title: Synthesis and predetermined supramolecular chirality of carbohydrate-functionalized perylene bisimide derivatives.
abstract: Eight carbohydrate-modified perylene bisimides (PBI-4 lac-2 lac, PBI-4 lac-2 Man, PBI-4 lac-2 Gal, PBI-4 lac-2 Mal, PBI-4 Man-2 Man, PBI-4 Man-2 lac, PBI-4 Man-2 Gal and PBI-4 Man-2 Mal) were synthesized, and the following predetermined supramolecular chirality rule was found: perylene bisimides modified with disaccharides (D-lactose and D-maltose) at the imide position generated right-handed chirality, and those modified with monosaccharides (D-mannose and D-galactose) generated left-handed chirality, when D-lactose or D-mannose was substituted in the bay positions of perylene bisimides with amide bonds as the linking spacers. These results may be because of the difference in the stacking angle of the perylene bisimide backbones induced by the steric effect and the additional hydrogen bonds between the disaccharide residues. This study provides an important design rule for predetermined chiral self-assembly of perylene bisimides.
authors: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, NO. 180, Wusi East Road, Baoding, 071002 (P.R. China); Key Laboratory of Medicinal Chemistry and Molecular Diagnosis, Hebei University, NO.180, Wusi East Road, Baoding, 071002 (P.R. China). kerangwang@hbu.edu.cn.
authors: Ke-Rang
authors: KR
authors: Wang
authors: Dan
authors: D
authors: Han
authors: Guo-Jing
authors: GJ
authors: Cao
authors: Xiao-Liu
authors: XL
authors: Li
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D002241:Carbohydrates; D007094:Imides; C510697:perylene bisimide; D010569:Perylene
keywords: carbohydrates; circular dichroism; perylene bisimide; self-assembly; supramolecular chirality