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Issue 33, 2019
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Near-infrared fluorescein dyes containing a tricoordinate boron atom

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Abstract

Bora-fluoresceins (BFs), fluorescein analogues containing a tricoordinate boron atom instead of an oxygen atom at the 10-position of the fluorescein skeleton, were synthesized as a new family of fluorescein analogues. The deprotonated BFs exhibited absorption and fluorescence in the near-infrared region, which were significantly red-shifted relative to those of hitherto-known heteroatom-substituted fluorescein analogues on account of the orbital interaction between the tricoordinate boron atom and the fluorescein skeleton. BFs also showed multi-stage changes resulting from a Lewis acid–base equilibrium at the boron center in combination with a Brønsted acid–base equilibrium at the phenolic hydroxy group.

Graphical abstract: Near-infrared fluorescein dyes containing a tricoordinate boron atom

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Supplementary files

Article information


Submitted
11 May 2019
Accepted
03 Jul 2019
First published
03 Jul 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 7816-7821
Article type
Edge Article

Near-infrared fluorescein dyes containing a tricoordinate boron atom

N. Ando, H. Soutome and S. Yamaguchi, Chem. Sci., 2019, 10, 7816
DOI: 10.1039/C9SC02314C

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