Synthesis and Photochromism Studies of 1-(2,5-Dimethyl-3-Thienyl)-2-[2-Methyl-5-Naphthyl-3-Thienyl] Perfluorocyclopentene

Abstract:

A novel photochromic diarylethene 1a has been synthesized. Its photochemical properties, including photochromic behavior and kinetics, have been investigated in detail. The result indicated that the Diarylethene 1a changed the color from colorless to pink irradiation with 297 nm UV light, in which absorption maxima were observed at 548 nm in hexane. The photochromic reaction kinetics indicated that the cyclization processes of 1a belong to the zeroth order reaction and the cycloreversion process belong to the first order reaction. The back irradiation by appropriate wavelength visible light regenerated its open-ring isomers and recovered the original emission intensity.

• Periodical: Advanced Materials Research (Volume 952)
• Pages: 109-112
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.952.109
• Online since: May 2014
• Authors: Xiao Rong Dong, Hong Yan Xu, Shou Zhi Pu*
• Keywords: Diarylethene, Fluorescence Switch, Kinetic, Photochromism

References

[1] T. Tsujioka and M. Irie: J. Photochem. Photobiol. C. Vol. 11 (2010), p.1.

[2] H.L. Liu, S.Z. Pu, G. Liu and B. Chen: Tetrahedron Lett Vol. 54 (2013), p.646.

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

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

[5] D. Dulic, T. Kudernac, A. Puzys, B.L. Feringa and B.J. Wees: Adv. Mater Vol 19 (2007), p.2898.

[6] S.J. Luo, K.X. Chen, L.C. Cao, G.D. Liu, Q.S. He and Y. Chen: Opt. Express. Vol 13 (2005), p.3123.

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

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

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

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

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

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

[13] S. Yamamoto, K. Matsuda and M. Irie: Chem. Eur. J. Vol. 9 (2003), p.4878.

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

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

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

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

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