Anion‐Responsive Colorimetric and Fluorometric Red‐Shift in Triarylborane Derivatives: Dual Role of Phenazaborine as Lewis Acid and Electron Donor

Author:

Aota Nae1ORCID,Nakagawa Riku1,de Sousa Leonardo Evaristo2ORCID,Tohnai Norimitsu1ORCID,Minakata Satoshi1ORCID,de Silva Piotr2ORCID,Takeda Youhei1ORCID

Affiliation:

1. Department of Applied Chemistry Graduate School of Engineering Osaka University Yamadaoka 2-1 Suita Osaka 565-0871 Japan

2. Department of Energy Conversion and Storage Technical University of Denmark Anker Engelunds Vej 301 2800 Kongens Lyngby Denmark

Abstract

AbstractPhotophysical modulation of triarylboranes (TABs) through Lewis acid‐base interactions is a fundamental approach for sensing anions. Yet, design principles for anion‐responsive TABs displaying significant red‐shift in absorption and photoluminescence (PL) have remained elusive. Herein, a new strategy for modulating the photophysical properties of TABs in a red‐shift mode has been presented, by using a nitrogen‐bridged triarylborane (1,4‐phenazaborine: PAzB) with a contradictory dual role as a Lewis acid and an electron donor. Following the strategy, PAzB derivatives connected with an electron‐deficient azaaromatic have been developed, and these compounds display a distinct red‐shift in their absorption and PL in response to an anion. Spectroscopic analyses and quantum chemical calculations have revealed the formation of a tetracoordinate borate upon the addition of fluoride, narrowing the HOMO–LUMO gap and enhancing the charge‐transfer character in the excited state. This approach has also been demonstrated in modulating the photophysical properties of solid‐state films.

Funder

Japan Society for the Promotion of Science

Danmarks Frie Forskningsfond

Publisher

Wiley

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