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A Dendrimer Chiroptical Switch Based on the Reversible Intramolecular Photoreaction of Anthracene and Benzene Rings |
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| Authors: | Wenjie Liu Dr Derong Cao Prof Dr Jinan Peng Hong Zhang Herbert Meier Prof Dr |
| Institution: | 1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86)?20‐871‐10245;2. School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528458 (China);3. Institute of Organic Chemistry, University of Mainz, Duesbergweg 10–14, 55099 Mainz (Germany) |
| Abstract: | 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. |
| Keywords: | dendrimers molecular switches cycloaddition chiroptics diastereomers |