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Ambient Stable Zwitterionic Perylene Bisimide‐Centered Radical
Author(s) -
Schmidt David,
Bialas David,
Würthner Frank
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201408067
Subject(s) - perylene , chemistry , substituent , carbene , cationic polymerization , radical ion , photochemistry , redox , ion , medicinal chemistry , polymer chemistry , organic chemistry , catalysis , molecule
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‐Cl 4 1 with the N‐heterocyclic carbene 1,3‐di‐iso‐propyl‐imidazolin‐2‐ylidene ( i Pr 2 Im 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 that i Pr 2 Im‐PBI‐Cl 4 4 can be transferred reversibly to the corresponding anion and cation, respectively, even on a preparative scale.