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 af dette arbejde

Kemisk Institut

18 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	ChemPlusChem
Vol/bind	79
Udgave nummer	7
Sider (fra-til)	1030-1035
Antal sider	6
ISSN	2192-6506
DOI	https://doi.org/10.1002/cplu.201402058
Status	Udgivet - 2014

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10.1002/cplu.201402058

Citationsformater

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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.",

keywords = "carbenium ions, helicenes, radicals, redox chemistry, synthetic methods",

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

year = "2014",

doi = "10.1002/cplu.201402058",

language = "English",

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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

M3 - Journal article

AN - SCOPUS:84904633476

SN - 2192-6506

VL - 79

SP - 1030

EP - 1035

JO - ChemPlusChem

JF - ChemPlusChem

IS - 7

ER -

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

Abstract

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Citationsformater

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