Abstract
Photoswitchable glycomacrocycles are of great interest because of their intrinsic
chirality, their variable ring sizes, molecular shapes, and their potential applications
in chemistry, materials science, biology, and drug discovery. Through a one-pot double
click reaction, we have successfully synthesized a new 20-membered azobenzene-based
glycomacrocycle bearing two triazole rings. The macrocyclization conditions have been
optimized to achieve a yield of up to 55% for the synthesis of hundreds of milligrams
of the compound E-1. The macrocyclic glycoazobenzene E-1 can be reversibly photoisomerized between E and Z isomers, with good photoconversion yields, high fatigue resistance, and bistability
of both E and Z isomers. The X-ray structures have been obtained for both E- and Z-isomers of 1. The chiroptical activity has also been observed with the E-1.
Keywords
Azobenzene (AB), Chiroptical property - Click reaction - Glycomacrocycle - Photoswitching
