Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 3, Pages 1387-1397Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02847
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- ANR
- French National Agency for Research [ANR-11-EQPX-0004]
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Azacalixquinarenes, a new family of macrocycles composed of diaminobenzoquinone diimine units linked by dinitrobenzene rings, are synthesized by selective oxidation of the parent azacalixarenes. Crystallographic analyses of two compounds demonstrated the presence of canonical (uncharged) 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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