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A Green Fluorescent Nitrogen‐Doped Aromatic Belt Containing a [6]Cycloparaphenylene Skeleton
Author(s) -
Zhang Fan,
Du XuSheng,
Zhang DaWei,
Wang YinFeng,
Lu HaiYan,
Chen ChuanFeng
Publication year - 2021
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.202104259
Subject(s) - conjugated system , carbazole , homo/lumo , fluorescence , nitrogen , supramolecular chemistry , aromaticity , photochemistry , quantum yield , doping , chemistry , materials science , organic chemistry , crystal structure , polymer , molecule , optoelectronics , physics , quantum mechanics
The design and synthesis of nitrogen‐doped aromatic belts with conjugated structures still remain a challenge. Here, we report the first nitrogen‐doped aromatic belt with a [6]cycloparaphenylene skeleton, which is conveniently synthesized from the easily available calix[3]carbazole. The aromatic belt has a rigid conjugated structure and deep cavity, and it can encapsulate one dichloromethane both in solution and in the solid state. Interestingly, the aromatic belt shows strong green fluorescence with a quantum yield of 0.39 and exhibits a narrow HOMO–LUMO energy gap of 2.02 eV. The belt‐shaped conjugated structure composed of three carbazole subunits has specific optoelectronic properties that will promote wide applications in supramolecular chemistry and materials science.