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BowtieArene: A Dual Macrocycle Exhibiting Stimuli‐Responsive Fluorescence
Author(s) -
Lei ShengNan,
Xiao Hongyan,
Zeng Yi,
Tung ChenHo,
Wu LiZhu,
Cong Huan
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913340
Subject(s) - tetraphenylethylene , fluorophore , pillar , fluorescence , supramolecular chemistry , molecule , absorption (acoustics) , nanotechnology , solvent polarity , dual (grammatical number) , materials science , chemistry , photochemistry , aggregation induced emission , optics , organic chemistry , physics , structural engineering , composite material , engineering , art , literature
Although highly useful in supramolecular chemistry, pillararenes lack a fluorophore in their skeleton. Here we present BowtieArene, a novel fluorescent dual macrocycle, featuring a central tetraphenylethylene‐derived fluorophore and two pillar‐like, pentagon‐shaped cavities which are comparable to pillar[5]arene. This concisely prepared, figure‐of‐eight molecule exhibits vapor absorption and host–guest capabilities, as well as intriguing switchable fluorescence. The fluorochromism of BowtieArene can be triggered by multiple external stimuli including solvent, vapor, and mechanical force, with excellent reversibility and stability. Experimental and theoretical evidence indicate that the fluorochromism should be closely related to molecular packing.