Synthesis and Properties of 1-(2-methyl-5-chloro-3-thienyl)-2-(2-trifluoromethylphenyl) perfluorocyclopentene

Abstract:

A novel photochromic diarylethene based on thiophene and a six-membered aryl moieties 1-(2-methyl-5-chloro-3-thienyl)-2-(2-trifluoromethylphenyl) perfluorocyclopentene has been synthesized. At the same time, its photochromic properties and fluorescence switch were investigated in detail. The results showed that this compound exhibited reversible photochromism, undergoing reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light in PMMA film. The fluorescence intensity of diarylethene decreased along with the photochromism from open-ring isomer to closed-ring isomer upon irradiation with 254 nm UV light in PMMA. The fluorescence intensity decreases along with the increase of solution concentration.

• Periodical: Advanced Materials Research (Volume 830)
• Pages: 290-293
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.830.290
• Online since: October 2013
• Authors: Shui Jun Xia, Hai Chang Ding, Gang Liu*
• Keywords: Diarylethene, Fluorescence, Photochromic

References

[1] H. Dürr and H. Bouas-Laurent: Photochromism: Molecules and Systems. Elsevier: Amsterdam, (2003).

[2] B.L. Ed. Feringa: Molecular Switches. Wiley-VCH: Wein-heim, (2001).

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

[4] M. Irie, T. Fukaminato, T. Sasaki, N. Tamai and T. Kawai: Nature. Vol. 420 (2002), p.759.

DOI: 10.1038/420759a

[5] K. Matsuda and M. Irie: Chem. Eur. J. Vol. 7 (2001), p.3466.

[6] M. Morimoto, S. Kobatake and M. Irie: J. Am. Chem. Soc. Vol. 125 (2003), p.11080.

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

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

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

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

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

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

[13] M. Takeshita, M. Ogawa, M. Keisuke and T. Yamato: J. Phys. Org. Chem. Vol. 16 (2003), p.148.

[14] K. Uchida, S. Nakamura and M. Irie: Res. Chem Intermediat. Vol. 21 (1995), p.86.

[15] S.Z. Pu, T.S. Yang, G.Z. Li, J.K. Xu and B. Chen: Tetrahedron Lett. Vol. 47 (2006), p.3167.

[16] T. Norsten and N. Branda: J. Am. Chem. Soc. Vol. 123 (2001), p.1784.