Planarized B,N-phenylated dibenzoazaborine with a carbazole substructure: electronic impact of the structural constraint

Mikinori Ando; Mika Sakai; Naoki Ando; Masato Hirai; Shigehiro Yamaguchi

doi:10.1039/C9OB00934E

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Planarized B,N-phenylated dibenzoazaborine with a carbazole substructure: electronic impact of the structural constraint†

Mikinori Ando,^a Mika Sakai,^a Naoki Ando,

^a Masato Hirai^c and Shigehiro Yamaguchi

*^abc

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* Corresponding authors

^a Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya, Japan

^b Integrated Research Consortium on Chemical Sciences (IRCCS), Nagoya University, Furo, Chikusa, Nagoya, Japan

^c Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo, Chikusa, Nagoya, Japan
E-mail: yamaguchi@chem.nagoya-u.ac.jp

Abstract

A B,N-diphenyl-5,10-dihydro-dibenzo-1,4-azaborine, in which both phenyl groups on the boron and nitrogen atoms are planarized to generate a carbazole substructure, was synthesized. The structral constraint around the boron and nitrogen atoms alters the π-conjugation mode and thus the photophysical and electrochemical properties. Specifically, this structurally constrained dibenzoazaborine showed an intense blue emission with a narrow full width at half maximum. One of its derivatives exhibited near infrared absorption in the one-electron-oxidized state.

This article is part of the themed collection: Trends in Organoboron Chemistry

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DOI: https://doi.org/10.1039/C9OB00934E
Article type: Communication
Submitted: 24 Apr 2019
Accepted: 14 May 2019
First published: 14 May 2019

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Org. Biomol. Chem., 2019,17, 5500-5504

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Planarized B,N-phenylated dibenzoazaborine with a carbazole substructure: electronic impact of the structural constraint

M. Ando, M. Sakai, N. Ando, M. Hirai and S. Yamaguchi, Org. Biomol. Chem., 2019, 17, 5500 DOI: 10.1039/C9OB00934E

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Organic & Biomolecular Chemistry

Planarized B,N-phenylated dibenzoazaborine with a carbazole substructure: electronic impact of the structural constraint†

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Planarized B,N-phenylated dibenzoazaborine with a carbazole substructure: electronic impact of the structural constraint

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