광감응형 아조벤젠기를 갖는 신규 플러렌 유도체의 합성과 물성분석

Synthesis and Characterization of Novel Fullerene(C60) Derivative with Photoresponsive Azobenzene Group

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, 13C-NMR, FAB-Mass or elemental analysis. Compound 1 exhibited the expected photoresponsive behavior. Chloroform solution(10-5M) 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.