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Planar AIEgens with Enhanced Solid‐State Luminescence and ROS Generation for Multidrug‐Resistant Bacteria Treatment
Author(s) -
Ni JenShyang,
Min Tianliang,
Li Yaxi,
Zha Menglei,
Zhang Pengfei,
Ho Chun Loong,
Li Kai
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202001103
Subject(s) - stacking , intermolecular force , triphenylamine , tetraphenylethylene , chemistry , photochemistry , substituent , aggregation induced emission , quenching (fluorescence) , double bond , excited state , fluorescence , molecule , stereochemistry , organic chemistry , physics , quantum mechanics , nuclear physics
Planar luminogens have encountered difficulties in overcoming intrinsic aggregation‐caused emission quenching by intermolecular π‐π stacking interactions. Although excited‐state double‐bond reorganization (ESDBR) can guide us on designing planar aggregation‐induced emission (AIE) luminogens (AIEgens), its mechanism has yet been elucidated. Major challenges in the field include methods to efficiently restrict ESDBR and enhance AIE performance without using bulky substituents (e.g., tetraphenylethylene and triphenylamine). In this study, we rationally developed fluoro‐substituent AIEgens with stronger intermolecular H‐bonding interaction for restricted molecular motions and increased crystal density, leading to decreased nonradiative decay rate by one order of magnitude. The adjusted ESDBR properties also show a corresponding response to variation in viscosity. Furthermore, their aggregation‐induced reactive oxygen species (ROS) generations have been discovered. The application of such planar AIEgen in treating multidrug‐resistant bacteria has been demonstrated in a mouse model. The relationship between ROS generation and distinct E / Z ‐configurational stacking behaviors have been further understood, providing a design principle for synthesizing planar AIEgen‐based photosensitizers.