Lewis‐Pairing‐Induced Electrochemiluminescence Enhancement from Electron Donor‐Acceptor Diads Decorated with Tris(pentafluorophenyl)borane as an Electrochemical Protector

Author:

Ikeda Takashi1,Tahara Keishiro12ORCID,Ishimatsu Ryoichi3ORCID,Ono Toshikazu4ORCID,Cui Luxia4ORCID,Maeda Momoka4,Ozawa Yoshiki1ORCID,Abe Masaaki1ORCID

Affiliation:

1. Department of Material Science Graduate School of Science University of Hyogo 3-2-1, Kouto Kamigori, Ako, Hyogo 678-1297 Japan

2. Present address: Faculty of Engineering and Design Kagawa University 2217-20 Hayashi-cho Takamatsu, Kagawa 761-0396 Japan

3. Department of Applied Chemistry, Graduate School of Engineering Kyushu University 744 Motooka Nishi-ku, Fukuoka 819-0395 Japan

4. Department of Chemistry and Biochemistry Graduate School of Engineering Center for Molecular Systems (CMS) Kyushu University 744 Motooka Nishi-ku, Fukuoka 819-0395 Japan

Abstract

AbstractThis 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.

Publisher

Wiley

Subject

General Medicine

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