Issue 18, 2024

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., 2024,22, 3725-3731

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, 22, 3725 DOI: 10.1039/D4OB00297K

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