Citation: Hao Heng, Pengyu Xu, Zhaobin Wang, Xianhe Ou, Jiajin Chen, Yu Chen, Yuning Xia, Fude Feng. Photoactivatable in-cell synthesis of near infrared trimethine cyanines using benzo[cd]indolium derivatives for imaging mitochondria[J]. Chinese Chemical Letters, ;2026, 37(12): 112316. doi: 10.1016/j.cclet.2025.112316 shu

Photoactivatable in-cell synthesis of near infrared trimethine cyanines using benzo[cd]indolium derivatives for imaging mitochondria

Hao Heng ^{a, 1,*,} ,
Pengyu Xu ^{a, 1} ,
Zhaobin Wang ^{b, 1} ,
Xianhe Ou ^a ,
Jiajin Chen ^a ,
Yu Chen ^c ,
Yuning Xia ^d ,
Fude Feng ^{b, *,}

a.
School of Pharmacy, Key Laboratory of Anti-inflammatory and Immune Medicine, Ministry of Education, Institute of Clinical Pharmacology, Anhui Medical University, Hefei 230032, China
b.
MOE Key Laboratory of High Performance Polymer Materials and Technology, Department of Polymer Science & Engineering, School of Chemistry & Chemical Engineering, Nanjing University, Nanjing 210023, China
c.
Second Clinical Medical College, Anhui Medical University, Hefei 230032, China
d.
First Clinical Medical College, Anhui Medical University, Hefei 230032, China

henghao@ahmu.edu.cn

fengfd@nju.edu.cn

Received Date: 18 October 2025
Revised Date: 22 December 2025
Accepted Date: 22 December 2025
Available Online: 23 December 2025

Figures(7)

Traditional trimethine cyanines (Cy3) dyes with the emission wavelength range of 550–700 nm face multiple limitations in practical applications. Herein, we propose a photoactivation strategy to make benzo[cd]indolium-containing Cy3, which exhibit favorable fluorescence in the near infrared (NIR) region (750–1200 nm). The eco-friendly synthetic method demonstrates excellent air tolerance while requiring no photosensitizers, metals, or condensation agents. Computational results indicate that the synthesized cyanines exhibit a highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) energy bandgap between 2.029 eV and 2.063 eV, and the pure functional BP86 shows relatively small errors in predicting the maximum absorption wavelength. Besides, the synthesized Cy3 dyes display comparable photophysical characteristics to indocyanine green (ICG) while demonstrating improved photostability. Moreover, using benzo[cd]indolium derivatives as the sole exogenous precursor, the NIR Cy3 dyes were in situ synthesized in living cells using the photoactivation method, demonstrating significant potential for spatiotemporally controlled mitochondria-specific imaging.
- In-cell synthesis,
- Photoactivation,
- Trimethine cyanines,
- Near infrared imaging,
- Mitochondria
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