Related Experiment Video
Updated: Apr 17, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
Synthesis and predetermined supramolecular chirality of carbohydrate-functionalized perylene bisimide derivatives
Ke-Rang Wang1, Dan Han, Guo-Jing Cao
1Key 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.
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.
More Related Videos
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Prochirality
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Chirality
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Molecules with Multiple Chiral Centers