Design, synthesis, and biological application of A–D–A-type boranil fluorescent dyes

Abstract

For the first time, three acceptor–donor–acceptor (A–D–A)-type boranil fluorescent dyes, CSU-BF-R (R = H, CH3, and OCH3), featuring phenothiazine as the donor, were designed and synthesized. CSU-BF-R exhibited remarkable photophysical characteristics, including large Stokes shifts (>150 nm), high fluorescence quantum yields (up to 40%), long-wavelength emissions, and strong red solid-state fluorescence. Moreover, these CSU-BF-R fluorescent dyes were demonstrated to function as highly selective and sensitive ratiometric fluorescent probes for detecting hypochlorous acid (HClO). The preliminary biological applications of CSU-BF-OCH3 for sensing intracellular HClO in living cells and zebrafish were demonstrated. Therefore, CSU-BF-R possess the potential to further explore the physiological and pathological functions associated with HClO and provide valuable insights into the design of high-performance A–D–A-type fluorescent dyes.

Graphical abstract: Design, synthesis, and biological application of A–D–A-type boranil fluorescent dyes

Supplementary files

Article information

Article type
Paper
Submitted
24 Feb 2024
Accepted
16 Apr 2024
First published
16 Apr 2024

Org. Biomol. Chem., 2024, Advance Article

Design, synthesis, and biological application of A–D–A-type boranil fluorescent dyes

W. Luo, Y. Li, L. Wang, Y. Qin, Q. Cheng, G. Hu, C. Yao and X. Song, Org. Biomol. Chem., 2024, Advance Article , DOI: 10.1039/D4OB00297K

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