Synthesis and Photochromic Properties of Diarylethene 1-[2,4-dimethyl-5-thiazolyl]-2-[2-methyl-5-(2-methylphenyl)-3-thienyl]perfluorocyclopentene

Abstract:

A new unsymmetrical photochromic diarylethene, 1-[2,4-dimethyl-5-thiazolyl]-2-[2-methyl-5-(3-4-trifluoromethylphenyl)-3-thienyl] perfluorocyclopentene (1o) was synthesized, and its properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous film, and fluorescence properties were investigated in detail. The results showed the compound exhibited good photochromism in hexane solution and in PMMA amorphous film, the maxima absorption of its closed-ring isomer 1c are 490 nm and 495 nm respectively. The open-ring isomer of the diarylethene 1o exhibited relatively strong fluorescence at 449 nm in hexane solution (2 × 10^-5 mol/L) when excited at 330 nm and at 438 nm in PMMA amorphous film when excited at 280 nm. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light.

• Periodical: Advanced Materials Research (Volume 952)
• Pages: 92-95
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.952.92
• Online since: May 2014
• Authors: Dan Dan Xue, Chun Hong Zheng, Shou Zhi Pu*
• Keywords: Diarylethene, Fluorescence, Photochromism

References

[1] S. Wang, Q. Z . Qi, C.P. Li, G.H. Ding and S.H. Kim: Dyes. Pigm. Vol. 89 (2011), p.188.

[2] S. Kawata and Y. Kawata: Chem. Rev. Vol. 100 (2000), p.1777.

[3] H. Tian and Y.L. Feng: J. Mater. Chem. Vol. 18 (2008), p.1617.

[4] D. Sud, T.B. Norsten and N.R. Branda: Angew. Chem. Int. Ed. Vol. 44 (2005), p (2019).

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

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

[7] H. Tian and Wang S: Chem. Commun. Vol. 8 (2007), p.781.

[8] W.H. Zhu, X.L. Meng, Y.H. Yang, Q. Zhang, Y.S. Xie and H. Tian: Chem. Eur. J. Vol. 16 (2010), p.899.

[9] F. Sun, F.S. Zhang, H.B. Guo, X.H. Zhou, R.J. Wang and F.Q. Zhao: Tetrahedron Vol. 59 (2003), p.7615.

[10] S.L. Gilat, S.H. Kawai and J.M. Lehn: Chem. Eur. J. Vol. 1 (1995), p.275.

[11] T. Fukaminato, M. Tanaka, L. Kuroki and M. Irie: Chem. Commun. 2008, p.3924.

[12] T. Tsujioka, M. Kume and M. Irie: Jpn. J. Appl. Phys. Vol. 35 (1996), p.4353.

[13] G. Liu, T. Zheng, S.Z. Pu, J.K. Xu: Acta Cryst. E. Vol. 62 (2006), p.2877.

[14] C.B. Fan, S.Z. Pu, G. Liu and T.S. Yang: J. Photoch. Photobiol. A. Vol. 12 (2008), p.333.

[15] T.B. Norsten and N.R. Branda: J. Am. Chem. Soc. Vol. 60 (2001), p.1784.