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Updated: Jan 6, 2026

A Bright NIR-II Fluorescence Probe for Vascular and Tumor Imaging
Published on: March 17, 2023
Near-infrared fluorescein dyes containing a tricoordinate boron atom
Naoki Ando1, Hiroki Soutome1, Shigehiro Yamaguchi1,2
1Department of Chemistry , Graduate School of Science , Integrated Research Consortium on Chemical Sciences (IRCCS) , Nagoya University , Furo, Chikusa , Nagoya 464-8602 , Japan .
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.
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