b Beijing Advanced Innovation Center for Future Urban Design, Beijing University of Civil Engineering and Architecture, Beijing, , China c CAS Key Laboratory of Standardization and Measurement for Nanotechnology, National Center for Nanoscience and Technology, Beijing, , P.R. China d Department of Chemistry and Chemical Engineering, College of Environmental and Energy Engineering, Beijing University of Technology, Beijing , China Fig. S1 Structural formulae of tib and H 2 adc. Corresponding author. Tel.: ; fax: address: chongchenwang@126.com jianrongli@bjut.edu.cn
2 Fig. S2 Structural formulae of the dye molecules used in the dye adsorption and separation experiment. Materials and Instruments All chemicals were commercially available reagent grade and used without further purification. CHN Elemental analyses were performed using an Elementar Vario EL-III instrument. FTIR spectra were recorded on Nicolet-6700 Fourier transform infrared spectrophotometer in the region ranging from 4000 to 400 cm -1. Powder X-ray diffraction (PXRD) patterns were recorded on a Dandonghaoyuan DX-2700B diffractometer with Cu-Kα radiation. Thermogravimetric analyses were performed from 70 to 800 o C in an air stream at a heating rate of 10 o C min -1 on a DTU-3c thermal analyzer using a-al 2 O 3 as a reference. X-ray photoelectron spectra (XPS) measurement was operated with Thermo ESCALAB 250XI. Synthesis of BUC-17 A mixture of H 2 adc (0.3 mmol, g), CoSO 4 7H 2 O (0.3 mmol, g) and tib (0.3 mmol, g) was sealed in a 25 ml Teflon-lined stainless steel Parr bomb containing deionized H 2 O (10 ml), heated at 140 o C for 72 h, and then cooled down to room temperature. Red block-like crystals of BUC-17 (yield: 79% based on CoSO 4 7H 2 O) were isolated and washed with deionized water and ethanol. Anal. Calcd. for BUC-17, C 30 H 48 N 12 O 24 Co 3 S 3 : C, 29.2%; N, 13.6%; H, 3.9%. Found: C,
3 29.3%; N, 13.6%; H, 4.1%. IR (KBr)/cm -1 : 3360, 3131, 1672, 1623, 1546, 1515, 1317, 1257, 1273, 1182, 1125, 1078, 1012, 974, 848, 817, 758, 663, 612, 449. It is worth that H 2 adc did not participate in the formation of BUC-17 in the final product. But we failed to synthesize BUC-17 without the addition of H 2 adc, implying H 2 adc might play a role of a catalyst and ph regular. X-ray crystallography X-ray single-crystal data collection for BUC-17 was performed with Bruker CCD area detector diffractometer with a graphite-monochromatized MoKa radiation (λ = Å) using φ-ω mode at 298(2) K. The SMART software 1 was used for data collection and the SAINT software 2 for data extraction. Empirical absorption corrections were performed with the SADABS program 3. The structure has been solved by direct methods(shelxs-97) 4 and refined by full-matrix-least squares techniques on F 2 with anisotropic thermal parameters for all of the non-hydrogen atoms (SHELXL-97) 4. All hydrogen atoms were located by Fourier difference synthesis and geometrical analysis. These hydrogen atoms were allowed to ride on their respective parent atoms. All structural calculations were carried out using the SHELX-97 program package 4. Crystallographic data and structural refinement for BUC-17 are summarized in Table S1. Selected bond lengths and angles are listed in Table S2. Table S1 Details of X-ray data collection and refinement for BUC-17 Complex no. BUC-17 Formula C 30 H 48 N 12 O 24 Co 3 S 3 M Crystal system Rhombohedral Space group R3c a(å) (2) b(å) (2) c(å) (14) α( ) 90
4 β( ) 90 γ( ) 120 V(Å 3 ) (11) Z 6 μ(mo, Kα)(mm -1 ) Total reflections Unique 2432 F(000) 3798 Goodness-of-fit on F R int R ωr R 1 (all data) ωr 2 (all data) Largest diff. peak and hole(e/å 3 ) 0.392, Table S2. Selected bonds and angles for BUC-17 [Å and o ]. BUC-17 Bond lengths (Å) Co(1)-O(6) 2.068(3) Co(1)-O(5) 2.090(3) Co(1)-O(7) 2.108(3) Co(1)-O(8) 2.137(3) Co(1)-N(4) 2.151(4) Co(1)-N(2) 2.163(4) Bond angles ( o ) O(6)-Co(1)-O(5) 96.40(15) O(6)-Co(1)-O(7) 87.93(13) O(5)-Co(1)-O(7) (14) O(6)-Co(1)-O(8) (14) O(5)-Co(1)-O(8) 91.89(13) O(7)-Co(1)-O(8) 83.83(12) O(6)-Co(1)-N(4) 93.76(14) O(5)-Co(1)-N(4) 87.43(14) O(7)-Co(1)-N(4) 95.34(14) O(8)-Co(1)-N(4) 85.80(13) O(6)-Co(1)-N(2) 91.17(14) O(5)-Co(1)-N(2) 83.74(14) O(7)-Co(1)-N(2) 93.15(14) O(8)-Co(1)-N(2) 90.51(13) N(4)-Co(1)-N(2) (14) Table S3 Hydrogen bonds for BUC-17 (Å and o ) D-H d(d-h) d(h..a) <DHA d(d..a) A O5-H5C O4 [-y+1/3, -x+2/3, z+7/6] O5-H5D O8 [-x+y-1/3, -x+1/3, z+1/3] O6-H6C O1 [x, y, z+1 ] O6-H6D O3 [-x+y+1/3, -x+2/3, z+2/3] O6-H6D S1 [-x+y+1/3, -x+2/3, z+2/3] O7-H7C O1 [-x+y, y, z+1/2] O7-H7C S1 [-x+y, y, z+1/2] O7-H7D O4 [-x+y+1/3, -x+2/3, z+2/3]
5 O8-H8C O1 [x-1/3, x-y+1/3, z+5/6] O8-H8C S8 [x-1/3, x-y+1/3, z+5/6] O8-H8D O3 [-x+ y, y, z+1/2] O8-H8D S1 [-x+ y, y, z+1/2] Adsorption experiments To study the organic dye adsorption ability of BUC 17, four representative organic dyes with different charges, anionic Congo Red (CR) and Mordant Blue 13 (MB13), cationic Methylene Blue (MB), and neutral Sudan I (SI), were chosen in this work. A solid sample (50 mg) of the CPs with 0.08 mm particle size were added to 200 ml of CR (100 mg L -1 ), MB13 (20 mg L -1 ), MB (10 mg L -1 ) aqueous or SI (20 mg L -1 ) in ethanol solution in a 300 ml breaker, which were vibrated for a desired contact time in water bath shaker with speed of 150 r min -1 at 293 K. Sample of 5 ml aliquots were extracted and separated from the adsorbent by centrifugation (ZONKIA SC-3610) at 5000 rpm for 10 min. A Laspec Alpha-1860 spectrometer was used to monitor the CR, MB13, MB, SI concentration changes by the maximum absorbance at 493 nm, 551 nm, 672 nm and 480 nm, respectively. Separation experiments Dye adsorption in the mixture of different changes of dyes BUC-17 (10 mg) was added to 200 ml of dye-containing water solution with the initial concentration of CR (100 mg L -1 )/MB (20 mg L -1 ) and MB13 (20 mg L -1 )/MB (20 mg L -1 ). Then the mixtures were vibrated in constant temperature water of 25 o C bath shaker with speed of 150 r min -1. At a certain time interval, UV-Vis absorption spectra were recorded to determine the concentration of the dye solutions. Dye release
6 BUC-17 powder was immersed in CR dye solution and the dye loaded powders were collected and dried, thus obtaining Then 5.0 mg was placed in two cuvettes with 3.0 ml deionized water and 3.0 ml saturated Na 3 PO 4 solution, respectively. During the releasing process, the absorbance values of the CR in solution were recorded by UV-Vis spectrophotometry at different time interval until 12 h. Fig. S3 (a) Packing view of the framework assembled with the aid of H bonding interactions seen from a-axis for BUC-17. (b) Packing view of the framework of BUC-17 from c-axis. Fig. S4 UV-vis absorption spectra of CR (a) and MB13 (b) with BUC-17. Table S4 Comparison of the adsorption capacities of CR onto some typical adsorbents
7 Adsorption capacity Adsorbents (mg g -1 ) Ref. BUC This work Hypercrosslinked poly(styrene-co-divinylbenzene) resin [Ag 4 (dpe) 4 ] (butca) 13H 2 O MIL-100(Fe) {[Cu 3 (btb) 3 (nbta) 2 ] (H 2 O)} n complex CoFe 2 O HTMAB-modified attapulgite Coal-based mesoporous activated carbon Chitosan hydrobeads Magnetic (Fe 3 O 4 ) cellulose activated carbon Acid-activated bentonite Fig. S5 (a) Comparison of XRD patterns of the simulated one from single crystal data, BUC-17 before and after adsorption. (b) XPS wide scans spectra of BUC-17 before and after CR adsorption. Adsorption kinetic BUC-17 adsorbing CR was selected as the removal target to study the kinetic adsorption process. 10 mg BUC-17 was added into 200 ml of CR (150, 200, 250 mg L -1 ) solution at 293 K. All the mixtures were vibrated in constant temperature water bath shaker with speed of 150 r min ml sample was drawn at a certain time interval, immediately centrifuged to remove the particles as above. And the adsorption of dye was determined by Laspec Alpha-1860 spectrometer. Pseudo-first-model 15 and Pseudo-second-model 15 are widely used for the adsorption of an adsorbate from an aqueous solution. They can be expressed as linear form by Equations (1) and (2):
8 ln( q q ) ln( q ) k t e t e 1 (1) t q t 1 k q 2 2 e 1 t q e (2) where q t (mg g -1 ) and q e (mg g -1 ) is the amount of adsorbates adsorbed onto absorbents at t and at equilibrium time, respectively. k 1 (min 1 ) represents the adsorption rate constant which is calculated from the plot of ln (q e q t ) against t. k 2 (g mg -1 min -1 ) represents the pseudo-second-order rate constant of sorption. The plot of t/q t vs. t should exhibit a linear relationship, and the q e and k 2 can be obtained by the slope and intercept of the plot, respectively. Experimental Table S5. Parameters of kinetic model of CR with different concentration onto BUC-17 Pseudo-first-order Pseudo-second-order C 0 (mg L -1 ) k 1 (min -1 ) q e (mg g -1 ) R 2 k 2 (g mg -1 min -1 ) q e (mg g -1 ) R 2 value(mg g -1 ) Adsorption isotherms In addition, the bath adsorption was adopted to study the effect of temperature. 10 mg of BUC-17 was added to 200 ml CR aqueous solution with initial concentration of 150, 200, 250, 300, 350 mg L -1. The mixtures were agitated in constant temperature water bath shaker with speed of 150 r min -1 at different temperature (288, 293, 298, 303 and 308 K), respectively. When adsorption equilibrium was reached, the suspensions were centrifuged, and the concentrations of residual dye were also determined by Laspec Alpha-1860 spectrometer. The Langmuir, Freundlich, and Dubinin Radushevich (D-R) adsorption isotherm models were selected to describe equilibrium adsorption data of the CR and BUC-17. The Langmuir isotherm model expressed as Equation (3) 16 :
9 C / q 1/ ( K q ) C / q e e L max e max (3) Where, q max is the maximum amount of adsorption with complete monolayer coverage on the adsorbent surface (mg g -1 ). K L is the Langmuir constant related to the energy of adsorption which indicates the intensity of adsorption (L mg -1 ); high K L values mean strong bonding between the adsorbate and adsorbent. The K L and q max can be obtained from the linear plot of C e vs. C e /q e. The Freundlich isotherm model is listed in Equation (4) 17 : log q log K (1/ n) logc e f e (4) Where K f (mg g -1 ) and n are the Freundlich adsorption isotherm constants, being indicate of the extent of the adsorption and the degree of nonlinearity between solution concentration and adsorption, respectively. 1/n and logk f can be calculated from the slope and intercept of the linear plot between logc e and logq e, respectively. The D-R isotherm can be represented as Equation (5) 18 : 2 ln q ln q K e m DR (5) Where, K DR the activity coefficient related to mean sorption energy (mol 2 J -2 ), q m is the theoretical saturation capacity (mol g -1 ), ε represents the potential (J mol -1 ), which can be calculated using the equilibrium concentration C e (mg L -1 ) as Equation (6): RT ln( 1 1/ C e ) (6) K DR and q m can be obtained by the slope and intercept of the plot of lnq e vs ε 2, respectively. The mean free energy of adsorption (E, kj mol -1 ) can by expressed by Equation (7) E 2 1 K DR (7) Table S6. Constants of Langmuir, Freundlich, and D R for CR adsorption by BUC-17 at different
10 temperatures T/K Langmuir Freundlich D-R q max (mg g -1 ) K L (L mg -1 ) R 2 K f (L g -1 ) 1/n R 2 K DR E(KJ mol -1 ) R Thermodynamic parameters Standard free energy (ΔG 0, kj mol -1 ), change in enthalpy (ΔH 0, kj mol -1 ) and change in entropy (ΔS 0, J mol -1 K -1 ), were determined with the help of data obtained from Langmuir adsorption isotherm via Equations (8) and (9). 0 G RT ln K L S H ln K L R RT 0 0 (8) (9) Where R is the universal gas constant (8.314 kj mol -1 K -1 ) and T is the absolute temperature (K), K L is equilibrium constant, which depends on the temperature. ΔG 0 could be figured out by Equation 8. According to Equation 9, ΔS 0 and ΔH 0 parameters can be obtained from the slope and the intercept of the linear plot of lnk L vs.1/t, respectively. Table S7. Thermodynamic parameters for sorption process of CR on BUC-17 at different temperatures T/K K L (L mg -1 ) ΔG o (kj mol -1 ) ΔS o (J mol -1 K -1 ) ΔH o (kj mol -1 )
11 Fig. S6 Color changes of solutions containing (a) MB and (b) SI before (left) and after (right) addition of BUC-17 (2 h). Fig. S7 (a) UV-Vis spectral changes of the dye mixtures of MB13 and MB. (b)the picture of SPE setup, in which the original packing material C18 of SPE column was replaced by BUC-17. References S1. S. Bruker AXS, Version 5.611, Bruker AXS, Madison, WI, USA, S2. S. Bruker AXS, Version 6.28, Bruker AXS, Madison, WI, USA, S3. V. SADABS, Bruker AXS, Madison, WI, S4. S.-. G. M. Sheldrick, Göttingen University, Germany, S5. Y. Li, R. Cao, X. Wu, J. Huang, S. Deng and X. Lu, Journal of colloid and interface science, 2013, 400, S6. J. Zhang, C.-C. Wang, P. Wang and Y.-L. Cao, RSC Adv., 2016, 6, S7. S. E. Moradi, S. Dadfarnia, A. M. Haji Shabani and S. Emami, Desalination and Water Treatment, 2014, 56, S8. X.-X. Wang, Z.-X. Li, B. Yu, K. Van Hecke and G.-H. Cui, Inorganic Chemistry Communications, 2015, 54, S9. L. Wang, J. Li, Y. Wang, L. Zhao and Q. Jiang, Chemical Engineering Journal, 2012, , S10. H. Chen and J. Zhao, Adsorption, 2009, 15, S11. E. Lorencgrabowska and G. Gryglewicz, Dyes and Pigments, 2007, 74, S12. S. Chatterjee, S. Chatterjee, B. P. Chatterjee and A. K. Guha, Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2007, 299,
12 S13. M. Toor and B. Jin, Chemical Engineering Journal, 2012, 187, S14. S. Chatterjee, B. P. Chatterjee and A. K. Guha, Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2007, 299, S15. Y. S. Ho, Journal of Hazardous Materials, 2006, 37, S16. I. Langmuir, Journal of the American Chemical Society, 1916, 38, S17. H. Freundlich, The Journal of Chemical Physics, 1906, 57, 470. S18. D. A. N. S. M. Dubinin and L. Radushkevich, Ser. Khim, 1947.
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