Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
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Synthesis and Characterization of Novel Fullerene($C_{60}$) Derivative with Photoresponsive Azobenzene Group

광감응형 아조벤젠기를 갖는 신규 플러렌 유도체의 합성과 물성분석

  • 한기종 (풍림유화공업주식회사 연구소)
  • Received : 2014.02.07
  • Accepted : 2014.02.20
  • Published : 2014.03.30
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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.

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References

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