Azacalixquinarenes: From Canonical to (Poly-)Zwitterionic Macrocycles - Archive ouverte HAL
Journal Articles Journal of Organic Chemistry Year : 2019

Azacalixquinarenes: From Canonical to (Poly-)Zwitterionic Macrocycles

Abstract

Azacalixquinarenes, a new family of macrocycles constituted of diaminobenzoquinone diimine units linked by dinitrobenzene rings are synthesized by selected oxidation of the parent azacalixarenes. Crystallographic analyses of two compounds demonstrated the presence of (uncharged) canoni-cal and zwitterionic quinones within a single structure. The electron-withdrawing nature of the dinitrobenzene moieties can trigger the intramolecular H-transfer that generates zwitterionic-ground state quinones. The nature of the N-substituents and the polarity of the solvent have a crucial impact on the equilibrium between the canonical and zwitterionic forms that present distinct optical and electrochemical properties. Thus, within [4]-and [6]-membered macrocycles, poly-zwitterionic structures can be reached, as demonstrated experimentally and theoretically using first-principle approaches .
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Dates and versions

hal-02003222 , version 1 (31-01-2020)

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Simon Pascal, Lucien Lavaud, Cloé Azarias, Alexandre Varlot, Gabriel Canard, et al.. Azacalixquinarenes: From Canonical to (Poly-)Zwitterionic Macrocycles. Journal of Organic Chemistry, 2019, 84 (3), pp.1387-1397. ⟨10.1021/acs.joc.8b02847⟩. ⟨hal-02003222⟩
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