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A Dendrimer Chiroptical Switch Based on the Reversible Intramolecular Photoreaction of Anthracene and Benzene Rings
Author(s) -
Liu Wenjie,
Cao Derong,
Peng Jinan,
Zhang Hong,
Meier Herbert
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000159
Subject(s) - anthracene , dendrimer , intramolecular force , benzene , ring (chemistry) , photochemistry , diastereomer , cycloaddition , chemistry , irradiation , materials science , stereochemistry , polymer chemistry , organic chemistry , catalysis , physics , nuclear physics
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 [4π+4π] 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 of chiroptical switch has been created that has optical rotation values as output signals.