Synthesis, Photochromism and Optical Storage of a Novel Unsymmetrical Diarylethene Compound

Abstract:

A new unsymmetrical photochromic diarylethene 1-[2,5-dimethyl-3-thienyl]-2-[3,5-difluorophenyl]perfluoroyclopentene (1a) was synthesized, its photochromic, fluorescent and optical strorage properties were examined, the result indicated that the diarylethene 1a changed the color from colorless to purple upon irradiation with 313 nm UV light, in which absorption maxima were observed at 542nm and 556nm in hexane and PMMA film, respectively. This new photochromic system exhibited remarkable fluorescence intensity and clear fluorescent switches by photoirradiation in PMMA film. The results showed that the cyclization/cycloreversion process of the compound was determined to be the zeroth/first order reaction. This new photochromic system also exhibited remarkable optical storage character.

• Periodical: Advanced Materials Research (Volumes 156-157)
• Pages: 665-669
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.156-157.665
• Online since: October 2010
• Authors: Tao Feng Wang, Zhi Gang Liu, Shou Zhi Pu, Gang Liu
• Keywords: Diarylethene, Fluorescence Switch, Optical Recording Medium

References

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

[2] S. Z. Pu, L. S. Yan, Z. D. Wen, G. Liu and L. Shen: J. Photochem. Photobiol. A: Chem. Vol. 196 (2008), p.84.

[3] Y. Chen, D. X. Zeng, N. Xie, Y. Z. Dang: Org. Chem. ACS publication, vol. 70(2005), p.5001.

[4] D. Dulic, T. Kudernac, A. Puzys, B. L. Feringa and B. J. Wees: Adv. Mater. Vol. 196 (2007), p.2898.

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

[6] M. Morimoto, M. Irie: Chem. Com, Vol. 12(2005). p.3895.

[7] M. Irie: Chem. Rev. American Chemical Society, vol. 100(2000), p.1685.

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

[9] M. Irie, K. Uchida: Bull. Chem. Soc. Vol. 71(1998), p.985.

[10] S. Z. Pu, T. S. Yang and G. Z. Li: Tetrahedron Lett. Vol. 47 (2006), p.3167.

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

[12] S. Z. Pu, T. S. Yang, J. K. Xu and B. Chen: Tetrahedron Lett., vol. 47(2006), p.6473.

[13] C. B. Fan, S. Z. Pu, G. Liu, J. K. Xu and C. H. Zheng: Journal of Materials Science＆ Engineering, vol. 25(2007), p.943.

[14] M. Irie, T. Lifka, S. Kobatake, N. Kato: J. Am. Chem. Soc, vol. 122(2000), p.4871.

[15] S. Z. Pu, F. S. Zhang, J. K. Xu, L. Shen, Q. Xiao, B. Chen: Mater. Lett. Vol. 60 (2006), p.485.

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

[17] T. B. Norsten, N. R. Branda: J. Am. Chem. Soc, vol. 128(2001), p.178.