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http://dx.doi.org/10.12925/jkocs.2014.31.1.50

Synthesis and Characterization of Novel Fullerene($C_{60}$) Derivative with Photoresponsive Azobenzene Group  

Han, Ki-Jong (R&D Center, Poong Lim Oil Chemical)
Publication Information
Journal of the Korean Applied Science and Technology / v.31, no.1, 2014 , pp. 50-58 More about this Journal
Abstract
A novel fullerene derivative with photoresponsive azobenzene group was designed and synthesized, and its photoresponsive properties were reported. Starting from 4-nitrophenol, compound 1, which is containing fullerene moiety connected to azobenzene group through covalent linkage was synthesized by 5 steps. All the intermediates and the final compound were characterized by $^1H$, $^{13}C$-NMR, FAB-Mass or elemental analysis. Compound 1 exhibited the expected photoresponsive behavior. Chloroform solution($10^{-5}M$) of it served to maximize the absorption at 351 nm corresponding to the trans-azobenzene chromophore. Irradiation of this solution with 365 nm light resulted in photoisomerization to cis-azobenzene, as evidenced by decrease in the absorbance at 351 nm and an increase in absorbance at 450nm. A photostationary state was reached within about 150 s. Thermal reversion to the original spectrum was observed over the course of about 6 h at room temperature in the dark. However, exposure to bright sun light for about 5 s also effect almost complete reversion to the trans-isomer. This indicates that there is no strong steric influence on the trans-cis reversible isomerization of compound 1.
Keywords
photoresponsive; azobenzene; fullerene; photoisomerization;
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