Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 49, Pages 13548-13552Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407670
Keywords
anions; electrochemistry; host-guest systems; macrocycles; structure elucidation
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Funding
- National Natural Science Function of China [21132005, 21121004]
- Ministry of Science and Technology of China [2011CB932501]
- Tsinghua University
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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.
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