N, O - Chelate Fluoroborane Dyes: Synthesis, Optical Properties in Dual Aggregate State.

Authors

Yangyang Liu, Debao Liu, Nuonuo Zhang, Jiaying Yan

Published in

Journal of fluorescence. Apr 23, 2025. Epub Apr 23, 2025.

Abstract

In this work, two novel N, O - chelate fluoroborane fluorescent dyes TN-1 and TN-2 with different substituents on indanone unit were synthesized via condensation reaction from indanone derivatives and benzo[cd]indol-2(1H)-one followed by fluorine-boron coordination reaction. To increase the solubility of dyes, TN-2-H and TN-2-M were designed and synthesized by another condensation reaction on active site of indanone unit on TN-2 with benzaldehyde derivatives. The optical properties of these compounds in different solvents and solid state were discussed. The maximum fluorescence emission wavelength is 654 nm with a fluorescence quantum yield (FQY) of 12% in toluene and the maximum solid fluorescence emission wavelength reaches 737 nm with an FQY of 3.15%. All the compounds were characterized by NMR, HRMS, UV-Vis absorption and fluorescence emission spectroscopy. TN-2-M was further characterized by single crystal diffraction analysis, and DFT calculations were used for modeling structure and spectra. It provide a theoretical basis for the design of near - infrared (NIR) dual - effect fluorescent dyes.

PMID:
40266480
Bibliographic data and abstract were imported from PubMed on 23 Apr 2025.

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