title: Rapid Synthesis of Thiophene-Based, Organic Dyes for Dye-Sensitized Solar Cells (DSSCs) by a One-Pot, Four-Component Coupling Approach.
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%).
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552 (Japan).
authors.forename: Keisuke
authors.initials: K
authors.lastname: Matsumura
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552 (Japan).
authors.forename: Soichi
authors.initials: S
authors.lastname: Yoshizaki
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552 (Japan).
authors.forename: Masato M
authors.initials: MM
authors.lastname: Maitani
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552 (Japan).
authors.forename: Yuji
authors.initials: Y
authors.lastname: Wada
authors.affiliation: Graduate School of Life Science and Systems Engineering, Kyusyu Institute of Technology, Fukuoka 808-0196 (Japan).
authors.forename: Yuhei
authors.initials: Y
authors.lastname: Ogomi
authors.affiliation: Graduate School of Life Science and Systems Engineering, Kyusyu Institute of Technology, Fukuoka 808-0196 (Japan).
authors.forename: Shuzi
authors.initials: S
authors.lastname: Hayase
authors.affiliation: Kanto Natural Gas Development Co., Ltd. Brine Resources Research & Development Division, Chiba 297-8550 (Japan).
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Kaiho
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552 (Japan). sfuse@res.titech.ac.jp.|Present address: Chemical Resources Laboratory, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503 (Japan). sfuse@res.titech.ac.jp.
authors.forename: Shinichiro
authors.initials: S
authors.lastname: Fuse
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552 (Japan).
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tanaka
authors.affiliation: Yokohama College of Pharmacy, 601, Matano-cho, Totsuka-ku, Yokohama 245-0066 (Japan).
authors.forename: Takashi
authors.initials: T
authors.lastname: Takahashi
keywords: CH activation; cross-coupling; dye-sensitized solar cells; dyes/pigments; one-pot reactions