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1 1 Supporting Information for Efficient and Selective Uptake of TcO 4 - by a Cationic Metal-Organic Framework Material with Open Ag + Sites DAOPENG SHENG,,, LIN ZHU,,, CHAO XU #, CHENGLIANG XIAO,, *, YANLONG WANG,, YAXING WANG,,, LANHUA CHEN,,, JUAN DIWU,,, JING CHEN #, ZHIFANG CHAI,, THOMAS E. ALBRECHT-SCHMITT, AND SHUAO,, * WANG School for Radiological and Interdisciplinary Sciences (RAD-X), Soochow University, , Suzhou, P. R. China Collaborative Innovation Center of Radiation Medicine of Jiangsu Higher Education Institutions, , Suzhou, P. R. China # Nuclear Chemistry and Chemical Engineering Division, Institute of Nuclear and New Energy Technology, Tsinghua University, Beijing , China Department of Chemistry and Biochemistry, Florida State University, 95 Chieftain Way, Tallahassee, Florida 32306, United States * Corresponding authors. xiaoc@suda.edu.cn (CHENGLIANG XIAO); shuaowang@suda.edu.cn (SHUAO WANG); Tel: ; Fax: Number of page: 17; These two authors contributed equally. Number of Figures: 17 (Figure S1 to Figure S17); Number of Tables: 7 (Tables S1 to Table S7); S1
2 Contents I. Experimental preparation for tipm and Tetrakis(4-bromophenyl)methane II. Exchange kinetics studies of inorganic materials III. The sorption data fitting by isotherm models IV. Single crystal structures and microscopic photograph of crystal V. PXRD and TGA data of SCU-100 VI. Characterization of sorption materials VII. - The sorption percentage of ReO 4 after irradiantion as compared with the original SCU-100 sample - VIII. Sorption isotherms and kinetics of ReO 4 by SCU-100, Mg-Al LDH, NDTB-1, Y 2 (OH) 5 Cl, and Yb 3 O(OH) 6 Cl IX. Characterization of sorption and desorption materials. X. Crystal data and structure refinements for complexes XI. Results of exchange efficiency of ReO - 4 by anion exchange sorbents XII. Competing ion exchange experiments XIII. Hydrogen bonds distances of SCU-100-Re. S2
3 I. Experimental preparation for tipm and Tetrakis(4-bromophenyl)methane Synthesis of Tetrakis(4-bromophenyl)methane 1 : Bromine (4.0 ml, 77.8 mmol) was added slowly to tetraphenylmethane (2.25 g, 7.02 mmol) with continuous stirring. The resulting slurry was stirred for an additional 5 h and then poured into ethanol (200 ml) which was cooled to -78. The precipitated solid was filtered, washed with saturated aqueous NaHSO 3 solution (80 ml 3) and dried at 50 under vacuum to give a yellow solid (4.45 g, 7.0 mmol) in 99.6% yield. 1 H NMR (DMSO-d, 400 MHz, 298 K, TMS) δ (ppm): (d, 8 H, benzene ring), (d, 8 H, benzene ring). Synthesis of the ligand tipm: The ligand tipm (tetrakis[4-(1-imidazolyl)phenyl]-methane) was synthesized according to a reported protocol with mild modifications. 2 A mixture of tetrakis(4-bromophenyl)methane (0.64 g, 1 mmol), imidazole (0.70 g, 10 mmol), K 2 CO 3 (0.83 g, 6 mmol), and CuI (0.08 g, 0.4 mmol) was finely ground and then heated under microwave irradiation (700 W) for 90 s. The resultant mixture was poured into water (10 ml), ethylenediaminetetraacetic acid (EDTA, 0.12 g, 0.4 mmol) and NH 3 H 2 O (25~28 %, 0.5 ml) were added, and then the mixture was stirred for 5 h. The solid product was collected by filtration, washed with water, and then purified by recrystallization from MeOH to afford yellow crystals, which were dried under vacuum to afford tipm as a light yellow solid (0.32 g ) in 50% yield. 1 H NMR (400 MHz, CDCl 3, 298 K, TMS): δ = 7.88 (s, 4 H, imidazole ring), 7.38 (s, 16 H, benzene ring), 7.29 (s, 4 H, imidazole ring), 7.22 (s, 4 H, imidazole ring) ppm. Tipm Crystals suitable for single crystal X-ray measurements were picked from the MeOH solution. Tipm ligand crystallizes in two different phase (Figure S1, Figure S2, and Table S1), which does not have an impact on the synthesis of SCU-100. II. Exchange kinetics studies of inorganic materials 50 mg of Mg-Al LDH, NDTB-1, Y 2 (OH) 5 Cl, and Yb 3 O(OH) 6 Cl sorbents were added into 50 ml of a solution containing 28 ppm TcO - 4 respectivily. The resulting mixture was stirred for a desired contact time by magnetic stirrer. UV-vis spectra were acquired to probe the concentration of TcO - 4 as a function of time using the absorption peak at 290 nm. In addition, 99 Tc concentration was also determined and confirmed by liquid scintillation counting (LSC). III. The sorption data fitting by isotherm models The Langmuir model assumes that the sorption of metal ions occurs on a homogenous surface by monolayer sorption and there no interaction between adsorbed ions, with homogeneous binding sites and equivalent sorption energies. The linear equation of the Langmuir isotherm S3
4 model is expressed as followed: 3 ce 1 ce = + (S1) q q k q e m L m where q m is the maximum sorption capacity corresponding to complete monolayer coverage (mg/g) and k L is a constant indirectly related to sorption capacity and energy of sorption (L/mg), which characterizes the affinity of the adsorbate with the adsorbent. The linearized plot was obtained when we plotted C e /q e against C e and q m and k L could be calculated from the slope and intercept. The Freundlich equation is an empirical equation based on sorption on a heterogeneous surface. The isotherm assumes that adsorbent surface sites have a spectrum of different binding energies. The linear equation can be expressed by: 1 ln qe = ln kf + ln c e (S2) n where k F and n are the Freundlich constants related to the sorption capacity and the sorption intensity, respectively. The linear plot was obtained by plotting lnq e against lnc e, and the values of k F and n were calculated from the slope and intercept of the straight line. Table S2 shows the fitting results using the Langmuir and Freundlich equations. In order to understand the sorption mode of ReO - 4 onto those cationic materials, the sorption data were applied to Langmuir and Freundlich. The sorption isotherm of NDTB-1 can be well fitted by the Langmuir model (Table S2, Figure S14), suggesting that monolayer and uniform sorption mode are more appropriate to explain the sorption mechanism of NDTB-1. Other three cationic materials are more fitted by the Freundlich model which exhibited different sorption mechanism with NDTB-1. S4
5 104 IV. Single crystal structures and microscopic photograph of crystal Figure S1. Microscopic photograph of SCU-100 crystals Figure S2. Crystal structure depictions of SCU-100: (a) one single network of [Ag 2 (tipm)] 2+ with large voids, (b) simplified topological structure of 8-fold interpenetration. Atom colors: Ag=red, N=green, C=light blue. In (b), different colors represent different single sets of the interpenetration. 115 S5
6 Figure S3. Overall 3D framework structure of SCU-100 with 1D channel Figure S4. (a) simplified topological structure of 8-fold interpenetration of SCU-100 and (b) topological structure of 4-fold interpenetration of SCU-100-Re. different colors represent different single sets of the interpenetration. S6
7 Figure S5. Crystal structure of (a) Yb 3 O(OH) 6 Cl, (c) NDTB-1,(d) Y 2 (OH) 5 Cl and molecular simulation model of (b) Mg-Al LDH. S7
8 128 V. PXRD and TGA data of SCU-100 Intensity (a.u.) As-synthesized Simulated θ (degree) Figure S6. PXRD patterns of SCU-100: simulated (blue) and as-synthesized (red). 110 Weight(%) ~3% Temperature ( o C) Figure S7. Thermogravimetric (TG) plot of SCU-100. S8
9 136 VI. Characterization of sorption materials Transmitance (a.u.) As-synthesized ReO 4 - exchanged 896 cm -1 ReO Wavenumber /cm -1 Figure S8. FT-IR spectra of SCU-100 as-synthesized and ReO 4 - loaded sample Figure S9. SEM images and EDS mapping profiles of ReO 4 - -loaded SCU-100 sample. S9
10 Intensity (a.u.) simulated SCU-100 simulated SCU-100-Re SCU-100-Re θ (degree) Figure S10. PXRD patterns of simulated SCU-100 (black), simulated SCU-100-Re (blue) and ReO - 4 sorbed SCU-100 (red). Intensity (a.u.) simulated SCU-100 SO SCU-100 PO SCU θ (degree) Figure S11. PXRD patterns of simulated SCU-100 (blue), SCU-100 crystals by soaking in the concentration of 0.1 M Na 2 SO 4 (red), and NaH 2 PO 4 solutions (olive). S10
11 VII. The sorption percentage of ReO 4 - after irradiantion as compared with the original SCU-100 sample 140 Removal Percentage (%) Figure S12. The sorption percentage of ReO 4 - after irradiantion as compared with the original SCU-100 sample. 157 Removal Percentage (%) Figure S13. The sorption percentage of ReO 4 - after immersed in aqueous solutions with different ph values ranging from 1 to S11
12 VIII. Sorption isotherms and kinetics of ReO 4 - Y 2 (OH) 5 Cl, and Yb 3 O(OH) 6 Cl by SCU-100, Mg-Al LDH, NDTB-1, q (mg ReO q (mg ReO 4 -/g sorbent) 4 -/g sorbent) LDHs Langmuir model Freundlich model Yb 3 O(OH) 6 Cl Langmuir model Freundlich model Ceq (mg/l) q (mg ReO 4 -/g sorbent) q (mg ReO 4 -/g sorbent) NDTB-1 Langmuir model Freundlich model Y 2 (OH) 5 Cl Langmuir model Freundlich model Ceq (mg/l) Ceq (mg/l) Ceq (mg/l) Figure S14. Sorption isotherms of ReO - 4 by Mg-Al LDH, NDTB-1, Y 2 (OH) 5 Cl, and Yb 3 O(OH) 6 Cl materials. solid line: Langmuir model; dotted line: Freundlich model. Removal Percentage (%) 140 SCU-100 NDTB Y 2 (OH) 5 Cl 120 Yb 3 O(OH) 6 Cl Mg- Al LDH Contact time (min) Figure S15. Comparison of the sorption kinetics of TcO - 4 by SCU-100, Mg-Al LDH, NDTB-1, Y 2 (OH) 5 Cl, and Yb 3 O(OH) 6 Cl materials. S12
13 173 IX. Characterization of sorption and desorption materials. Intensity (a.u.) ReO 4 - desorption ReO 4 - exchange As-synthesized Simulated θ (degree) Figure S16. PXRD patterns of simulated (black), as-synthesized (blue), ReO - 4 exchanged (red), and ReO - 4 desorption (olive) SCU-100. Transmitance (a.u.) a b c ReO Wavenumber /cm -1 Figure S17. FT-IR spectra of (a) the original (black), (b) ReO exchanged (red), and (c) ReO 4 desorption (blue) SCU-100. S13
14 X. Crystal data and structure refinements for complexes Table S1. Crystal data and structure refinements for complexes. SCU-100 SCU-100-ReO 4 - Empirical formula C 37 H 28 Ag 2 N 10 O 6 C 37 H 28 Ag 2 N 8 O 8 Re 2 Formula weight Crystal system Tetragonal Tetragonal Space group P4 2 /nbc P-4 a(å) (3) (11) b(å) (3) (11) c(å) (5) (7) α( ) β( ) γ( ) Volume(Å 3 ) 7759(3) (3) Z 8 2 ρcalcd (g cm - 3) µ(mm -1 ) F(000) R int Data collected Independent data Goodness-of-fit R a 1 (I>2σ(I)) wr b 2 (I>2σ(I)) a R 1 = Σ F o - F c /Σ F o. b wr 2 = Σw( F o 2 - F c 2 ) /Σ w(f o ) 2 1/2, where w = 1/[σ 2 (F o 2 ) + (ap) 2 + bp]. P= (F o 2 + 2F c 2 )/3. S14
15 XI. Results of exchange efficiency of ReO - 4 by anion exchange sorbents Table S2. Fitting results from the Langmuir and Freundlich fitting. Langmuir Freundlich Samples q m (mg g -1 ) K L (L mg -1 ) R 2 k F (L n /mol n-1 g) n R 2 Mg-Al-LDH NDTB Y 2 (OH) 5 Cl > 0.99 Yb 3 O(OH) 6 Cl Table S3. Results of studies on exchange efficiency of ReO - 4 by SCU-100, Mg-Al LDH, NDTB-1, Y 2 (OH) 5 Cl, Yb 3 O(OH) 6 Cl, Purolite A532E and A530E materials. - Intial concentration of Final percentage of ReO 4 Samples K d (ml/g) ReO - 4 (ppm) removed (%) Mg-Al- LDH 48 21% 262 NDTB % 652 Y 2 (OH) 5 Cl 48 10% 112 Yb 3 O(OH) 6 Cl 48 11% 120 SCU > 99% Purolite A532E 28 > 99% Purolite A530E 28 > 99% SCU > 99% S15
16 XII. Competing ion exchange experiments Table S4. Competing ion exchange experiments of ReO 4 - (0.15 mm) by SCU-100 in presence of different amounts of NO 3 -. n n ReO4- NO3- Removal sample n : n NO3- ReO4- K d (mm) (mm) (%) (ml/g) : SCU-100 5: : : : Table S5. ReO 4 - adsorption capacity of SCU-100 in the presence of different concentration of SO 4 2- as studied by ICP-OES (C ReO4- = M). Sample Mole ratio of n(reo 4 - ) : n(so 4 2- ) %ReO 4 - removal 1: % 1:1 99.6% SCU-100 1: % 1: % 1: % 1: % S16
17 Table S6. ReO 4 - adsorption capacity of SCU-100 in the presence of different anions as studied by ICP-OES (~0.5mM). Samples Solution ReO 4 - (ppm) PO 4 3- (ppm) SO 4 2- (ppm) %ReO 4 - removal %PO 4 3- removal %SO 4 2- removal ReO 4 - +PO 4 3- Stock After ion-exchange % 1.3% -- SCU-100 ReO 4 - +SO 4 2- Stock After ion-exchange % % ReO 4 - +CO 3 2- Stock After ion-exchange % ReO 4 - +PO 4 3- Stock A530E After ion-exchange ReO 4 - +SO 4 2- Stock % 34% After ion-exchange % % ReO 4 - +PO 4 3- Stock A532E After ion-exchange ReO 4 - +SO 4 2- Stock % 16% After ion-exchange % % S17
18 XIII. Hydrogen bonds distances of SCU-100-Re Table S7. Hydrogen bonds distances (Å) of compound SCU-100-Re. Bond type Distance(Å) Bond type Distance (Å) Re1-O1 H5 2.58(1) Å Re1-O3 H7A 2.75(7) Å Re1-O1 H (9) Å Re1-O3 H14A 2.71(6) Å Re1-O2 H5 2.76(5) Å Re1-O3 H17A 2.61(7) Å Re1-O2 H6A 2.59(9) Å Re1-O3 Ag1 2.74(6) Å Re1-O2 Ag1 2.81(1) Å Re1-O4 H6A 2.76(4) Å Re1-O4 H11A Re1-O4 H12A Re1-O4 H16A 2.56(0) Å 2.40(4) Å 2.88(3) Å References: (1) He, Y.; Xiang, S.; Chen, B. A microporous hydrogen-bonded organic framework for highly selective C 2 H 2 /C 2 H 4 separation at ambient temperature. J. Am. Chem. Soc. 2011, 133 (37), (2) Li, D. X.; Ren, Z. G.; Young, D. J.; Lang, J. P. Synthesis of two coordination polymer photocatalysts and significant enhancement of their catalytic photodegradation activity by doping with Co 2+ ions. Eur. J. Inorg. Chem. 2015, 2015 (11), (3) Langmuir, I. The adsorption of gases on plane surfaces of glass, mica and platinum. J. Am. Chem. Soc. 1918, 40 (9), S18
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