Ambient Stable Zwitterionic Perylene Bisimide‐Centered Radical. Issue 12 (12th November 2014)

• Record Type: Journal Article
• Authors: Schmidt, David; Bialas, David; Würthner, Frank
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 12(2015)
• Page Start: 3611
• Page End: 3614
• Publication Date: 2014-11-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201408067
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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<bold>1</bold> with the N‐heterocyclic carbene 1, 3‐di‐iso‐propyl‐imidazolin‐2‐ylidene (ⁱPr₂Im <bold>2</bold>) 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 that ⁱPr₂Im‐PBI‐Cl₄<bold>4</bold> can be transferred reversibly to the corresponding anion and cation, respectively, even on a preparative scale.</p> </abstract>