Synthesis and Properties of a Novel Unsymmetrical Diarylethene with a Benzothiophene and a Thiazole Group

Abstract:

A new unsymmetrical photochromic diarylethene 1o, which is named 1-(2-methyl-benzothiophene)-2-(2,4-dimethyl-5-thiazoly) perfluorocyclopentene, was synthesized. In the meantime, its photochromic, kinetics and fluorescence properties were investigated in detail. The result indicated that this diarylethene had good thermal stability and exhibited reversible photochromism, changing the color from colorless to orange in hexane solution upon appropriate irradiation with 297 nm UV light, respectively. What is more, the kinetic experiments illustrated that the cyclization/cycloreversion process of this compound was determined to be the zeroth/first reaction. The fluorescence intensity of diarylethene decreased dramatically along with the photochromism from open-ring isomer to closed-ring isomer upon irradiation with UV light in hexane solution. In addition, the results demonstrated that the unsymmetrical diarylethene compound 1o, which we have synthesized, had attractive properties for potential application in optical storage.

• Periodical: Advanced Materials Research (Volume 788)
• Pages: 190-193
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.788.190
• Online since: September 2013
• Authors: Hong Jing Jia, Shou Zhi Pu, Cong Bin Fan
• Keywords: Fluorescence, Kinetic, Photochromic, Unsymmetrical Diarylethene

References

[1] Y. Chen, C.M. Wang, M.G. Fan, B.L. Yao and N. Menke: Opt. Mater. Vol. 26 (2004), p.75.

[2] F.M. Raymo and M. Tomasulo: Chem. Soc. Rev. Vol. 34 (2005), p.327.

[3] K. Matsuda and M. Irie: Chem. Lett. Vol. 35 (2006), p.1204.

[4] W. Feng, K. Huang and M.X. Wang: Chin. Phys. Vol. 14 (2005), p.306.

[5] G. Berkovic, V. Krongauz and V. Weiss: Chem. Rev. Vol. 100 (2000), p.1741.

[6] Y.C. Liang, A.S. Dvornikov and P.M. Rentzepis: Macromolecules Vol. 35 (2002), p.9377.

[7] J. Yin, X. Cao, F. Yu, G.A. and S.H. Liu: Tetrahedron Lett. Vol. 49 (2008), p.1582.

[8] G. M. Tsivgoulis and J.M. Lehn: Angew. Chem. Int. Ed. Vol. 34 (1995), p.1119.

[9] M. Iire: Chem. Rev. Vol. 100 (2000), p.1685.

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

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

[12] M Irie, O Miyatake, K Uchida and T Eriguchi: J. Am. Chem. Soc. Vol. 116 (1994), p.9894.

[13] K Uchida, T Ishikawa, M Takeshita and Irie M: Tetrahedron Vol. 54 (1998), p.6627.

[14] S.Z. Pu, G. Liu, L. Shen, and J.K. Xu: Organic Letters Vol. 9 (2007), p.2139.

[15] B.Z. Chen, M.Z. Wang, and H. Tian: Chem. Commun Vol. 3 (2002), p.1060.