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

Thomas Just Sørensen; Merete Folmer Nielsen; Bo Wegge Laursen

doi:10.1002/cplu.201402058

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

Thomas Just Sørensen, Merete Folmer Nielsen, Bo Wegge Laursen^*

^*Corresponding author for this work

Department of Chemistry

18 Citations (Scopus)

Abstract

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 language	English
Journal	ChemPlusChem
Volume	79
Issue number	7
Pages (from-to)	1030-1035
Number of pages	6
ISSN	2192-6506
DOIs	https://doi.org/10.1002/cplu.201402058
Publication status	Published - 2014

Keywords

carbenium ions
helicenes
radicals
redox chemistry
synthetic methods

Access to Document

10.1002/cplu.201402058

Cite this

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

abstract = "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.",

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author = "S{\o}rensen, {Thomas Just} and Nielsen, {Merete Folmer} and Laursen, {Bo Wegge}",

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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

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