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1 Supporting Information for Photocatalytic Reduction of Low Concentration of C 2 Takuya akajima, Yusuke Tamaki, Kazuki Ueno, Eishiro Kato, Tetsuya ishikawa, Kei hkubo, Yasuomi Yamazaki, Tatsuki Morimoto,, * and samu Ishitani * Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, , E-1 -okayama, Meguro-ku, Tokyo, , Japan. Department of Applied Chemistry, School of Engineering, Tokyo University of Technology, 144-1, Katakura, Hachioji, Tokyo, , Japan. PREST, Japan Science and Technology Agency (JST), Honcho, Kawaguchi-shi, Saitama , Japan. * To whom correspondence should be addressed. morimotottk@teu.ac.jp, ishitani@chem.titech.ac.jp Table of Contents 1. Materials, Methods, and Synthetic procedures 2. Supporting Figures (S1-S8) 3. Supporting References (S1-S4) S1
2 1. Materials, Methods, and Synthetic Procedures General procedures IR spectra were obtained using a JASC FT/IR-61 spectrometer at 1 cm 1 resolution. UV Vis absorption spectra were acquired using a JASC V-67 spectrometer. 1 H MR and 13 C MR spectra were obtained using a JEL AL3 or a JEL ECA4II spectrometer. C 2 gas diluted with Ar (.5%, 1%, 5%, 1%, and 5% C 2 gas) was prepared from pure C 2 (purity %) or 1% C 2 -Ar and pure Ar using a mass flow meter. Materials,-Dimethylformamide (DMF) was dried over 4 Å molecular sieves and distilled under reduced pressure. TEA was distilled under reduced pressure. These compounds were stored under an Ar atmosphere before use. 1,3-Dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole (BIH) S1 and Ru-Re-DMF S2 were prepared according to the literature. Commercially available reagents (reagent grade) were used without further purification. Estimation of the equilibrium constants Various amounts of a C 2 -saturated DMF solution (the concentration of C 2 is.2 M) S3 was added to sealed sample tubes, which were then filled with DMF TEA (5:1 v/v) solutions containing Ru-Re-DMF and Ru-Re-C 2 H 4 R 2 (total concentrations were 3.7 mm) using a shielded syringe. The concentrations of Ru-Re-DMF, Ru-Re-C 2 H 4 R 2, and Ru-Re-C()C 2 H 4 R 2 were evaluated from the peak areas corresponding to each of the complexes in the IR spectra. S4 The peaks could be separated by curve fitting using a linear combination of the Gaussian function and the Lorentzian function (Figure S1). Herein, the equilibrium constants, K LS and K C2, were defined as follows: Photocatalytic reactions Photocatalytic systems for reducing low concentrations of C 2 Photocatalytic reactions were conducted with a solution of Ru-Re-DMF and Ru-Re-C 2 H 4 R 2 (total concentration:.5 mm) in DMF TEA (5:1 v/v, total 2 ml) containing BIH (.1 M). Ar-based gas containing various concentrations of C 2 was bubbled into a gas-flow cell, as shown in Figure S2. After bubbling the reaction mixture with gas for 3 min, the solution was irradiated at ex = 48 nm using a 3 W Xeon lamp (Asahi Spectra MAX-32). During irradiation, the gas flow (1 ml min 1 ) was continued. The evolved C and H 2 contained in the outlet gas were analyzed by an IFIC 3 Micro-GC equipped with a TCD detector. The turnover numbers (T C and T H2 ) are defined as the [amount of evolved C or H 2 ]/[amount of the photocatalyst]. The S2
3 reproducibility of the photocatalytic C formation was confirmed in the case under 1% C 2 for 5-h irradiation, and the experimental error was within 3% between two same experiments. Measurement of quantum yield The quantum yield for C formation in the photocatalytic reduction of C 2 under a pure C 2 atmosphere was determined as follows: DMF TEA (5:1 v/v, 4 ml) solutions of Ru-Re-DMF and Ru-Re-C 2 H 4 R 2 (total concentration:.5 mm) containing BIH (.1 M) were bubbled with pure C 2 gas in 11 ml necked quartz cubic cells (path length: 1 cm). The solutions were irradiated at ex = 48 nm (light intensity: einstein s -1 ) using a 3 W Xeon lamp (Asahi Spectra MAX-32) with a band-pass filter for T = 3, 6, and 9 min in a Shimadzu QYM-1 Photoreaction Quantum Yield Evaluation System. The evolved C was analyzed by GC-TCD (GL science GC323), and the photon number absorbed by the reaction solution was obtained from the light intensity (I(t)) and absorbance at 48 nm (A(t)) by the equation below, which were continuously measured during the photocatalytic reaction. The (internal) quantum yield for C formation could be estimated at 5% from the mean value of [amount of evolved C molecules]/[amount of absorbed photons] (Figure S6). amount of absorbed photon = I(t) (1 1 A(t) )dt Photochemical reduction of [Ru(dmb) 3 ] 2+ by BIH in the presence of a proton source A 4 ml DMF solution containing [Ru(dmb) 3 ](PF 6 ) 2 (.5 mm), BIH (.1 M), and tri(n-propyl)ammonium hexafluorophosphate (25 mm) in a 11 ml necked quartz cubic cell (path length: 1 cm) was irradiated at 48 nm (light intensity: einstein/s) under an Ar atmosphere. UV Vis spectra were obtained using a Shimadzu QYM-1 Photoreaction Quantum Yield Evaluation System during the photoreaction to monitor formation of the one-electron-reduced species (Figure S7). Estimation of C 2 concentrations in a C 2 -saturated DMF-TEA (5:1 v/v) solution and in a DMF-TEA (5:1 v/v) solution bubbled with diluted C 2 gas A DMF-TEA (5:1 v/v) mixed solution was bubbled with pure C 2 for 2 min. This C 2 -saturated solution (1 ml) was added to a Ba(H) 2 aqueous solution (.25 M, 25 ml) giving precipitation of BaC 3. The resulting solution was back-titrated with a standardized.1 M HCl solution, and ph was monitored by a ph meter during the titration. In order to exclude the influence of TEA, a mixed DMF-TEA (5:1 v/v) solution without C 2 bubbling was also titrated. The concentration of C 2 in the saturated DMF-TEA (5:1 v/v) solution was determined as.14 M. The equilibrated concentration of C 2 in the mixed DMF-TEA solution during bubbling with diluted C 2 gas was evaluated by using a Re(I) tricarbonyl complex with a labile monodentate ligand, which can be a good indicator to monitor C 2 concentration in a DMF solution containing TEA. S4 Concentrations of C 2 in DMF-TEA (5:1 v/v) solutions bubbled with dilute C 2 were obtained by using the equilibrium constants (K LS and K C2 ) as shown below and concentrations of three Re(I) complexes, i.e., the Re(I) complexes coordinated by deprotonated TEA or DMF and the aminoethylcarbonato Re(I) complex. The concentrations of the complexes could be estimated S3 T
4 from the peak area of each Re(I) complex in the IR spectrum of the solution after bubbling with the dilute C 2. The IR spectra of the solutions bubbled with 1%, 1%, and 1% C 2 gas for 2 min are shown in Figure S8a-c. Based on these data, the C 2 concentrations for the three conditions were obtained as.22 M,.16 M, and.13 M, respectively. The C 2 concentrations in the solution showed a good linearity with the partial pressure of C 2 over the wide range of C 2 pressure (Figure S8d). S4
5 absorbance absorbance 2. Supporting Figures Figure S1. IR spectra (black solid line) of the equilibrated mixture of Ru-Re-DMF, Ru-Re-C 2 H 4 R 2, and Ru-Re-C()C 2 H 4 R 2 (total concentration was 3.7 mm) in DMF TEA (5:1 v/v) with the fitting curves (green solid lines) and the corresponding components, where black, blue, and red dotted lines denote the curves of Ru-Re-DMF, Ru-Re-C 2 H 4 R 2, and Ru-Re-C()C 2 H 4 R 2, respectively. Initial C 2 concentrations in the solution were set at (a) mm and (b) 1.1 mm. (a).6 (b) wavenumber / cm wavenumber / cm 1 S5
6 Figure S2. 13 C MR spectra of Ru-Re-C()C 2 H 4 R 2 with (black line) and without (red line) 1 H decoupling under a 13 C 2 atmosphere. The three bond carbon-proton coupling with 3 J CH = 3.3 Hz confirmed the formation of Ru-Re-C()C 2 H 4 R 2 in a DMF-TEA solution under a C 2 atmosphere. H H 2+ 3 J CH = 3.3 Hz Ru 13 C Re C C C (CH 2 CH 2 H) 2 Ru-Re-C()C 2 H 4 R d / ppm S6
7 Figure S3. Gas-flow reaction system for photocatalytic reduction of C 2. S7
8 amount of C / mmol concentration of C / ppm Figure S4. Turnover number (T C ) (a) and C concentration in the outlet gas (b) for 26 h in photocatalytic reactions using Ru-Re-DMF and Ru-Re-C 2 H 4 R 2 under 1% C 2 (blue) and 1% C 2 (green) atmosphere. (a) 12 1% 12 (b) 3 T C 8 4 1% % 1% Irradn. time / h Irradn. time / h 25 S8
9 amount of C / mmol concentration of C / ppm Figure S5. Turnover number (T C ) (a) and C concentration in the outlet gas (b) for 19 h in photocatalytic reactions using Ru-Re-DMF and Ru-Re-C 2 H 4 R 2 under 1% C 2 (blue), 5% C 2 (purple), 1% C 2 (green), 1% C 2 (orange), and.5% C 2 (red) atmospheres. (a) 1 1% 1 (b) 3 T C % 1.%.5% 1% % 5% 1.% 1%.5% Irradn. time / h Irradn. time / h S9
10 amount of evolved C / mmol absorbance Figure S6. Measurement of the quantum yield of C formation in the photocatalytic reduction of C 2 using Ru-Re-C()C 2 H 4 R 2 (.5 mm) under a 1% C 2 atmosphere. (a) Dependence of the C formation on amounts of absorbed photons by the reaction solution: irradiation times were 3, 6, and 9 min. (b) UV Vis absorption spectral changes of the reaction solution during irradiation. 2+ Ru Re C C C (CH 2 CH 2 H) 2 / hv (48 nm) (a) 12.5 C 2 Ru-Re-C()C 2 H 4 R 2 DMF/TEA (5:1 v/v), BIH (.1 M) (b) 3 C F = nm amount of absorbed photon / meinstein wavelength / nm S1
11 absorbance Dabsorbance Figure S7. (a) UV Vis absorption spectral changes of the DMF TEA (5:1 v/v) solution containing [Ru(dmb) 3 ](PF 6 ) 2 (.5 mm), BIH (.1 M), and tri(n-propyl)ammonium hexafluorophosphate (25 mm) during irradiation at ex = 48 nm (light intensity: einstein/s) for 1 min and (b) differential UV Vis absorption spectra between after and before the irradiation. (a) 1. (b) wavelength / nm wavelength / nm 8 S11
12 absorbance [C 2 ] / M absorbance absorbance Figure S8. IR spectra (black solid lines) of the equilibrated mixture of Re-DMF, Re-C 2 H 4 R 2, and Re-C()C 2 H 4 R 2, of which total concentration was 5. mm, in DMF TEA (5:1 v/v) by bubbling with 1% (a), 1% (b), and 1% (c) C 2 gas. The fitting curve is shown by green solid, and the corresponding peaks attributed to Re-DMF, Re-C 2 H 4 R 2, and Re-C()C 2 H 4 R 2 were shown in black, blue, and red dotted lines, respectively. The good linearity between the C 2 concentrations in the solution and the partial pressure of C 2 is shown in (d). (a) 1.2 (b) wavenumber / cm wavenumber / cm 1 (c) (d) % % wavenumber / cm 1 1.% P C2 / hpa 1 S12
13 3. Supporting References S1. Tamaki, Y.; Koike, K.; Morimoto, T.; Ishitani,. J. Catal. 213, 34, S2. Kato, E.; Takeda, H.; Koike, K.; hkubo, K.; Ishitani,. Chem. Sci. 215, 6, S3. Konno, H.; Kobayashi, A.; Sakamoto, K.; Fagalde, F.; Katz,. E.; Saitoh, H.; Ishitani,. Inorg. Chim. Acta 2, 299, S4. Morimoto, T.; akajima, T.; Sawa, S.; akanishi, R.; Imori, D.; Ishitani,. J. Am. Chem. Soc. 213, 135, S13
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