A general near-infrared fluorescence analysis platform via N-substituent modulation of tricyclic boronic ester hemicyanine dyes.

Authors

Ruyu Yan, Yuetian Li, Zhenming Hao, Keke Yao, You Zhou, Liming Hu, Shanyan Mo

Published in

Analytica chimica acta. Volume 1421. Pages 346011. Nov 01, 2026. Epub Jul 23, 2026.

Abstract

Conventional responsive fluorescent probes often suffer from high background signals, laborious multi-step synthesis, and limited photophysical tunability, which constrain their practical applications in biosensing. Developing a generalizable platform that integrates facile synthesis, efficient quenching, and modular target responsiveness is urgently needed. Herein, we address this challenge by exploring N-substituent electronic modulation on tricyclic boronic ester hemicyanine (TBEH) dyes as a unified strategy for constructing high-performance turn-on NIR probes.
Through N-substituent engineering, electron-withdrawing groups (EWGs) effectively quench fluorescence via a photoinduced electron transfer (PET) mechanism, while analyte-triggered conversion to electron-donating species or elimination restores emission. Three probes were developed for hypoxia (2d), glutathione (2f), and bioorthogonal (2g) detection, exhibiting 130-, 54-, and 13-fold fluorescence turn-on with detection limits of 16, 90, and 33 nM, respectively. All probes showed rapid response (20-40 min), excellent selectivity, and good biocompatibility in live-cell imaging. DFT calculations confirmed that EWGs lower acceptor LUMO energies to enable PET quenching, and target interactions reverse this process to recover fluorescence.
This work establishes a universal TBEH-based fluorescence analysis platform that combines synthetic simplicity, electronically tunable photophysical properties, and high sensitivity. The N-substituent modulation strategy offers a straightforward blueprint for developing diverse responsive NIR probes for real-time biosensing and theranostic applications.

PMID:
42702442
Bibliographic data and abstract were imported from PubMed on 07 Sep 2026.

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