Diarylethene계 광변색성 색소의 합성 및 그의 특성

The Synthesis of Diarylethene Photochromic Dyes and their Properties

  • 발행 : 1999.02.01

초록

In order to investigate the effect of connector structure of diarylethene derivatives on the maximum absorption band, thermal stability, and fatigue resistance to photoirradiation, the photochromic compounds, 1,2-dicyano-1,2-bis(2,3,5-trimethyl-4-thienyl) ethene(DYE I) and 2,3-bis(2,3,5-trimethyl-4-thienyl) maleic anhydride(DYE II) were synthesized. The DYE I has cyano groups and the DYE II has anhydride groups on the 1,2 carbon position as connector group, respectively. Identification of synthesized photochromic dyes were performed with $^1H-NMR$ and FT-IR spectrophotometers. The properties of photochromic compounds synthesized were examined in toluene solution and dispersed in polystyrene film. Upon the introduction of cyclic structure to the connector group, the maximum absorption band $({\lambda}_{max})$ shifted to longer wavelength, and the thermal stability and fatigue resistance increased. It is reasoned that the change of an electron-accepting ability at the 1,2 positions of aromatic rings or the variations of conjugation length affect the physical and chemical properties of the diarylethene derivatives. And the thermal stability and the fatigue resistance properties were rather enhanced dispersed in polymer film than in the solution state on account of less oxidation.

키워드

참고문헌

  1. Bull. Chem. Soc.Jpn. v.63 K. Uchida;Y. Nakayama;M. Irie
  2. J. Polym. Sci. v.6 H. Kamogawa;M. Kato;H. Sugiyama
  3. Functional Monomers and Polymers K. Takemoto;Y. Inaki
  4. Photophysical and Photochemical Properties of Aromatic Compounds J. Malkin
  5. Theses Collection of Chonnam University(Engineering) v.31 no.1 C. N. Choi
  6. 機能性色素の分子設計 時田澄男;松岡賢;古後義也;木原寬
  7. Processes in Photoreactive Polymers V. V. Kronggauz;A. D. Trifunac
  8. Proc. IEEE v.130 H. G. Heeler
  9. J. Org. Chem. v.53 M. Irie;M. Mohri
  10. Mol. Cryst. Liq. Cryst. v.227 M. Irie
  11. Bull. Chem. Soc. Jpn. v.64 Y. Nakayama;K. Hayashi;M. Irie
  12. Bull. Chem. Soc. Jpn. v.64 Y. Nakayama;K. Hayashi;M. Irie
  13. Photo-reactive Materials for Ultrahigh Density Optical Memory M. Irei
  14. J. Am. Chem. Soc., Macronolecules v.18 M. Irie;T. Iwayangi;Y. Taniguchi
  15. J. Polym. v.19 no.2 G. Kaempf
  16. 形狀記憶ボリマの開發と應用 入江政浩
  17. Makromol. Chem.; Rapid Commun v.10 S. Kohjiya
  18. 機能性高分子, 日本化學會編 新化學ライブラり- 緖方直哉
  19. 技術豫測 シリ-ズ;第2券 新素材編 壓川 博美
  20. J. Appl. Polym. Sci. v.28 K. Ishihara;M. Kim;I. Shinohara;T. Okano;K. Kataoka;Y. Sakurai
  21. 高分子 v.35 no.3 石原一彦
  22. J. Am. Chem. Soc. v.103 S. Shinkai;T. Nakaji;T. Okawa;K. Shigematsu;O. Manabe
  23. J. Appl. Phys. v.32 F. Tatezono;T. Harada;Y. Shimizu;M. Ohara;M. Irie
  24. J. Phys. Chem. Jpn. v.96 M. Irie;K. Sayo
  25. Structure Elucidation by NMR in Organic Chemistry E. Breimaier
  26. a Guide to the Complete Interpretation of Infrared Spectra of Organic Structures N. P. G. Roeges
  27. Introduction to Organic Spectroscopy J. B. Lambert;H. F. Shurvell;D. A. Lightner;R. G. Cooks
  28. Infrared Characteristic Group Frequencies G. Socrates
  29. J. Am. Chem. v.114 M. Irie;O. Miyatake;K. Uchida
  30. J. Am. Chem. Soc. v.116 M. Irie;O. Miyatake;T. Eriguchi
  31. 基礎有機化學(第2版) 向山光昭
  32. Principles of Photochemistry J. A. Barltrop;J. D. Coyle
  33. Color Chemistry, 2th H. Zollinger
  34. 新化學ライプラリ 光化學の世界 德丸克巳;日本化學會編
  35. Special Polymers for Electronics & Optoelectronics J. A. Chilton;M. T. Goosey
  36. 機能性色素 大河原 信;松岡 賢;平島恒豪;北尾悌次郞
  37. 增感劑 德丸克己;大河原 信
  38. Chemical Physics of Polymer Degradation and Stabilization N. M. Ernanuel;A. L. Buchachenko
  39. Fundamentals of Polymer Degradation and Stabiliza- tion N. S. Allen;M. Edge
  40. 情報システムと機能材料 小門 宏;高田久夫