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1 Supporting Information Atom-Precise Modification of Silver(I) Thiolate Cluster by Shell Ligand Substitution: A New Approach to Generation of Cluster Functionality and Chirality Si Li, Xiang-Sha Du, Bing Li, Jia-Yin Wang, Guo-Ping Li, Guang-Gang Gao*, and Shuang-Quan Zang*, College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou , China School of Materials Science and Engineering, University of Jinan, Jinan , China zangsqzg@zzu.edu.cn; mse_gaogg@ujn.edu.cn. S1
2 Table of Contents Experimental section. S3 X-ray crystallography... S4 Photophysical measurements. S4 Supplementary Figures.. S5-S22 Tables of crystal data and structure refinements.. S23-S25 Supplementary References. S25 S2
3 Experimental Section Materials and Reagents. All chemicals and solvents obtained from suppliers were used without further purification. All solvents were analytical grade reagent. Instrumentation. 1 H NMR spectra were recorded on a Bruker DRX spectrometer operating at 400 MHz in CD 3 OD or CDCl 3. X-ray powder diffraction (PXRD) patterns of the samples were recorded on a D/MAX-3D diffractometer. Fourier transform infrared (FT-IR) spectra were recorded on a Bruker TENSOR 27 FT-IR spectrometer in the cm 1 region with KBr pellets. Transmission electron microscopy (TEM) images were obtained using a JEM-2100 electron microscope operated at 300 kv. TEM specimens were prepared by depositing one or two drops of the sample solutions onto carbon-coated copper grids. General procedures: Synthesis of complex 1. Complex 1 was synthesized by the reaction of 0.05 mmol [AgS t Bu] n precursor with 0.05 mmol AgNO 3 in 4 ml acetonitrile-dmac (v:v = 1:1) at room temperature. The mixture was treated under ultrasonic conditions until a clear solution was obtained. The resultant solution was allowed to evaporate slowly in darkness at room temperature for three days to give colorless block crystals. Yield: 60.3% (based on Ag). Elemental analysis calcd. (%) for C 57 H 126 N 12 S 10 Ag 20 O 31 ( ): C 17.32; H 3.21; N 4.25; S 8.11; found: C 17.43; H 3.22; N 4.27; S Synthesis of complexes 2-4. Benzoic acid (9 mg, 0.04 mmol) was added to the clear colorless solution of 1 under vigorous stirring at room temperature. And trimethylamine (20 μl) was added to the solution after benzoic acid was completely dissolved, the color of the clear solution changed from colorless to pale yellow within 10 min. The resultant solution was allowed to evaporate slowly in darkness at room temperature for two days to give colorless block crystals. Yield: 68.7% (based on Ag). The synthetic methods of complexes 3-4 are similar to 2 expect for the ligand was changed to alrestatin (6 mg, mmol) or ferrocenecarboxylic acid (14 mg, 0.042mmol). Yields: 36.4% (for 3) and 84.3% (for 4) based on Ag. Elemental analysis calcd. (%) for C 109 H 154 N 4 O 21 S 10 Ag 20 ( , 2): C 30.20; H 3.58; N 1.29; S 7.40; found: C 30.15; H 3.51; N 1.26; S For C 161 H 166 N 12 O 35 S 10 Ag 20 ( , 3): C 36.43; H 3.15; N 3.17; S 6.04; found: C 36.34; H 3.08; N 3.05; S For C 139 H 181 N 5 O 21 Fe 8 S 10 Ag 20 ( , 4): C 32.21; H 3.52; N 1.35; S 6.18; found: C 32.14; H 3.43; N 1.28; S Synthesis of complexes 5 and 7. A freshly prepared solution of L-alanine or D-alanine (2 mg, mmol in 40 μl of water) was added to the clear colorless solution of 1 under vigorous stirring at room temperature and followed by addition of triethylamine (50 μl), in which the clear colorless solution change muddy immediately. Then, extra silver nitrate (0.1 mmol) was added to the suspension solution and it turned into a clear colorless solution. The resultant solution was allowed to evaporate slowly in darkness at room temperature for two days to give colorless block crystals. Yields: 47.7% for 5a and 47.2% for 5b based on Ag. The synthetic method of complex 7 is similar to 5 expect for the ligand was change to L-proline or D-proline (12 mg, 0.1 mmol in 240 μl of water). Yields: 58.5% (7a) and 57.9% (7b) based on Ag. Elemental analysis calcd. (%) for C 114 H 242 N 24 S 20 Ag 44 O 59 ( , 5): C 16.53; H 2.94; N 4.06; S 7.74; found: C 16.44; H 2.89; N 4.02; S For C 89 H 174 N 16 S 10 Ag 24 O 35 ( , 7): C 21.65; H 3.55; N 4.54; S 6.49; found: C 21.55; H 3.46; N 4.41; S Synthesis of complex 6. A freshly prepared solution of L-valine or D-valine (4 mg, mmol in 160 μl of water) was added to the clear colorless solution of 1 under vigorous stirring at room temperature and followed by addition of triethylamine (50 μl), the clear colorless solution become muddy immediately. Then, extra silver nitrate (20 mg, mmol) and 2 ml toluene were added to the suspension. The suspension was then centrifuged for 5 min at r min -1. The supernatant was collected and was allowed to evaporate slowly in darkness at room temperature for two days to give colorless block crystals. Yields: 56.3% (6a) and 60.2% (6b) based on Ag. Elemental analysis calcd. (%) for C 73 H 154 N 11 S 10 Ag 23 O 28 ( ): C 19.77; H 3.50; N 3.47; S 7.23; found: C 19.82; H 3.43; N 3.55; S S3
4 In all of these compounds, complexes 2-4 are soluble in dichloromethane and chloroform; complexes 5 and 7 are soluble in ethanol and methanol, and complex 6 is soluble in acetonitrile and methanol. These results illustrate that ligand-substitution has an impact on the solubility of the resulting clusters. In general, aromatic protecting ligands are helpful for the compound to dissolve in the low polar solvent, and aliphatic ligands are favorable to dissolve in the high polar solvent, which provide convenience for subsequent testing in solutions. Synthesis of complexes 5, 6 and 7. Powders 5, 6 and 7 were precipitate from the same reaction solution of complexes 5, 6 and 7 aside from the addition of AgNO 3. These precipitates were washed several times using diethyl ether and deionized water, then colleceted by centrifugation, and dried in the air for subsequent testing. X-Ray Crystallography Single-crystal X-ray diffraction measurement of complexes 1-5b, 7a and 7b were performed on a Rigaku XtaLAB Pro diffractometer. Data collection and reduction were performed using the program CrysAlisPro. S1 Complexes 6a and 6b were performed on a Bruker D8 diffractometer. Data collection and reduction were performed using the program SADABS. S2 All the structures were solved with direct methods (SHELXS) S3 and refined by full-matrix least squares on F 2 using OLEX2, S4 which utilizes the SHELXL-2015 module. S5 All the atoms were refined anisotropically with the exception of some solvent molecules. Hydrogen atoms were placed in calculated positions refined using idealized geometries and assigned fixed isotropic displacement parameters. Intrinsic disorder occurred in all 10 structures, although all X-ray intensity data displayed reasonably good quality as reflected by their low R int ( ) and R sigma ( ) values. Structure refinement was handled with different strategies according to the electron density distribution and the complexity of the disorder. The imposed the restraints and constraints (ISOR, SIMU, DELU, SADI, DANG, etc.) in least-squares refinement of each structure were commented in the corresponding crystallographic CIF files. A satisfactory disorder model for the solvent molecules was not found in complexes 3, 5a, 5b, 6a and 6b, therefore the OLEX2 Solvent Mask routine (PLATON/SQUEEZE) S6 was used to mask out the disordered density. The detailed information of the crystal data, data collection and refinement results for all compounds are summarized in Tables S2-6. Photophysical Measurements UV-Vis absorption spectra were recorded using a Hitachi UH4150 UV-Visible spectrophotometer in the range nm. Solid-state emission and excitation spectra at different temperature were recorded with an Edinburgh FLS980 fluorescence spectrometer. The solid samples were loaded in a quartz tube inside a quartz-walled Dewar flask and liquid nitrogen was placed into the Dewar flask for low temperature glass photophysical measurements. Luminescence lifetime was measured on an Edinburgh FLS980 fluorescence spectrometer equipped with a 370 nm-laser, operating in time-correlated single photon counting mode (TCSPC) with a resolution time of 200 ps. The photoluminescent quantum efficiency in powder form was measured using an integrating sphere with excitation at 365 nm on the Edinburgh FLS980 fluorescence spectrometer.circular dichroism (CD) spectra were recorded by a Chirascan V100 spectropolarimeter in ethanol and acetonitrile solution. A 200 μl portion of each sample was infused into a 1 mm quartz cell and measured at the scan speed of 300 nm min -1 with a bandwidth of 4 nm. A RST electrochemical workstation using a 3-electrode system with a glassy carbon working electrode, a platinum flag counter electrode, and a Ag/AgCl reference electrode with 0.1 M n Bu 4 NPF 6 in CH 2 Cl 2 as the supporting electrolyte were used for cyclic voltammetry measurements. S4
5 Supplementary Figures Figure S1. The experimental and simulated PXRD spectra of 1. Figure S2. The experimental and simulated PXRD spectra of 2. S5
6 Figure S3. The experimental and simulated PXRD spectra of 3. Figure S4. The experimental and simulated PXRD spectra of 4. S6
7 Figure S5. 1 H NMR spectrum of 2 (CDCl 3 ). Figure S6. 1 H NMR spectrum of 3 (CDCl 3 ). S7
8 Figure S7. 1 H NMR spectrum of 4 (CDCl 3 ). 1 H NMR spectra of 2-4 were all recorded in CDCl 3, the integration ratio of 1(benzoic acid) : 2.23( t Bu) for 2; 1.33(alrestatin) : 1.87( t Bu) for 3; 1(Fc) : 1.26( t Bu) for 4 were found, which coincide well with the theoretically calculated value (1 : 2.25 for 2, 1 : 1.4 for 3 and 1 : 1.25 for 4. Figures S5-7). The results showed that the clusters are unchanged and robust in solution. S8
9 Figure S8. FT-IR spectra of 1-7. Figure S9. (a) Ball-stick representation of complex 1. H atoms; the tert-butyl groups and cocrystallized solvent molecules are omitted for clarity. (b) The Ag 20 S 10 cluster. (c) One Ag 4 S square. (d) The three-layer parallel rings (Ag 5 S 5 -Ag 10 -Ag 5 S 5 ). (e) The bilevelinverted Ag 5 S 5 pentagram. (f) One Ag 5 S 5 pentagram. Color code: Ag, green; S, yellow; C, gray; O, red; N, blue. S9
10 Figure S10. Representative TEM images of 2 (a), 3 (b) and 4 (c). Figure S11. Normalized excitation (black, λ em = 617 nm) and emission spectra (red, λ ex = 353 nm) of 2 in the solid state at 83K. S10
11 Figure S12. Temperature-dependent luminescence spectra of 2 (83-163K) excited at 353 nm in the solid state. Figure S13. Luminescence decay traces of 3 (black circle, at 513 nm) and alrestatin (blue circle, at 450 nm) in air after excitation at 370 nm. S11
12 Figure S14. Normalized excitation (black, λ em = 450 nm) and emission spectra (red, λ ex = 275 nm or 377 nm) of alrestatin in the solid state at room temperature. Figure S15. Normalized excitation (black, λ em = 513 nm) and emission spectra (red, λ ex = 372 nm) of 3 in the solid state at room temperature. S12
13 Figure S16. A representation of π-π stacking interaction in complex 3. Figure S17. Temperature-dependent luminescence spectra of 3 (93-293K) excited at 372 nm in the solid state. S13
14 Figure S18. Cyclic voltammogram of complexes 1-4 under same measured conditions (The supporting electrolyte is 0.1 M n Bu 4 NPF 6 in CH 2 Cl 2, the scan rate is 100 mv s -1 ). Figure S19. Crystallographic site disorder of alanine molecule in 5a and 5b. S14
15 Figure S20. The experimental and simulated PXRD spectra of 5a. Figure S21. The experimental and simulated PXRD spectra of 5b. S15
16 Figure S22. The experimental and simulated PXRD spectra of 6a. Figure S23. The experimental and simulated PXRD spectra of 6b. S16
17 Figure S24. The experimental and simulated PXRD spectra of 7a. Figure S25. The experimental and simulated PXRD spectra of 7b. S17
18 Figure S26. Representative TEM images of 5a (a), 6a (b) and 7a (c). Figure S27. 1 H NMR spectrum of 5 (CD 3 OD). S18
19 Figure S28. 1 H NMR spectrum of 6 (CD 3 OD). Figure S29. 1 H NMR spectrum of 7 (CD 3 OD). S19
20 Figure S30. 1 H NMR spectrum of 5 (CD 3 OD). Figure S31. 1 H NMR spectrum of 6 (CD 3 OD). S20
21 Figure S32. 1 H NMR spectrum of 7 (CD 3 OD). Table S1. The integration ratio and chemical shift of H on the ligands of 5-7. Complex (Group) Integration ratio 1 H NMR data Chemical shift (amino acid)/ppm 5 (alanine : t Bu ) 3.99 : , 1.46, 3.76 and (alanine : t Bu ) 3.95 : , 1.44, 3.75 and (valine : t Bu ) 6.99 : , 1.03, 1.06, 1.08, 2.20 and (valine : t Bu ) 7.05 : , 1.05, 1.07, 1.09, 2.22 and (proline : t Bu ) 8.01 : , 1.86, 1.97, 2.21, 3.10, 3.22 and (proline : t Bu ) 7.92 : , 1.89, 1.97, 2.22, 3.12, 3.22 and 3.91 S21
22 Figure S33. UV-vis spectra of 5 and 7 in ethanol and 6 in acetonitrile. Figure S34. CD spectra of L- or D-alanine, L- or D-valine and L- or D-proline in deionized water. S22
23 Table S2. Crystal data and structure refinements for 1 and Empirical formula C 57 H 126 N 12 S 10 Ag 20 O 31 C 109 H 154 N 4 O 21 S 10 Ag 20 Formula weight Temperature/K (10) 220(10) Crystal system monoclinic triclinic Space group I2/a P-1 a/å (2) (2) b/å (14) (3) c/å α/ β/ γ/ Volume/Å (3) (3) (2) (11) (2) (2) (2) (12) Z 4 1 ρcalcg/cm μ/mm F(000) Crystal size/mm Radiation CuKα (λ = Å) CuKα (λ = Å) 2θrange for data collection/ to to 130 Index ranges -24 h 29, -19 k 6, -33 l h 15, -19 k 19, -20 l 20 Reflections collected Independent reflections [R int = , R sigma = ] [R int = , R sigma = ] Data/restraints/parameters 10354/144/ /85/802 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = R 1 = , wr 2 = CCDC Table S3. Crystal data and structure refinements for 3 and Empirical formula C 161 H 166 N 12 O 35 S 10 Ag 20 C 139 H 181 N 5 O 21 Fe 8 S 10 Ag 20 Formula weight Temperature/K 200(10) 100(10) Crystal system triclinic triclinic Space group P-1 P-1 a/å (3) (4) b/å (5) (4) c/å α/ β/ γ/ (5) (4) (2) (2) (2) (19) (17) (2) 3 Volume/Å (2) (17) Z 1 1 ρcalcg/cm μ/mm F(000) Crystal size/mm Radiation CuKα (λ = Å) CuKα (λ = Å) 2θrange for data collection/ to to Index ranges -19 h 18, -21 k 19, -22 l h 18, -19 k 19, -19 l 16 Reflections collected Independent reflections [R int = , R sigma = ] [R int = , R sigma = ] Data/restraints/parameters 17521/31/ /193/999 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = R 1 = , wr 2 = CCDC S23
24 Table S4. Crystal data and structure refinements for 5a and 5b. 5a 5b Empirical formula C 114 H 242 N 24 S 20 Ag 44 O 59 C 114 H 242 N 24 S 20 Ag 44 O 59 Formula weight Temperature/K 150(10) 150(10) Crystal system monoclinic monoclinic Space group P2 1 P2 1 a/å (6) (4) b/å (4) (3) c/å α/ β/ γ/ (6) (4) (2) (15) Volume/Å (5) (3) Z 2 2 ρcalcg/cm μ/mm F(000) Crystal size/mm Radiation MoKα (λ = Å) MoKα (λ = Å) 2θ range for data collection/ to to 50 Index ranges -30 h 30, -22 k 20, -31 l h 30, -18 k 22, -31 l 31 Reflections collected Independent reflections [R int = , R sigma = ] [R int = , R sigma = ] Data/restraints/parameters 39814/744/ /917/2549 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = R 1 = , wr 2 = Flack parameters 0.113(12) 0.106(11) CCDC Table S5. Crystal data and structure refinements for 6a and 6b. 6a 6b Empirical formula C 73 H 154 N 11 S 10 Ag 23 O 28 C 73 H 154 N 11 S 10 Ag 23 O 28 Formula weight Temperature/K 100(2) 100(2) Crystal system monoclinic monoclinic Space group P2 1 P2 1 a/å (6) (6) b/å (9) (10) c/å α/ β/ γ/ (14) (15) (15) (16) Volume/Å (6) (6) Z 2 2 ρcalcg/cm μ/mm F(000) Crystal size/mm Radiation MoKα (λ = Å) MoKα (λ = Å) 2θrange for data collection/ to to Index ranges -16 h 16, -24 k 24, -37 l h 16, -24 k 24, -37 l 37 Reflections collected Independent reflections [R int = , R sigma = ] [R int = , R sigma = ] Data/restraints/parameters 32029/408/ /669/1422 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = R 1 = , wr 2 = Flack parameters 0.030(12) 0.054(14) CCDC S24
25 Table S6. Crystal data and structure refinements for 7a and 7b. 7a 7b Empirical formula C 89 H 174 N 16 S 10 Ag 24 O 35 C 89 H 174 N 16 S 10 Ag 24 O 35 Formula weight Temperature/K 150(10) 150(10) Crystal system monoclinic monoclinic Space group P2 1 P2 1 a/å (3) (16) b/å (2) (15) c/å α/ β/ γ/ (2) (18) (10) (8) Volume/Å (15) (11) Z 2 2 ρcalcg/cm μ/mm F(000) Crystal size/mm Radiation CuKα (λ = Å) CuKα (λ = Å) 2θrange for data collection/ to to Index ranges -22 h 17, -16 k 18, -22 l h 22, -15 k 18, -22 l 19 Reflections collected Independent reflections [R int = , R sigma = ] [R int = , R sigma = ] Data/restraints/parameters 14721/378/ /284/1677 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = R 1 = , wr 2 = Flack parameters 0.046(12) 0.030(11) CCDC R 1 = F o F c F / o. wr 2 = [ w(f o 2 F c 2 ) 2 / w(f o 2 ) 2 ] 1/2 Supplementary References S1. CrysAlis Pro Version (2012). Agilent Technologies Inc. Santa Clara, CA, USA. S2. Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. J. Appl. Cryst. 2015, 48, S3. Sheldrick, G. M. Acta Cryst. A 2008, 64, S4. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A.-K.; Puschmann, H. J. Appl. Cryst. 2009, 42, S5. Sheldrick, G. M. Acta Cryst. C 2015, 71, 3-8. S6. Spek, A. L. Acta Cryst. C 2015, 71, S25
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