Diastereoselective formation of homochiral flexible perylene bisimide cyclophanes and their hybrids with fullerenes.

ABSTRACT: Cyclophanes of different ring sizes featuring perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) linked by flexible malonates were designed, synthesized, and investigated with respect to their structural, chemical and photo-physical properties. It is predominantly the number of PBIs and their geometric arrangement, which influence dramatically their properties. For example, two-PBI containing cyclophanes reveal physico-chemical characteristics that are governed by strong co-facial π-π interactions. This is in stark contrast to cyclophanes with either three or four PBIs. Key to co-facial π-π stackings are the flexible malonate linkers, which, in turn, set up the ways and means for diastereoselectivity of the homochiral PBIs at low temperatures, on one hand. In terms of selectivity, diast

SUBMITTER: Solymosi I 

PROVIDER: S-EPMC8653996 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature