Issue 17, 2024

Planar-structured thiadiazoloquinoxaline-based NIR-II dye for tumor phototheranostics

Abstract

Second near-infrared (NIR-II) fluorescence imaging shows huge application prospects in clinical disease diagnosis and surgical navigation, while it is still a big challenge to exploit high performance NIR-II dyes with long-wavelength absorption and high fluorescence quantum yield. Herein, based on planar π-conjugated donor–acceptor–donor systems, three NIR-II dyes (TP-DBBT, TP-TQ1, and TP-TQ2) were synthesized with bulk steric hindrance, and the influence of acceptor engineering on absorption/emission wavelengths, fluorescence efficiency and photothermal properties was systematically investigated. Compared with TP-DBBT and TP-TQ2, the TP-TQ1 based on 6,7-diphenyl-[1,2,5]thiadiazoloquinoxaline can well balance absorption/emission wavelengths, NIR-II fluorescence brightness and photothermal effects. And the TP-TQ1 nanoparticles (NPs) possess high absorption ability at a peak absorption of 877 nm, with a high relative quantum yield of 0.69% for large steric hindrance hampering the close π–π stacking interactions. Furthermore, the TP-TQ1 NPs show a desirable photothermal conversion efficiency of 48% and good compatibility. In vivo experiments demonstrate that the TP-TQ1 NPs can serve as a versatile theranostic agent for NIR-II fluorescence/photoacoustic imaging-guided tumor phototherapy. The molecular planarization strategy provides an approach for designing efficient NIR-II fluorophores with extending absorption/emission wavelength, high fluorescence brightness, and outstanding phototheranostic performance.

Graphical abstract: Planar-structured thiadiazoloquinoxaline-based NIR-II dye for tumor phototheranostics

Supplementary files

Article information

Article type
Paper
Submitted
14 Feb 2024
Accepted
27 Mar 2024
First published
29 Mar 2024

J. Mater. Chem. B, 2024,12, 4197-4207

Planar-structured thiadiazoloquinoxaline-based NIR-II dye for tumor phototheranostics

L. Zheng, Z. Zhao, C. Xue, L. An, W. Na, F. Gao, J. Shao and C. Ou, J. Mater. Chem. B, 2024, 12, 4197 DOI: 10.1039/D4TB00302K

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