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Synthesis, Structure, and Properties of O 6 ‐Corona[3]arene[3]tetrazines
Author(s) -
Guo QingHui,
Fu ZhanDa,
Zhao Liang,
Wang MeiXiang
Publication year - 2014
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.201407670
Subject(s) - acetonitrile , chemistry , differential pulse voltammetry , tetrazine , cyclic voltammetry , steric effects , crystallography , aromaticity , nucleophilic aromatic substitution , cyclophane , nucleophilic substitution , phenylene , photochemistry , crystal structure , stereochemistry , molecule , medicinal chemistry , electrochemistry , organic chemistry , electrode , polymer
O 6 ‐Corona[3]arene[3]tetraazines, a new class of macrocyclic compounds, were synthesized efficiently in a one‐pot reaction from the nucleophilic aromatic substitution reaction between 1,4‐dihydroxybenzene derivatives and 3,6‐dichlorotetrazine in warm acetonitrile. In the crystalline structure, the resulting macrocycles adopt highly symmetric structures of a regular hexagonal cavity with all bridging oxygen atoms and tetrazine rings located on the same plane with phenylene units orthogonally orientated. The constitutional aromatic rings are able to rotate around the macrocyclic annulus, depending on the steric effect of the substituents and temperature, in solution. The electron‐deficient nature revealed by cyclic voltammetry, differential pulse voltammetry, and characteristic absorbances at a visible region show the O 6 ‐corona[3]arene[3]tetrazines to be suitable macrocyclic receptors for electron‐rich guests.