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Synthesis and anion binding properties of phthalimide-containing corona[6]arenes.

ABSTRACT: Functionalized O₆-corona[3]arene[3]tetrazines were synthesized efficiently and conveniently by means of a macrocyclic condensation reaction between N-functionalized 3,6-dihydroxyphthalimides and 3,6-dichlorotetrazine under mild conditions in a one-pot reaction manner. The novel macrocycles exist as a mixture of rapidly interconvertible conformers in solution while in the solid state they adopt the conformation in which three phthalimide units are cis,trans-orientated. Acting as electron-deficient macrocyclic hosts, the synthesized O₆-corona[3]arene[3]tetrazines self-regulated conformational structures to complex anions in the gas phase and in the solid state owing to the anion-? noncovalent interactions between anions and the tetrazine rings.

SUBMITTER: Gu MD

PROVIDER: S-EPMC6720058 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Synthesis and anion binding properties of phthalimide-containing corona[6]arenes.

Gu Meng-Di MD Lu Yao Y Wang Mei-Xiang MX

Beilstein journal of organic chemistry 20190821

Functionalized O6-corona[3]arene[3]tetrazines were synthesized efficiently and conveniently by means of a macrocyclic condensation reaction between N-functionalized 3,6-dihydroxyphthalimides and 3,6-dichlorotetrazine under mild conditions in a one-pot reaction manner. The novel macrocycles exist as a mixture of rapidly interconvertible conformers in solution while in the solid state they adopt the conformation in which three phthalimide units are cis,trans-orientated. Ac ...[more]

PMID: 31501664

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