Synthesis, Photochromism and Optical Recording Properties of a Diarylethene Materials Bearing an Isoxazole Unit

Abstract:

A new unsymmetrical photochromic diarylethene, 1-(3,5-dimethyl-4-isoxazolyl)-2-[2-methyl-5-(4-formylphenyl)-3- thienyl]perfluorocyclopentene(1a) were synthesized, and its properties, such as photochromism and fluorescence properties, were investigated in detail. The results showed that this compound had good thermal stability and exhibited reversible photochromism, changing from colorless to darkred after irradiation with UV light both in solution and in PMMA amorphous film, the maxima absorption of its closed-ring isomer 1b are 529 nm and 541 nm respectively. The open-ring isomer of the diarylethene 1a exhibited relatively strong fluorescence at 492 nm in hexane solution (2 × 10^-5 mol/L) when excited at 418 nm. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light. This new photochromic system also exhibited remarkable optical storage character.

• Periodical: Advanced Materials Research (Volume 583)
• Pages: 125-129
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.583.125
• Online since: October 2012
• Authors: Xiao Ting Li, Hui Li, Gang Liu
• Keywords: Diarylethene Materials, Fluorescence, Optical Storage, Photochromism

References

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

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

[3] K. Matsuda and M. Irie: J. Photochem. Photobiol. C: Photoch. Rev. Vol. 5 (2004), p.169.

[4] M. Morimoto and M. Irie: Chem. Commun. 2005, p.3895.

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

[6] J.K. W. Lee, C.C. Ko, K.M.C. Wong, N.Y. Zhu and V.W.W. Yam: Organometall. Vol. 26 (2007), p.12.

[7] Y.L. Feng, Y.L. Yan, S. Wang, W.H. Zhu, S.X. Qian and H. Tian: J. Mathematical Chem. Vol. 16 (2006), p.3685.

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

[9] S.Z. Pu, T.S. Yang, J.K. Xu, L. Shen and G. Liu: Tetrahedron Vol. 61 (2005), p.6623.

[10] S. Yamamoto, K. Matsuda and M. Irie: Chem. Eur. J. Vol. 9 (2005), p.4878.

[11] C.B. Fan, S.Z. Pu, G. Liu and T.S. Yang: J. Photochem. Photobiol. A: Chem. Vol. 194 (2008), p.333.

[12] K. Morimitsu, K. Shibata, S. Kobatake and M. Irie: J. Org. Chem. Vol. 67 (2002), p.4574.

[13] T. Fukaminato, T. Sasaki, T. Kawai, N. Tamai and M. Irie: J. Am. Chem. Soc. Vol. 126 (2004), p.14843.

[14] B.Z. Chen, M.Z. Wang and H. Tian: Chem. Commun. 2002, p.1060.

[15] B.L. Yao, Y.L. Wang and M. Lei: Opt. Exp. Vol. 13 (2005), p.20.