Synthesis, Structure, and Properties of O-6-Corona[3] arene[3]tetrazines

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...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 53; no. 49; pp. 13548 - 13552
Main Authors Guo, Qing-Hui, Fu, Zhan-Da, Zhao, Liang, Wang, Mei-Xiang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.12.2014
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
host-guest systems
electrochemistry
RECOGNITION
macrocycles
PI INTERACTIONS
structure elucidation
anions
MOLECULES
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201407670