Rapid Synthesis of Thiophene‐Based,Organic Dyes for Dye‐Sensitized Solar Cells (DSSCs) by a One‐Pot,Four‐Component Coupling Approach |
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| Authors: | Keisuke Matsumura Soichi Yoshizaki Dr. Masato. M. Maitani Prof. Yuji Wada Dr. Yuhei Ogomi Prof. Shuzi Hayase Dr. Tatsuo Kaiho Dr. Shinichiro Fuse Dr. Hiroshi Tanaka Prof. Takashi Takahashi |
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| Affiliation: | 1. Department of Applied Chemistry, Tokyo Institute of Technology, 2‐12‐1, Ookayama, Meguro‐ku, Tokyo 152‐8552 (Japan);2. Graduate School of Life Science and Systems Engineering, Kyusyu Institute of Technology, Fukuoka 808‐0196 (Japan);3. Kanto Natural Gas Development Co., Ltd. Brine Resources Research & Development Division, Chiba 297‐8550 (Japan);4. Present address: Chemical Resources Laboratory, Tokyo Institute of Technology, 4259 Nagatsuta‐cho, Midori‐ku, Yokohama 226‐8503 (Japan);5. Yokohama College of Pharmacy, 601, Matano‐cho, Totsuka‐ku, Yokohama 245‐0066 (Japan) |
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| Abstract: | This one‐pot, four‐component coupling approach (Suzuki–Miyaura coupling/C?H direct arylation/Knoevenagel condensation) was developed for the rapid synthesis of thiophene‐based organic dyes for dye‐sensitized solar cells (DSSCs). Seven thiophene‐based, organic dyes of various donor structures with/without the use of a 3,4‐ethylenedioxythiophene (EDOT) moiety were successfully synthesized in good yields based on a readily available thiophene boronic acid pinacol ester scaffold (one‐pot, 3‐step, 35–61 %). Evaluation of the photovoltaic properties of the solar cells that were prepared using the synthesized dyes revealed that the introduction of an EDOT structure beside a cyanoacrylic acid moiety improved the short‐circuit current (Jsc) while decreasing the fill factor (FF). The donor structure significantly influenced the open‐circuit voltage (Voc), the FF, and the power conversion efficiency (PCE). The use of a n‐hexyloxyphenyl amine donor, and our originally developed, rigid, and nonplanar donor, both promoted good cell performance (η=5.2–5.6 %). |
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| Keywords: | C H activation cross‐coupling dyes/pigments dye‐sensitized solar cells one‐pot reactions |
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