A New Photochromic Diarylethene for Reversible Molecule Switching Properties Based on Pyrrole and Thiophene

Abstract:

A new unsymmetrical photochromic diarylethene bearing a pyrrole and a thiophene aryl unit 1-(5-cyan-1,2-dimethylpyrrole)-2-(5-aldehyde-2-butylthiophene) perfluorocyclopentene(1a) has been synthesized. Its properties, including photochromism and kinetics were investigated in detail. It underwent reversible cyclization and cycloreversion reactions upon alternating with UV and visible light both in solution and in PMMA film. The results showed that this compound exhibited reversible photochromism, changing from colorless to blue upon irradiation with UV light, in which absorption maximum were observed at 649 nm and 583 nm in solution and PMMA amorphous film, respectively. This new photochromic system also exhibited remarkable reaction kinetics in hexane solution.

• Periodical: Advanced Materials Research (Volumes 284-286)
• Pages: 2239-2242
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.284-286.2239
• Online since: July 2011
• Authors: Shang Hua He, Gang Liu, Ren Jie Wang
• Keywords: Dairylethene, Optical Recording, Photochromism, Reaction Kinetics

References

[1] H.Durr and H.Bouas-Laurent: Photochromism molecules and Systems (Elsevier, Amsterdam 1990).

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

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

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

[5] F. V. Traven, Y. A. Bochkov, M. M. Krayushkin, N. V. Yarovenko, V. B Nabatov, M. S. Dolotov, A. V. Barachevsky and P. I. Beletskaya: Org. Lett. Vol. 10 (2008), p.1319.

DOI: 10.1021/ol800223g

[6] Y Chen, X. D Zeng, N. Xie and Z Y. Dang: J. Org. Chem. Vol. 70 (2005), p.5001.

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

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

[9] Y. Moriyama, K. Matsua, N. Tanifuji and M. Irie: Org. Lett. Vol. 7 (2005), p.3315.

[10] T. Yamaguchi and M. Irie: J. Org. Chem. Vol. 70 (2005), p.10323.

[11] K. Yagi and M. Irie: Bull. Chem. Soc. Jpn. Vol. 76 (2003), p.1625.

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

[13] S. Takami and M. Irie: Tetrahedron Elsevier B. V. Netherlands Vol. 60 (2004), p.6155.

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

[15] T. A. Bens, J. Ern, K. Kuldova, P. H. Trommsdorff and C. Kryschi: J. Lnmin. Papers Vol. 94 (2001), p.51.

[16] J. Ern, T. A. Bens, D. H. Martin, S. Mukamel, D. Schmid, S. Tretiak, E. T. Siper and C. Kryschi: Chem. Phys Papers Vol. 246 (1999), p.115.

DOI: 10.1016/s0301-0104(99)00183-4

[17] S. Z. Pu, M. Li, C. B. Fan, G. Liu and L. Shen: J. Mol. Struct. Vol. 919 (2009), p.100.