Photodissociative Modules that Control Dual‐Emission Properties in Donor–π–Acceptor Organoborane Fluorophores

Author:

Kawashiro Midori1,Mori Tatsuya1ORCID,Ito Masato1,Ando Naoki1ORCID,Yamaguchi Shigehiro12ORCID

Affiliation:

1. Department of Chemistry, Graduate School of Science and Integrated Research Consortium on Chemical Sciences (IRCCS) Nagoya University Furo, Chikusa Nagoya 464-8602 Japan

2. Institute of Transformative Bio-Molecules (WPI-ITbM) Nagoya University Furo, Chikusa Nagoya 464-8601 Japan

Abstract

AbstractDonor–π–acceptor fluorophores that consist of an electron‐donating amino group and an electron‐accepting triarylborane moiety generally exhibit substantial solvatochromism in their fluorescence while retaining high fluorescence quantum yields even in polar media. Herein, we report a new family of this compound class, which bears ortho‐P(=X)R2‐substituted phenyl groups (X=O or S) as a photodissociative module. The P=X moiety that intramolecularly coordinates to the boron atom undergoes dissociation in the excited state, giving rise to dual emission from the corresponding tetra‐ and tricoordinate boron species. The susceptibility of the systems to photodissociation depends on the coordination ability of the P=O and P=S moieties, whereby the latter facilitates dissociation. The intensity ratios of the dual emission bands are sensitive to environmental parameters, including temperature, solution polarity, and the viscosity of the medium. Moreover, precise tuning of the P(=X)R2 group and the electron‐donating amino moiety led to single‐molecule white emission in solution.

Funder

Japan Society for the Promotion of Science

Core Research for Evolutional Science and Technology

Publisher

Wiley

Subject

General Medicine

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