Molecularly engineered AIEgens with enhanced quantum and singlet-oxygen yield for mitochondria-targeted imaging and photodynamic therapy

Fang Zhou Xu, Ling Zhu, Hai Hao Han, Jian Wei Zou, Yi Zang, Jia Li, Tony D. James, Xiao Peng He, Cheng Yun Wang

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11 Citations (SciVal)

Abstract

Luminogens characteristic of aggregation-induced emission (AIEgens) have been extensively exploited for the development of imaging-guided photodynamic therapeutic (PDT) agents. However, intramolecular rotation of donor-acceptor (D-A) type AIEgens favors non-radiative decay of photonic energy which results in unsatisfactory fluorescence quantum and singlet oxygen yields. To address this issue, we developed several molecularly engineered AIEgens with partially “locked” molecular structures enhancing both fluorescence emission and the production of triplet excitons. A triphenylphosphine group was introduced to form a D-A conjugate, improving water solubility and the capacity for mitochondrial localization of the resulting probes. Experimental and theoretical analyses suggest that the much higher quantum and singlet oxygen yield of a structurally “significantly-locked” probe (LOCK-2) than its “partially locked” (LOCK-1) and “unlocked” equivalent (LOCK-0) is a result of suppressed AIE and twisted intramolecular charge transfer. LOCK-2 was also used for the mitochondrial-targeting, fluorescence image-guided PDT of liver cancer cells.

Original languageEnglish
Pages (from-to)9373-9380
JournalChemical Science
Volume13
Issue number32
Early online date3 Aug 2022
DOIs
Publication statusPublished - 28 Aug 2022

Bibliographical note

Funding Information:
X.-P. H. thanks the National Natural Science Foundation of China (No. 21788102, 91853201) and the Shanghai Science and Technology Committee (No. 19410712600). C.-Y. W. is grateful for financial support from Natural Science Foundation of Shanghai (No. 22ZR1417300). H.-H. H. thanks the National Natural Science Foundation of China (No. 22107029) and Project funded by China Postdoctoral Science Foundation (No. 2020M681196). T. D. J. wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01).

ASJC Scopus subject areas

  • General Chemistry

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