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

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Standard

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.

I: ChemPlusChem, Bind 79, Nr. 7, 2014, s. 1030-1035.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Sørensen, TJ, Nielsen, MF & Laursen, BW 2014, 'Synthesis and stability of N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+): a [4]helicene with multiple redox states', ChemPlusChem, bind 79, nr. 7, s. 1030-1035. https://doi.org/10.1002/cplu.201402058

APA

Sørensen, T. J., Nielsen, M. F., & Laursen, B. W. (2014). Synthesis and stability of N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+): a [4]helicene with multiple redox states. ChemPlusChem, 79(7), 1030-1035. https://doi.org/10.1002/cplu.201402058

Vancouver

Sørensen TJ, Nielsen MF, Laursen BW. Synthesis and stability of N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+): a [4]helicene with multiple redox states. ChemPlusChem. 2014;79(7):1030-1035. https://doi.org/10.1002/cplu.201402058

Author

Sørensen, Thomas Just ; Nielsen, Merete Folmer ; Laursen, Bo Wegge. / Synthesis and stability of N,N′-Dialkyl-1,13-dimethoxyquinacridinium (DMQA+) : a [4]helicene with multiple redox states. I: ChemPlusChem. 2014 ; Bind 79, Nr. 7. s. 1030-1035.

Bibtex

@article{51bf8fa6039140068920211020990dee,
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",
volume = "79",
pages = "1030--1035",
journal = "ChemPlusChem",
issn = "2192-6506",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "7",

}

RIS

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