Synthesis, Photochromism and Application of a Novel Diarylethene Bearing a Thiazole Unit

Abstract:

A new photochromic diarylethene compound 1-(2, 4-dimethyl-thiazole-3-yl)-2- [2-methyl -5-(3-cyanophenyl)-3-thienyl]perfluorocyclopentene 1a was synthesized and its photochromic properties, such as phoochromism, fluorescence switch and optical recording were investigated detail. The result showed that this diarylethene compound showed good reversible photochromism. Upon irradiated UV light it changes from colorless to orange both in solution and in PMMA amorphous film. In addition, the fluorescence spectra of diarylethene 1a were nearly quenched with the concentration increased. Finally, using diarylethene 1c as recording medium, polarization optical recording was carried out successfully.

• Periodical: Advanced Materials Research (Volumes 197-198)
• Pages: 452-455
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.197-198.452
• Online since: February 2011
• Authors: Ren Jie Wang, Hong Ying Xia, Shou Zhi Pu
• Keywords: Diarylethene, Fluorescence Switch, Optical Recording, Photochromism

References

[1] A. Bianco, C. Bertarelli, M. C. Gallazzi, G. Zerbi, E. Giro: Molinari, E. Astron. Nachr. 326 (2005), p.370.

DOI: 10.1002/asna.200410355

[2] T. Tsujioka, M. Shimizu and E. Ishihara: Appl. Phys. Lett. 87 (2005), p.213506.

[3] T. Tsujiokka, N. Iefuji, A. Jiapaer, M. Irie, S. Nakamura: Appl. Phys. Lett. 89 (2006), p.222102.

DOI: 10.1063/1.2387898

[4] M. Irie: Chem. Rev. 100 (2000), p.1685.

[5] H. Tian, S. J. Yang: Chem. Soc. Rev. 33 (2004), p.85.

[6] M. Frigoli, C. Welch, G. H. Mehl: J. Am. Chem. Soc. 126 (2004), p.15382.

[7] K. Higashiguchi, K. Matsuda, N. Tanifuji and M. Irie: J. Am. Chem. Soc. 127 (2005), p.8922.

[8] E. Kim, M. Kim, K. Kim: Tetrahedron. 62 (2006), p.6814.

[9] T. Yamaguchi, M. Irie: J. Org. Chem. 70 (2005), p.10323.

[10] X. D. Deng, L. S. Liebeskind: J. Am. Chem. Soc. 123 (2001), p.7703.

[11] K. Uchida, T. Matsuoka, K. Sayo, M. Iwamoto, S. Hayashi, M. Irie: Chem. Lett. (1999), p.835.

[12] S. Z. Pu, G. Liu, L. Shen, J. K. Xu: Org. Lett. 9 (2007), p.2139.

[13] G. Favaro, U. Mazzucato, F. Ortica, P. Smimmo: Inorg. Chim. Acta. 360 (2007), p.995.

DOI: 10.1016/j.ica.2006.07.007

[14] T. Yamaguchi. M. Irie: Tetrahedron Lett. 47 (2006), p.1267.

[15] K. Uchida, T. Ishikawa, M. Takeshita, M. Irie: Tetrahedron. 54(24) (1998), p.6627.

[16] S. Takami, M. Irie: Tetrahedron. Elsevier B. V. Netherlands. 60(29) (2004), p.6155.

[17] K. Yagi, M. Irie: Bull. Chem. Soc. Jpn. 76(8) (2003), p.1625.

[18] T. Yamaguchi and M. Irie: Tetrahedron Lett. Vol. 47 (2006), p.1267.

[19] G. Liu, T. Zheng, S. Z. Pu, and J. K. Xu: Acta Cryst. Vol. 62 (2006), p. o2877.

[20] K. Kasatani, S. Kambe, M. Irie : J. Photochem. Photobiol. A. 122 (1999), p.11.

[21] S. Z. Pu, J. K. Xu, L. Shen, Q. Xiao, T. S. Yang, and G. Liu: Tetrahedron Lett. Vol. 46 (2005), p.871.

[22] C. B. Fan, S. Z. Pu, G. Liu and T. S. Yang: J. Photochem. Photobiol. Vol. 197 (2008), p.415.

[23] T. Fukaminato, T. Kawai, S. Kobatake, and M. Irie: J. Phys. Chem. Vol. 107 (2003), p.8372.

[24] S. Z. Pu, T. S. Yang, B. L. Yao, Y. Wang, M. Lei, and J. K. Xu: Mater. Lett. Vol. 61 (2007), p.855.