Synthesis and stability of N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+): a [4]helicene with multiple redox states

Research output: Contribution to journalJournal articleResearchpeer-review

N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+) is a configurationally locked [4]helicene, a stable carbenium ion and a potent near-infrared emitter. The versatile synthesis and resolution into M and P enantiomers has made DMQA+ and its congener helicenium derivatives attractive chiral dyes and building blocks. In the present study, electrochemical and spectroscopic studies showed that several redox states of DMQA+ are accessible and stable. The cation stability towards nucleophiles is determined and it is shown that the addition of OH- proceeds with a surprisingly low rate of reaction. The synthetic methodologies leading to DMQA+ are described, and the chemistry occurring from the different redox states of DMQA is identified. This [4]helicene is shown to be a unique molecular framework that is stable as a neutral radical and very stable as a carbenium ion.

Original languageEnglish
JournalChemPlusChem
Volume79
Issue number7
Pages (from-to)1030-1035
Number of pages6
ISSN2192-6506
DOIs
Publication statusPublished - 2014

    Research areas

  • carbenium ions, helicenes, radicals, redox chemistry, synthetic methods

ID: 131020541