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Natural Coumarin Isomers with Dramatically Different AIE Properties: Mechanism and Application
Chen,Shan-Shan; Wang,Haoran; Wu,Bo; Li,Qiyao; Gong,Junyi; Zhao,Yun-Li; Zhao,Yun; Xiao,Xia; Lam,Jacky W. Y.; Zhao,Zheng; Luo,Xiao-Dong; Tang,Ben Zhong
2023
Source PublicationACS CENTRAL SCIENCE
ISSN2374-7951
Volume9Issue:5Pages:883-891
AbstractAggregation-induced emission luminogens (AIEgens) are of great importance in optoelectronics and biomedical fields. However, the popular design philosophy by combining rotors with traditional fluorophores limits the imagination and structural diversity of AIEgens. Inspired by the fluorescent roots of the medicinal plant Toddalia asiatica, we discovered two unconventional rotor-free AIEgens, 5-methoxyseselin (5-MOS) and 6-methoxyseselin (6-MOS). Interestingly, a slight structural difference of the coumarin isomers leads to completely contrary fluorescent properties upon aggregation in aqueous media. Further mechanism investigation indicates that 5-MOS forms different extents of aggregates with the assistance of protonic solvents, leading to electron/energy transfer, which is responsible for its unique AIE feature, i.e., reduced emission in aqueous media but enhanced emission in crystal. Meanwhile, for 6-MOS, the conventional restriction of the intramolecular motion (RIM) mechanism is responsible for its AIE feature. More interestingly, the unique water-sensitive fluorescence property of 5-MOS enables its successful application for wash-free mitochondria imaging. This work not only demonstrates an ingenious tactic to seek new AIEgens from natural fluorescent species but also benefits the structure design and application exploration of next-generation AIEgens.
KeywordAGGREGATION-INDUCED EMISSION AIEGENS ABSORPTION CHEMISTRY
Subject AreaChemistry
DOI10.1021/acscentsci.3c00012
WOS IDWOS:000975408700001
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Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/74861
Collection中国科学院昆明植物研究所
Recommended Citation
GB/T 7714
Chen,Shan-Shan,Wang,Haoran,Wu,Bo,et al. Natural Coumarin Isomers with Dramatically Different AIE Properties: Mechanism and Application[J]. ACS CENTRAL SCIENCE,2023,9(5):883-891.
APA Chen,Shan-Shan.,Wang,Haoran.,Wu,Bo.,Li,Qiyao.,Gong,Junyi.,...&Tang,Ben Zhong.(2023).Natural Coumarin Isomers with Dramatically Different AIE Properties: Mechanism and Application.ACS CENTRAL SCIENCE,9(5),883-891.
MLA Chen,Shan-Shan,et al."Natural Coumarin Isomers with Dramatically Different AIE Properties: Mechanism and Application".ACS CENTRAL SCIENCE 9.5(2023):883-891.
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