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

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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.

OriginalsprogEngelsk
TidsskriftChemPlusChem
Vol/bind79
Udgave nummer7
Sider (fra-til)1030-1035
Antal sider6
ISSN2192-6506
DOI
StatusUdgivet - 2014

ID: 131020541