Ambient Stable Zwitterionic Perylene Bisimide-Centered Radical

David Schmidt; David Bialas; Frank Würthner

doi:10.1002/ANIE.201408067

Ambient Stable Zwitterionic Perylene Bisimide-Centered Radical

David Schmidt
, David Bialas
, Frank Würthner

School of Science (Behrend)

Research output: Contribution to journal › Article › peer-review

103 Scopus citations

Abstract

The unexpected introduction of a cationic imidazolium substituent in the 2-position of a tetrachloro-substituted perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) by the reaction of PBI-Cl₄ 1 with the N-heterocyclic carbene 1,3-diiso-propyl-imidazolin-2-ylidene (ⁱPr₂Im 2) enables the isolation of an ambient stable zwitterionic radical. The remarkable stability of this unprecedented PBI-centered radical facilitates the complete characterization by several spectroscopic methods as well as single crystal structure analysis. Redox studies revealed thatⁱPr₂Im-PBI-Cl₄ 4 can be transferred reversibly to the corresponding anion and cation, respectively, even on a preparative scale.

Original language	English (US)
Pages (from-to)	3611-3614
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	12
DOIs	https://doi.org/10.1002/ANIE.201408067
State	Published - Mar 16 2015

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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title = "Ambient Stable Zwitterionic Perylene Bisimide-Centered Radical",

abstract = "The unexpected introduction of a cationic imidazolium substituent in the 2-position of a tetrachloro-substituted perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) by the reaction of PBI-Cl4 1 with the N-heterocyclic carbene 1,3-diiso-propyl-imidazolin-2-ylidene (iPr2Im 2) enables the isolation of an ambient stable zwitterionic radical. The remarkable stability of this unprecedented PBI-centered radical facilitates the complete characterization by several spectroscopic methods as well as single crystal structure analysis. Redox studies revealed thatiPr2Im-PBI-Cl4 4 can be transferred reversibly to the corresponding anion and cation, respectively, even on a preparative scale.",

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T1 - Ambient Stable Zwitterionic Perylene Bisimide-Centered Radical

AU - Schmidt, David

AU - Bialas, David

AU - Würthner, Frank

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Y1 - 2015/3/16

N2 - The unexpected introduction of a cationic imidazolium substituent in the 2-position of a tetrachloro-substituted perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) by the reaction of PBI-Cl4 1 with the N-heterocyclic carbene 1,3-diiso-propyl-imidazolin-2-ylidene (iPr2Im 2) enables the isolation of an ambient stable zwitterionic radical. The remarkable stability of this unprecedented PBI-centered radical facilitates the complete characterization by several spectroscopic methods as well as single crystal structure analysis. Redox studies revealed thatiPr2Im-PBI-Cl4 4 can be transferred reversibly to the corresponding anion and cation, respectively, even on a preparative scale.

AB - The unexpected introduction of a cationic imidazolium substituent in the 2-position of a tetrachloro-substituted perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) by the reaction of PBI-Cl4 1 with the N-heterocyclic carbene 1,3-diiso-propyl-imidazolin-2-ylidene (iPr2Im 2) enables the isolation of an ambient stable zwitterionic radical. The remarkable stability of this unprecedented PBI-centered radical facilitates the complete characterization by several spectroscopic methods as well as single crystal structure analysis. Redox studies revealed thatiPr2Im-PBI-Cl4 4 can be transferred reversibly to the corresponding anion and cation, respectively, even on a preparative scale.

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AN - SCOPUS:84929579292

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 12

ER -

Ambient Stable Zwitterionic Perylene Bisimide-Centered Radical

Abstract

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