Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Synthesis of Bis(dithiobenzil) Metal Complex and Its Photostability

Bis(dithiobenzil) 금속 화합물의 합성 및 광안정성

  • Lee, Gun-Dae (Division of Applied Chemical Engineering, Pukyong National University) ;
  • Park, Na Yi (Division of Applied Chemical Engineering, Pukyong National University) ;
  • Jeon, Seung Yup (Division of Applied Chemical Engineering, Pukyong National University) ;
  • Heo, Jin (Division of Applied Chemical Engineering, Pukyong National University) ;
  • Son, Dae Hee (Research & Development Team, CFC) ;
  • Hwang, Tae Kyung (Research & Development Team, Mapro Co. Ltd.) ;
  • Park, Seong Soo (Division of Applied Chemical Engineering, Pukyong National University)
  • 이근대 (부경대학교 응용화학공학부) ;
  • 박나이 (부경대학교 응용화학공학부) ;
  • 전승엽 (부경대학교 응용화학공학부) ;
  • 허진 (부경대학교 응용화학공학부) ;
  • 손대희 (CFC 연구개발팀) ;
  • 황태경 ((주)마프로 연구개발팀) ;
  • 박성수 (부경대학교 응용화학공학부)
  • Received : 2007.03.30
  • Accepted : 2007.08.27
  • Published : 2007.10.10
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Abstract

Bis(dithiobenzil) metal complex, used as functional NIR absorbing dye and photostabilizer, was synthesized using bezoin and anisoin as intermediate compounds. And squarylium, a charge generation material, was synthesized to find its photostability effect. The structure of the product was determined by $^1H-NMR$ and FT-IR and the thermal property was analyzed by DSC and TGA. Optical property and photostability were determined by UV-Vis-NIR spectroscopy. High absorbance was obtained in the NIR range and maximum absorbing wavelength was shifted depending on the nature and position of substituent in the bis(dithiobenzil) metal complex. The photofading effect of squarylium decreased by the addition of bis(dithiobenzil) metal complex.

본 연구에서는 기능성 근적외선 흡수색소 및 광안정제로 사용되는 bis(dithiobenzil) 금속 화합물은 중간체인 benzoin 및 anisoin을 먼저 합성하고 이들을 전구체로 사용하여 합성하였다. 또한, bis(dithiobenzil) 금속 화합물의 광안정성 효과를 확인하기 위하여 전하발생재료인 squarylium을 합성하였다. 중간체 및 최종 생성물의 구조는 핵자기 공명 분석기와 적외선 분광기를 이용하여 확인하였고, 열적 특성은 시차열분석기 및 열중량분석기를 이용하여 분석하였다. 광학 특성과 광안정성 효과는 UV-Vis-NIR 분광기를 이용하여 측정 분석하였다. 합성한 bis(dithiobenzil) 금속 화합물은 근적외선 영역에서 우수한 흡광특성을 나타내었고, 치환기의 종류 및 위치에 따라 최대흡수파장이 이동하였다. 또한, squarylium에 bis(dithiobenzil) 금속 화합물을 첨가하면 squarylium의 광퇴색현상을 감소시켰다.

Keywords

Acknowledgement

Supported by : 에너지관리공단

References

  1. M. Matsuoka, Infrared Absorbing Dyes, Plenum Press, New York (1990)
  2. K. A. Bello and J. O. Ajayi, Dyes and Pigments, 31, 79 (1996)
  3. E. I. Stiefel, Progress in Inorganic Chemistry: Dithiolene Chemistry, John Wiley & Sons, New York (2004)
  4. R. Kato, Chem. Rev., 104, 5319 (2004) https://doi.org/10.1021/cr030655t
  5. Z. Dai, L. Qun, and B. Peng, Dyes and Pigment, 35, 23 (1997)
  6. M. O. Liu, C. H. Tai, W. Y. Wang, J. R. Chen, A. T. Hu, and T. H. Wei, J. Organomet. Chem., 689, 1078 (2004) https://doi.org/10.1016/j.jorganchem.2004.01.017
  7. D. Qing, C. X. Feng, C. Hong, G. Xing, Z. X. Ping, and C. Zhusheng, Supramolecular Science, 5, 531 (1998)
  8. J. S. Buck and W. S. Ide, Mixed benzoins I, J. Am. Chem. Soc., 52, 220 (1930) https://doi.org/10.1021/ja01364a032
  9. G. Sumrell, J. I. Stevens, and G. E. Goheen, J. Org. Chem., 22, 39 (1957) https://doi.org/10.1021/jo01352a009
  10. G. N. Schrauzer and V. P. Mayweg, J. Am. Chem. Soc., 87, 1484 (1965)
  11. N. Kuramoto, K. Natsukawa, and K. Asao, Dyes and Pigments, 11, 21 (1989) https://doi.org/10.1016/0143-7208(89)85023-5
  12. S. H. Kim, S. H. Hwang, J. J. Kim, C. M. Yoon, and S. R. Keum, Dyes and Pigments, 37, 145 (1998)