A Dendrimer Chiroptical Switch Based on the Reversible Intramolecular Photoreaction of Anthracene and Benzene Rings

2010

A series of Fréchet-type dendrimers with 9-benzyloxymethylanthracene cores were synthesized and characterized. The chiral source for the dendrimers was an (S)-2-methyl-1-butoxy group in the 3-position of the benzene ring. Irradiation at 366 nm of a dilute benzene solution led to the formation of two diastereomers (1:1) through a quantitative intramolecular [4pi+4pi] cycloaddition between the central anthracene ring and the neighboring benzene ring. The process can be reversed with 254 nm UV light or heat. The benzene rings in the dendrons work as a light-harvesting system. The optical rotation values measured for the reversible process showed fatigue resistance. Thus, a promising new type o…