Ultra-photostable small-molecule dyes facilitate near-infrared biophotonics

Kui Yan, Zhubin Hu, Peng Yu, Zuyang He, Ying Chen, Jiajian Chen, Haitao Sun (), Shangfeng Wang () and Fan Zhang ()
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Kui Yan: Fudan University
Zhubin Hu: East China Normal University
Peng Yu: Fudan University
Zuyang He: Fudan University
Ying Chen: Fudan University
Jiajian Chen: Fudan University Shanghai Cancer Center
Haitao Sun: East China Normal University
Shangfeng Wang: Fudan University
Fan Zhang: Fudan University

Nature Communications, 2024, vol. 15, issue 1, 1-14

Abstract: Abstract Long-wavelength, near-infrared small-molecule dyes are attractive in biophotonics. Conventionally, they rely on expanded aromatic structures for redshift, which comes at the cost of application performance such as photostability, cell permeability, and functionality. Here, we report a ground-state antiaromatic strategy and showcase the concise synthesis of 14 cationic aminofluorene dyes with mini structures (molecular weights: 299–504 Da) and distinct spectra covering 700–1600 nm. Aminofluorene dyes are cell-permeable and achieve rapid renal clearance via a simple 44 Da carboxylation. This accelerates optical diagnostics of renal injury by 50 min compared to existing macromolecular approaches. We develop a compact molecular sensing platform for in vivo intracellular sensing, and demonstrate the versatile applications of these dyes in multispectral fluorescence and optoacoustic imaging. We find that aromaticity reversal upon electronic excitation, as indicated by magnetic descriptors, not only reduces the energy bandgap but also induces strong vibronic coupling, resulting in ultrafast excited-state dynamics and unparalleled photostability. These results support the argument for ground-state antiaromaticity as a useful design rule of dye development, enabling performances essential for modern biophotonics.

Date: 2024
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DOI: 10.1038/s41467-024-46853-0

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