Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 25, Pages 7151-7155Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703008
Keywords
corona[5]arenes; electrochemistry; electronic spectra; macrocycle-to-macrocycle transformations; three-component reactions
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Funding
- National Natural Science Function of China [21132005, 91427301, 21421064]
- Tsinghua University
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Corona[5]arenes, a novel type of macrocyclic compound that is composed of alternating heteroatoms and para-arylenes, were synthesized efficiently by two distinct methods. In a macrocycle-to-macrocycle transformation approach, S-6-corona[3]arene[3]tetrazine underwent sequential SNAr reactions with HS-C6H4-X-C6H4-SH (X = S, CH2, CMe2, SO2, and O) to produce the corresponding corona[3]arene[2]tetrazines. Different corona[3]arene[2]tetrazine compounds were also constructed in a straightforward manner by a one-pot three-component reaction of HS-C6H4-X-C6H4-SH (X = S, CH2, CMe2, SO2, and O) with diethyl 2,5-dimercaptoterephthalate and 2 equiv of 3,6-dichlorotetrazine under very mild conditions. All corona[5]arenes adopted 1,2,4-alternate conformational structures in the crystalline state yielding similar nearly regular pentagonal cavities. Both the cavity size and the electronic property of the acquired macrocycles were fine-tuned by the nature of the bridging element X.
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