Würthner Frank, Stepanenko Vladimir, Chen Zhijian, Saha-Möller Chantu R, Kocher Nikolaus, Stalke Dietmar
Institutes of Organic Chemistry and Inorganic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
J Org Chem. 2004 Nov 12;69(23):7933-9. doi: 10.1021/jo048880d.
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.
报道了一项关于苝二酐与环己胺溴化及随后亚胺化的详细研究。目前的结果表明，先前报道的1,7 - 二官能化苝双酰亚胺可能被各自的1,6区域异构体污染。首次以异构体纯的形式获得了N,N'-二环己基-1,7 - 二溴苝双酰亚胺1,7 - 3，其结构通过X射线分析得到明确证实。通过使用区域异构体纯的1,7 - 二溴苝双酰亚胺1,7 - 3，以良好的产率合成了1,7 - 二吡咯烷基苝双酰亚胺4a - c和1,7 - 二吡咯烷基苝二酐5以及不对称双官能化的1 - 溴 - 7 - 吡咯烷基 - 和1 - 氰基 - 7 - 吡咯烷基苝双酰亚胺7和8。
