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1 Supporting information for A Coordination Gelator that Shows a Reversible Chromatic Change and a Sol-Gel Phase Transition Behavior upon xidative / Reductive Stimuli Shin-ichiro Kawano, orifumi Fujita, and Seiji Shinkai* Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, , akozaki, igashi-ku, Fukuoka , Japan - Contents list- 1. Synthesis of 1, 2 p. S MR spectra of 1, 2 p. S4,S5 3. T gel plot vs. [Cu(I)]/[1] p. S5 4. Various temperature-cd spectra of p. S6 Cu(I) 1 2 complex gel 5. Absorption and CD spectra p. S6 of reductively produced Cu(I) 1 2 complex gel 6. TEM image of reductively produced p. S7 Cu(I) 1 2 complex gel 7. Gelation properties of 1 and Cu(I) 1 2 complex p. S7 8. EPR spectra of the sol and the gel states of the Cu(I) 1 2 complex and UV spectra of the oxidized gel of the Cu(I) 1 2 complex p. S8 S1
2 1. Synthesis of 1, 2 2 C 2 C 2 2 Cl dry C 2 Cl Cl * 2 C 2 C 2 2 dry C 2 Cl 2 2 * 4 C C SCl 2 ClC CCl 3 TEA dry C 2 Cl 2 R 1 C CR 1 1; Bip-Chol 5 R 1 = 4 TEA dry C 2 Cl 2 R 2 C CR 2 2; Bip-2-Etex R 2 = * Scheme S1 Materials All starting materials and solvents were purchased from Aldrich or Tokyo Kasei Chemicals and used as received. 3β- Cholest-5-en-3yl--(2-aminoethyl) carbamate (3) 1, 2-ethylhexyl-(2-aminoethyl)carbamate (4), and 2,2 -bipyridine-4,4 - diacidchloride (5) 2 were prepared according to the literature reported previously and identified by IR and 1 MR spectral S2
3 evidence. Synthesis of 1 3 (2.4 g, 5.1 mmol, 2.5 equiv) and triethylamine (1.2 ml, 8.6 mmol, 4.2 equiv) were dissolved in dry C 2 Cl 2 (50 ml) and cooled to 0 ºC. A dry C 2 Cl 2 solution of 5 (70 ml) was added dropwise during 1.5 hours. The reaction mixture was stirred for overnight at room temperature. The reaction mixture was washed with Cl aq. (0.1 mol dm -3 ) and saturated ac 3 aq., and then, twice with water and dried over a 2 S 4. The solvent was removed from the reaction mixture by evaporation and the residue was purified by column chromatography (Si 2 ; CCl 3 /C 3 = 30 /1) to afford 1 (0.97 g, 41%) as a colorless solid. Mp ºC; 1 MR (600 Mz, TMS, CDCl 3 ) δ 0.67 (s, 6, C 3 ), (m, 12, C 3 ), (m. 68, C and C 2 ), (m, 4, C 2 C), 3.63 (q, J = 5.3 z, 4, ArCC 2 ), 4.56 (sep, J = 5.0 z, 2, CC 2 ), 5.10 (br, 2, ArC), (m, 2, C=C), 7.51 (br, 2, C), 7.78 (d, J = 4.3 z, 2, Ar), 8.75 (s, 2, Ar), 8.81 (d, J = 4.8 z, 2, Ar); MS (MALDI-TF, matrix; dithranol): [M + ] + ; calcd [M + ] + ; EA calcd for C CCl 3 : C 73.64, 9.26, 7.14; found C 73.57, 9.25, Synthesis of 2 4 (0.78 g, 3.6 mmol, 2.2 equiv./ 5) and TEA (1.0 ml, 7.1 mmol, 4.3 equiv./ 5) were dissolved in dry C 2 Cl 2 (40 ml) and cooled to 0 ºC. A solution of 5 in dry C 2 Cl 2 (60 ml) was added dropwise during 2.0 hours. The reaction mixture was stirred from 0 ºC to room temperature for overnight. The mixture was washed with 0.1 -Cl aq., saturated ac 3 aq. and twice with water and dried over a 2 S 4. The solvent was removed by evaporation and the residue was purified by column chromatography (Si 2 ; CCl 3 /Me, 30 :1) to afford 1 (0.74 g, 70%) as a colorless solid. Mp ºC; 1 -MR (600 Mz, TMS, CDCl 3 ) δ 0.84 (t, J = 5.5 z, 12, Me), (m, 16, C 2 ), (m. 2, C), (m, 4, C 2 C), (m, 4, ArCC 2 ), (m, 4, CC 2 ), 5.17(br, 2, C), 7.45 (br, 2, ArC), 7.75 (d, J = 4.4 z, 2, Ar), 8.73 (s, 2, Ar), 8.78 (d, J = 4.6 z, 2, Ar); MS (MALDI-TF, matrix; dithranol): calcd [M + ] +, found [M + ] + ; EA: calcd for C : C 63.73, 8.18, 13.11; found C 63.70, 8.17, S3
4 2. 1 MR spectrum of 1 Figure S Mz 1 MR spectrum of 1 in CDCl 3 S4
5 Figure S Mz 1 MR spectrum of 2 in CDCl 3 3. T gel plot vs. [Cu(I)] /[1] (a) Tgel / ºC Gel 120 Sol [1] / g dm -3 (b) T gel / ºC [Cu(I)] / [1] Figure S3. Plots of T gel vs. (a) [1], (b) [Cu(I)] / [1] in 1-PrC: (b) [1] = 6.1 mmol dm -3, [Cu(MeC) 4 PF 6 ] = 3.0 mmol dm -3. S5
6 4. Various temperature-cd spectra of Cu(I) 1 2 complex gel 10 5 CD / mdeg Wavelength / nm Figure S4. Various temperature-cd spectra of the gel of 1 + Cu(MeC) 4 PF 6 ; 1-PrC, [1] = 4.3 mmol dm -3, [Cu(MeC) 4 PF 6 ] = 2.2 mmol dm -3, 20 to 70 ºC. The contribution of LD (linear dichroism) was negligible under the same measurement conditions. 5. Absorption and CD spectra of reductively produced Cu(I) 1 2 complex gel (a) (b) Absorbance / a. u. Reduced Cu(I) gel Cu(I) gel CD / a. u. Cu(I) gel Reduced Cu(I) gel Wavelength / nm Wavelength / nm Figure S5. (a) Absorption and (b) CD spectra of the gel of 1 and a half molar equivalent of Cu(MeC) 4 PF 6 (the green line), the gel of 1, a half molar equivalent of Cu(Tf) 2 and about 1.6 molar equivalent of ascorbic acid (the blue line); 1-PrC, [1] = 8.7 mmoldm -3, 25 ºC. For the CD measurements, the contribution of LD was negligible under the same measurement conditions. S6
7 6. TEM image of reductively produced Cu(I) 12 complex gel nm nm Figure S6. TEM image of 1-PrC gels prepared from 1 (8.7 mmol dm-3) + Cu(Tf)2 (4.3 mmol dm-3) + ascorbic acid (6.9 mmol dm-3); stained with phosphotungstic acid aqueous solution (20 g dm-3). 7. Gelation properties of 1 and Cu(I) 12 complex Table S1. Gelation properties of 1, [Cu(1) 2]+ complex and [Cu(2)2]+ complex at 25 ºC. a Stateb Solvent 1 I Acetonitrile 1 + Cu(I) I 1-PrC Benzonitrile G G G Gc The other solventsd Gc S a Concentration of [1 or 2] is 8.7 mmol dm-3 (10 g dm-3), [Cu(MeC) 4PF 6] = 4.3 mmol dm-3. b G: gel, PG: partial gel, P: precipitation, I: insoluble when heated. c Gel at [1] = 22 mmol dm-3 (25 g dm-3), [Cu(MeC) 4PF 6] = 11 mmol dm-3. dbenzene, toluene, p-xylene, C Cl, CCl, TF, butanol, 2-propanol, 1-propanol, ethanol. S7
8 8. EPR spectra of the sol and the gel states of the Cu(I) 1 2 complex and UV spectra of the oxidized gel of the Cu(I) 1 2 complex (a) state 1 state 2 state 3 Cooling Δ BF 4, Δ AsA, Δ Sol Gel Sol EPR silent EPR silent EPR active Cu(I) Cu(I) Cu(II) (b) (c) (i) (ii) Absorbance / A.U. (i) (ii) B / G Wavelength / nm Figure S7. (a) Photographs of the chromatic change and phase transition behavior of 1-PrC gel of Cu(I) 1 2. Conditions: see the manuscript. (b) EPR spectra of (i) 1-PrC gel prepared from equiv Cu(MeC) 4 PF 6, [1] = 8.7 mmol dm -3 in 1-PrC at 25 ºC and (ii) the precipitate prepared by oxidation of above 1-PrC gel of Cu(I) 1 2 with 1.6 equiv BF 4. (c) UV-Vis absorption spectra of (i) the 1-PrC gel prepared from equiv Cu(MeC) 4 PF 6, [1] = 8.7 mmol dm -3 in 1-PrC at 25 ºC and (ii) the KBr pellet with the precipitate prepared from equiv Cu(MeC) 4 PF 6, and 1.6 equiv BF 4, [1] = 8.7 mmol dm -3 in 1-PrC at 25 ºC. (1) Ishi-i, T.; Iguchi, R.; Snip, E.; Ikeda, M.; Shinkai, S. Langmuir 2001, 17, (2) Garelli,.; Vierling, P. J. rg. Chem. 1992, 57, S8
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