Synthesis and stability of N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+): a [4]helicene with multiple redox states
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Synthesis and stability of N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+) : a [4]helicene with multiple redox states. / Sørensen, Thomas Just; Nielsen, Merete Folmer; Laursen, Bo Wegge.
In: ChemPlusChem, Vol. 79, No. 7, 2014, p. 1030-1035.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Synthesis and stability of N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+)
T2 - a [4]helicene with multiple redox states
AU - Sørensen, Thomas Just
AU - Nielsen, Merete Folmer
AU - Laursen, Bo Wegge
PY - 2014
Y1 - 2014
N2 - 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.
AB - 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.
KW - carbenium ions
KW - helicenes
KW - radicals
KW - redox chemistry
KW - synthetic methods
U2 - 10.1002/cplu.201402058
DO - 10.1002/cplu.201402058
M3 - Journal article
AN - SCOPUS:84904633476
VL - 79
SP - 1030
EP - 1035
JO - ChemPlusChem
JF - ChemPlusChem
SN - 2192-6506
IS - 7
ER -
ID: 131020541