Synthesis and Properties of a Novel Material Chemistry Unsymmetrical Material, Diarylethene with Cyano

Abstract:

A unsymmetrical photochromic diarylethene, 1-{[2-methyl-5-(1,3-dioxolane)-3-thienyl]} -2-[2-methyl-5-(4-cyanophenyl)-3-thienyl]perfluorocyclopentene(1a),was synthesized, and its optoelectronic properties were also investigated in detail. The results showed that this compound exhibited reversible photochromism, changing from colorless to blue violet after irradiation with UV light both in solution and in PMMA amorphous film.The diarylethene exhibited a fluorescence switches along with the photochromism from open-ring isomers to closed-ring isomers. When irradiated by UV light, the photocyclization reaction was occurred and the emission intensity of the diarylethene decreased significantly, due to producing the non-fluorescence closed-ring isomers. The back irradiation by appropriate wavelength visible light regenerated its open-ring isomers and recovered the original emission intensity

• Periodical: Applied Mechanics and Materials (Volume 164)
• Pages: 150-153
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.164.150
• Online since: April 2012
• Authors: Wei Wei Geng, Cong Bin Fan, Shou Zhi Pu
• Keywords: Diarylethene, Fluorescence Switching, Optical Recording Storage, Photochromism

References

[1] D. H. Waldeck: Chem. Rev. Vol. 91 (1991), p.415.

[2] G. S. Kumar and D. C. Neckers: Chem. Rev. Vol . 89 (1989), p. (1915).

[3] H. G. Heller and S. Oliver: J. Chem. Soc. Vol. 1 (1981), p.197.

[4] Y. Yokoyama: Chem. Rev. Vol. 100 (2000), p.1717.

[5] M. V. Alfimov, O. A. Fedorova and S. P. Gromov: Journal of Photochemistry and Photobiology A: Chem. Vol. 158 (2003), p.183.

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

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

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

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

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

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

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

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

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

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

[16] K. Matsuda and M. Irie: Journal of Photochemistry and Photobiology C: Photochemistry Rev. Vol. 5 (2004), p.169.

[17] M. Irie and K. Uchida: Chem. Soc. Vol. 71 (1998), p.9852.

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

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

[20] B. L. Yao, Y. L. Wang, M. Lei, N. Menke and G. F. Chen. Opt. Express. Vol. 13 (2005), p.20.

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