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.
引用
收藏
页码:16974 / 16979
页数:6
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