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Ionization and Anion-π+ Interaction: A New Strategy for Structural Design of Aggregation-Induced Emission Luminogens
被引:226
作者:
Wang, Jianguo
[1
,5
]
Gu, Xinggui
[1
]
Zhang, Pengfei
[1
]
Huang, Xiaobo
Zheng, Xiaoyan
[1
,2
]
Chen, Ming
[1
]
Feng, Haitao
[1
]
Kwok, Ryan T. K.
[1
]
Lam, Jacky W. Y.
[1
]
Tang, Ben Zhong
[1
,3
,4
]
机构:
[1] Hong Kong Univ Sci & Technol, Dept Chem,Div Life Sci & Biomed Engn, Hong Kong Branch Chinese Natl Engn,State Key Lab, Res Ctr Tissue Restorat & Reconstruct,Inst Mol Fu, Kowloon, Hong Kong, Peoples R China
[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
[3] South China Univ Technol, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China
[4] HKUST Shenzhen Res Inst, Guangdong Prov Key Lab Brain Sci Dis & Drug Dev, Shenzhen 518057, Peoples R China
[5] Gannan Normal Univ, Key Lab Organo Pharmaceut Chem, Ganzhou 341000, Peoples R China
基金:
中国国家自然科学基金;
关键词:
ANION-PI INTERACTIONS;
INTRAMOLECULAR CHARGE-TRANSFER;
NONCOVALENT INTERACTIONS;
SUPRAMOLECULAR POLYMER;
CANCER-CELLS;
SOLID-STATE;
RECOGNITION;
COMPLEXES;
BIOPROBE;
BINDING;
D O I:
10.1021/jacs.7b10150
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
Recent years have witnessed the significant role of anion-pi(+) interactions in many areas, which potentially brings the opportunity for the development of aggregation-induced emission (AIE) systems. Here, a new strategy that utilized anion-pi(+) interactions to block detrimental pi-pi stacking was first proposed to develop inherent-charged AIE systems. Two AIE-active luminogens, namely, 1,2,3,4-tetraphenyloxazolium (TPO-P) and 2,3,5-triphenyloxazolium (TriPO-PN), were successfully synthesized. Comprehensive techniques such as single-crystal analysis, theoretical calculation, and conductivity measurement were used to illustrate the effects of anion-pi(+) interactions on the AIE feature. Their analogues tetraphenylfuran (TPF) and 2,4,5-triphenyloxazole (TriPO-C) without anion-pi(+) interactions suffered from the aggregation-caused emission quenching in the aggregate state, demonstrating the important role of anion-pi(+) interactions in suppressing pi-pi stacking. TriPO-PN was biocompatible and could specifically target lysosome in fluorescence turn-on and wash-free manners. This suggested that it was a promising contrast agent for bioimaging.
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页码:16974 / 16979
页数:6
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