[Ag-Ag] 2+ Unit-Encapsulated Trimetallic Cages: One-pot Syntheses and Modulation of Argentophilic Interactions by the Uncoordinated Substituents
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1 [Ag-Ag] 2+ Unit-Encapsulated Trimetallic Cages: One-pot Syntheses and Modulation of Argentophilic Interactions by the Uncoordinated Substituents Guo-Xia Jin,,a Gui-Ying Zhu,,a Yan-Yan Sun, c Qing-Xiu Shi, a Li-Ping Liang, a Hai-Ying Wang, b Xiang-Wen Wu, a and Jian-Ping Ma*,a a College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging, Key Laboratory of Molecular and ano Probes, Ministry of Education, Shandong ormal University, Jinan , People s Republic of China b College of Chemistry and Materials Science, Sichuan ormal University, Chengdu , People s Republic of China c QiLu Pharmaceutical (Haian) Co., Ltd., Haikou, Hainan , People s Republic of China These authors contributed equally. Experimental General methods Chemicals and solvents used in the syntheses were obtained from commercial sources and used without further purification. 1 H MR data were collected using a BRUKER AVACE 400 spectrometer. Chemical shifts are reported in δ relative to TMS. Element analyses were performed on a Perkin-Elmer Model 240C analyzer. Infrared (IR) spectra were obtained in the cm -1 range using a BIO-RAD FTS-40 infrared spectrometer. Powder X-ray diffraction patterns were collected using a Bruker D8 ADVACE diffractometer (Cu K = Å) with an operating power of 40 Kv and fixed divergence slit of 0.76 mm. The data were collected in the range of 2θ = Photoluminescence spectra were measured on a FLS920 Fluorescence Spectrophotometer (slit width: 5 nm; sensitivity: high). 4-amino-3-(2-pyridyl)-5-mercapto-1,2,4-triazole (S3) 1 and 1,3,5-tris(bromomethyl)-2,4,6-trimethyl benzene (S4) 2 were prepared according to a modified S1
2 method in literature. O CHH 2 KOH, CS 2 EtOH O S H 2 H 2 H 2 O CHHCS - K + H 2 SH H 2 S1 S2 S3 KOH S Br H 2 (HCHO) n, KBr H 2 SO 4, HOAc Br Br S S H 2 L S4 Synthesis of 1,3,5-tris(4-amino-5-pyridin-2-yl-1,2,4-triazol-3-ylmercaptomethyl)-2,4,6-trimethyl benzene (L) S3 (11.59 g, 60 mmol) and KOH (5.9 g, 120 mmol) were dissolved in 100 ml methanol and stirred at room temperature for 20 min. 1, 3, 5-tris(bromomethyl)-2, 4, 6-trimethyl benzene S4 (3.99 g, 10 mmol) was added and the mixture was stirred at room temperature for 24 h. The solvent was removed by rotary evaporation. The crude product was further purified by chromatography on a silica gel column with dichloromethane/methanol (20:1, v/v) to give a white solid after solvent removal under vacuum. Yield: 5.48 g (75%). 1 H MR (400 MHz, 25 o C, DMSO-d 6, ppm): 8.73 (d, J = 4 Hz, 6H, -C 5 H 4 ); 8.13 (d, J = 8 Hz, 6H, -C 5 H 4 ); 8.02 (t, J = 8 Hz, 6H, -C 5 H 4 ); 7.54 (t, J = 8 Hz, 6H, -C 5 H 4 ); 6.65 (s, 12H, -H 2 ); 4.58 (s, 12H, -SCH 2 -); 2.53 (s, 18H, -CH 3 ). IR (cm -1 ): 3276 (s), 3171 (s), 3053 (w), 2966 (w), 1625 (m), 1591 (s), 1567 (m), 1450 (vs), 1422 (s), 1356 (m), 1010 (s), 789 (s), 729 (m). Preparation of complex [Ag 5 (L) 2 (SbF 6 ) 5 ] 3C 4 H 8 O 2 (1) A solution of AgSbF 6 (10 mg, mmol) in ethanol(7 ml) was layered carefully onto a solution of L (10 mg, mmol) in 1,4-dioxane (6 ml) in a 1.5-cm in diameter glass tube. The solution was left for a week at room temperature, and colorless crystals were collected (11.5 mg, 57%). 2.1 equiv. of Ag(I) is the most suitable ratio for obtaining the single-crystals 1 of the best quality. 1 H MR (400 MHz, 25 o C, DMSO-d 6, ppm): 8.79 (d, J = 4 Hz, 6H, -C 5 H 4 ); 8.27 (d, J = 8 Hz, 6H, -C 5 H 4 ); 8.09 (t, J = 8 Hz, 6H, -C 5 H 4 ); 7.63 (t, J = 8 Hz, 6H, -C 5 H 4 ); 6.89 (s, 12H, -H 2 ); 4.45 (s, 12H, -SCH 2 -); 2.18 (s, 18H, -CH 3 ). IR (cm -1 ): 3636 (w), 3342 (w), 3186 (w), 1625 (m), 1593 (m), 1475 (m), 1444 (s), 1009 (m), 783 (m), 660 (vs). Elemental analysis Calcd (%) for C 78 H O 6 S 6 Ag 5 Sb 5 F 30 : C 30.46, H 2.95, 1.37; S2
3 Found: C 30.90, H 3.43, Preparation of complex [Ag 5 (L 1 ) 2 (BF 4 ) 5 ] 2(C 3 H 6 O) 5(CHCl 3 ) (2) A solution of AgBF 4 (4 mg, mmol) in acetone (7 ml) was layered carefully onto a solution of L (10 mg, mmol) in CHCl 3 (6 ml) in a 1.5-cm in diameter glass tube. The solution was left for a week at room temperature, and colorless crystals were collected (8.4 mg, 64%). 1.5 equiv. of Ag(I) is the most suitable ratio for obtaining the single-crystals 2 of the best quality. 1 H MR (400 MHz, 25 o C, DMSO-d 6, ppm): 8.71 (d, J = 4 Hz, 6H, -C 5 H 4 ); 8.04 (d, J = 4 Hz, 12H, -C 5 H 4 ); 7.58 (q, J = 4 Hz, 6H, -C 5 H 4 ); 4.40 (s, 12H, -SCH 2 -); 2.33 (s, 18H, -CH 3 ); 2.22 (br. s, 18H, -CH 3 ); 1.86 (s, 18H, -CH 3 ). IR (cm -1 ): 3020 (w), 1710 (w), 1625 (m), 1596 (m), 1475 (m), 1433 (s), 1373 (m), 1060 (vs), 621 (s). Elemental analysis Calcd (%) for C 95 H 107 Ag 5 30 O 2 S 6 Cl 15 F 20 B 5 : C 37.78, H 3.57, 1.39; Found: C 38.01, H 3.91, Preparation of complex [Ag 5 (L 1 ) 2 (ClO 4 ) 5 ] 2(C 3 H 6 O) 5(CHCl 3 ) (3) AgClO 4 (5 mg, mmol) was used instead of AgBF 4, colorless needle crystals were collected (8.2 mg, 52%). 1 H MR (400 MHz, 25 o C, DMSO-d 6, ppm): 8.69 (d, J = 4 Hz, 6H, -C 5 H 4 ); (m, 12H, -C 5 H 4 ); 7.56 (t, 6H, -C 5 H 4 ); 4.42 (s, 12H, -SCH 2 -); 2.31 (s, 18H, -CH 3 ); 2.26 (br. s, 18H, -CH 3 ); 1.86 (s, 18H, -CH 3 ). IR (cm -1 ): 3021 (w), 1710 (w), 1626 (m), 1596 (m), 1470 (m), 1428 (s), 1373 (m), 1090 (vs), 621 (s). Elemental analysis Calcd (%) for C 95 H 107 Ag 5 30 O 22 S 6 Cl 20 : C 37.00, H 3.50, 1.36; Found: C 37.10, H 3.85, Preparation of complex [Ag 5 (L 2 ) 2 (ClO 4 ) 5 ] (C 4 H 8 O 2 ) (solvent) (4) A solution of AgClO 4 (7 mg, mmol) in cyclohexanone (7 ml) was layered carefully onto a solution of L (10 mg, mmol) in 1,4-dioxane (6 ml) and chloroform (1 ml) in a 1.5-cm in diameter glass tube. The solution was left for 5 days at room temperature, and pale yellow crystals were collected (16.5 mg, 79%). 1 H MR (400 MHz, 25 o C, DMSO-d 6, ppm): 8.70 (d, J = 4 Hz, 6H, -C 5 H 4 ); 8.03 (s, 12H, -C 5 H 4 ); 7.58 (s, 6H, -C 5 H 4 ); 4.41 (br. s, 12H, -SCH 2 -); 2.61 (s, 12H, -CH 2 ), 2.25 (t, 12H, -CH 2 ), 2.11 (s, 18H, -CH 3 ), (m, 36H, -CH 2 ). IR (cm -1 ): 3021 (w), 2940 (w), 2862 (w), 1700 (w), 1616 (m), 1596 (m), 1470 (m), 1431 (s), 1089 (vs), 622 (s). Elemental analysis Calcd (%) for C 106 H 122 Ag 5 Cl 5 30 O 22 S 6 C: 47.17, H 4.56, 1.56; Found: C 46.95, H 4.40, S3
4 Figure S1. 1 H MR spectrum of ligand L. Figure S2. 1 H MR spectrum of complex 1. S4
5 Figure S3. 1 H MR spectrum of complex 2. Figure S4. 1 H MR spectrum of complex 3. S5
6 Figure S5. 1 H MR spectrum of complex 4. Figure S6. ORTEP figure of complex 1. S6
7 Figure S7. Ball-and-stick model of cage 1, showing the Ag- and Ag π interactions. Figure S8. ORTEP figure of complex 2. S7
8 Figure S9. ORTEP figure of complex 3. Figure S10. ORTEP figure of complex 4. S8
9 Figure S11. Titration experiments by the addition of a solution of AgSbF 6 into a solution of L in DMSO-d 6. S9
10 Table S1. Crystal data and structure refinement for Chemical formula C 78 H O 6 S 6 Ag 5 Sb 5 F 30 C 95 H 107 Ag 5 B 5 Cl 15 F O 2 S 6 Formula weight Temperature/K (10) (10) Wavelength/ Å Crystal system Monoclinic Monoclinic Space group C2/c C2/c a/å (3) (6) b/å (11) (4) c/å (8) (8) α/ β/ (3) (4) γ/ Volume/ Å (6) (12) Z 4 4 ρ calc / g cm μ/ mm F(000) Reflections collected/ 40976/ / unique [R int = ] [R int = ] Data/ parameter restraints/ 12030/91/ /32/815 GOOF R[I>2sigma(I)] R 1 = , wr 2 = R 1 = , wr 2 = R(all data) R 1 = , wr 2 = R 1 = , wr 2 = S10
11 3 4 Chemical formula C 95 H 107 Ag 5 30 O 22 S 6 Cl 20 C 106 H 122 Ag 5 Cl 5 30 O 22 S 6 Formula weight Temperature/K (10) 173(2) Wavelength/ Å Crystal system Monoclinic Monoclinic Space group C2/c P2 1 /c a/å (7) (4) b/å (3) (5) c/å (9) (8) α/ β/ (6) (2) γ/ Volume/ Å (11) (9) Z 4 8 ρ calc / g cm μ/ mm F(000) Reflections collected/ 25267/ /53714 unique [R int = ] [R int = ] Data/ restraints/ parameter 11800/26/ /2/3135 GOOF R[I>2sigma(I)] R 1 = , wr 2 = R1 = , wr2 = R(all data) R 1 = , wr 2 = R1 = , wr2 = Table S2. Selected bond lengths (Å) and angles (ᵒ) in complexes Ag1' 11' 2.30(3) Ag (9) Ag (16) Ag (8) S11
12 Ag (16) Ag (8) Ag (15) Ag (9) 7 1 Ag (8) Ag (9) 7 1 Ag (5) 2 Ag (3) 7 1 Ag (6) 2 Ag (4) 12 Ag (6) 1 1 Ag (5) 10 1 Ag (9) 2 1 Ag (3) 12 Ag (7) 3 Ag (3) 13 Ag (4) 13 Ag (4) 2 Ag(1) Ag(1) (12) Ag(1) (3) 2.233(6) Ag(1) (8) 2.265(6) Ag(1) (13) 2.262(6) Ag(2) (1) 2.363(7) Ag(2) (2) 2.299(7) Ag(2) (6) (8) Ag(2) (7) (6) Ag(3) (11) 2.421(7) Ag(3) (12) 2.265(7) (13) Ag(1) (8) 116.0(2) (2) Ag(2) (1) 71.2(2) (3) Ag(1) (8) 123.1(3) (1) Ag(2) (6) (3) (3) Ag(1) (13) 120.9(3) (2) Ag(2) (6) (3) (12) Ag(3) (11) (3) (7) 1 Ag(2) (2) 120.2(2) (12) 1 Ag(3) (11) 155.6(3) (7) 1 Ag(2) (1) 154.6(3) (12) 1 Ag(3) (12) 127.4(3) (7) 1 Ag(2) (6) (2) (11) 1 Ag(3) (11) 98.4(4) (12) Ag(3) (11) 70.6(2) (12) 1 Ag(3) (11) (2) 3 Ag(1) Ag(1) (11) Ag(2) (1) 2.378(7) Ag(1) (3) 2.233(6) Ag(2) (2) 2.294(6) Ag(1) (8) 2.267(6) Ag(2) (6) (7) Ag(1) (13) 2.261(6) Ag(2) (7) (6) Ag(3) (11) 2.393(7) Ag(3) (12) 2.262(7) S12
13 (3) Ag(1) (8) 123.2(2) (1) Ag(2) (6) (3) (3) Ag(1) (13) 121.1(2) (2) Ag(2) (1) 71.4(2) (13) Ag(1) (8) 115.7(2) (2) Ag(2) (6) (3) (11) Ag(3) (11) (3) (7) 1 Ag(2) (1) 152.8(2) (12) Ag(3) (11) 71.1(2) (7) 1 Ag(2) (2) 120.0(2) (12) 1 Ag(3) (11) 156.4(2) (7) 1 Ag(2) (6) (2) (12) 1 Ag(3) (12) 125.3(3) 4 Ag1 Ag (3) Ag (3) Ag (2) Ag (3) Ag (2) Ag (3) Ag (3) Ag (3) Ag (2) Ag (2) Ag (2) Ag (2) Ag (2) Ag (3) Ag (2) Ag (3) Ag (3) Ag (3) Ag (2) 11 Ag (9) 11 Ag (9) 1 Ag (9) 11 Ag1 Ag (6) 1 Ag1 Ag (6) 6 Ag1 Ag (6) 26 Ag (10) 26 Ag (10) 16 Ag (10) 26 Ag2 Ag (6) 12 Ag (9) 12 Ag (9) 27 Ag (9) 12 Ag (8) 22 Ag (9) 2 Ag (9) 22 Ag (9) 5 Ag (10) 7 Ag (10) 20 Ag (10) 7 Ag (9) S13
14 20 Ag (9) 10 Ag (11) Symmetry transformations used to generate equivalent atoms: 1: 1 -X, +Y, 1/2-Z; 2 1-X, 2-Y, 1-Z; 3 1-X, +Y, 1/2-Z. 2: 1 2-X, +Y, 1/2-Z; 2 -X, +Y, 1/2-Z; 3 1-X, +Y, 1/2-Z. 3: 1 2-X, +Y, 1/2-Z; 2 -X, +Y, 1/2-Z; 3 1-X, +Y, 1/2-Z. Reference 1. Reid, J. R.; Heindel,. D. Improved syntheses of 5-substituted-4-amino-3-mercapto-(4H)-1,2,4-triazoles. J. Heterocyclic Chem. 1976, 13, Liu, G.; Wang, Y.; Shen, C.; Ju, Z.; Yuan, D. A facile synthesis of microporous organic polymers for efficient gas storage and separation J. Mater. Chem. A 2015, 3, S14
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