Lewis-Pairing-Induced Electrochemiluminescence Enhancement from Electron Donor-Acceptor Diads Decorated with Tris(pentafluorophenyl)borane as an Electrochemical Protector |
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| Authors: | Takashi Ikeda Dr. Keishiro Tahara Dr. Ryoichi Ishimatsu Prof. Toshikazu Ono Dr. Luxia Cui Momoka Maeda Prof. Yoshiki Ozawa Prof. Masaaki Abe |
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| Affiliation: | 1. Department of Material Science, Graduate School of Science, University of Hyogo, 3-2-1, Kouto, Kamigori, Ako, Hyogo, 678-1297 Japan;2. Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395 Japan;3. Department of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395 Japan |
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| Abstract: | This study reports an effective peripheral decoration of organic donor-acceptor diads with B(C6F5)3 for stabilizing electrogenerated radical ions. By employing a common p-type organic semiconductor benzothienobenzothiophene (BTBT) as the donor, tetracoordinate boron complexes showed improved solution electrochemiluminescence (ECL) intensity, reaching a 156-fold increase compared to that of the parent diad. The unprecedented Lewis-pairing-induced ECL enhancement is attributed to the multiple roles of B(C6F5)3: 1) redistributing frontier orbitals, 2) facilitating electrochemical excitation, and 3) restricting molecular motions. Furthermore, B(C6F5)3 converted the molecular arrangement of BTBT from conventional 2D herringbones into 1D π-stacks. This robust, highly ordered columnar nanostructure allowed red-shifting of the crystalline film ECL with electrochemical doping through the electronic coupling pathways of BTBT. Our approach will facilitate the development of elaborate metal-free ECL systems. |
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| Keywords: | Conjugation Donor-Acceptor Systems Electrochemistry Lewis Acid Supramolecular Chemistry |
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