Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes

A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylene bisimides are presumably contaminated with the respective 1,6 regioisomers. N,N‘-Dicyclohexyl-1,7-di...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-11, Vol.69 (23), p.7933-7939
Main Authors: Würthner, Frank, Stepanenko, Vladimir, Chen, Zhijian, Saha-Möller, Chantu R, Kocher, Nikolaus, Stalke, Dietmar
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Summary:A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylene bisimides are presumably contaminated with the respective 1,6 regioisomers. N,N‘-Dicyclohexyl-1,7-dibromoperylene bisimide 1,7-3 is obtained for the first time in isomerically pure form, and its structure is unequivocally confirmed by X-ray analysis. By using regioisomerically pure 1,7-dibromoperylene bisimide 1,7-3, 1,7-dipyrrolidinylperylene bisimides 4a−c and 1,7-dipyrrolidinylperylene bisanhydride 5 as well as the unsymmetrically difunctionalized 1-bromo-7-pyrrolidinyl- and 1-cyano-7-pyrrolidinylperylene bisimides 7 and 8 are synthesized in good yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048880d