Photochromism and Optical Recording of a Novel Diarylethene Bearing Phenanthrene Unit

Abstract:

Photochromic molecules are part of a large class of materials in which light stimulus not only induces a color variation but also affects other physicochemical properties. In the paper, an asymmetrical photochromic diarylethene, 1-(2,4-dimethyl-3-thiazole)-2-[2-methyl-5-(10-phenanthrenyl)-3-thienyPerfluorocyclopentene was synthesized and its photochromic and fluorescent properties were systematically investigated. The compound exhibited remarkable photochromic, changing from colorless to OrangeRed after irradiation with UV light both in solution and in PMMA film. In addition, its fluorescence property was also discussed. When irradiation with UV light, the fluorescence intensity declined remarkably. The results showed that the diarylethene exhibited a relatively strong fluorescence switch along with the photochromism from open-ring isomer to closed-ring isomer. Using this diarylethene 1a as optical storage was performed successfully.

• Periodical: Advanced Materials Research (Volume 763)
• Pages: 79-83
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.763.79
• Online since: September 2013
• Authors: Xue Li, Cong Bin Fan, Gang Liu
• Keywords: Diarylethene, Fluorescence, Optical Recording, Phenanthrene, Photochromism

References

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

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

[3] H. Dürr, H. Bouas-Laurent: Photochromism: Molecules and Systems (Elsevier, Amsterdam 1990).

[4] M. Irie, M. Mohri: J. Org. Chem. Vol. 53 (1988), p.803.

[5] T. Kaieda, S. Kobatake, H. Miyasaka, M. Murakami, N Iwai, Y.I. Nagata, A. Itaya and M. Irie: J. Am. Chem. Soc. Vol. 124 (2002), p. (2015).

DOI: 10.1021/ja0115722

[6] S.Z. Pu, C.B. Fan, W.J. Miao and G. Liu: Tetrahedron. Vol. 64 (2008), p.9464.

[7] S.Z. Pu, P.J. Yan, G. Liu, W.J. Miao and W.J. Liu: Tetrahedron Lett. Vol. 52 (2011), p.143.

[8] R.J. Wang, S.Z. Pu, G. Liu, S.Q. Cui and W.J. Liu: Tetrahedron Lett. Vol. 53 (2012), p.320.

[9] A.J. Myles, N.R. Branda: J. Am. Chem. Soc. Vol. 123 (2001), p.177.

[10] K. Matsuda, M. Irie: J. Photoch. Photobiol. C. Vol. 5 (2004), p.169.

[11] X. Li, W.J. Liu and G. Liu: Advanced Materials Research. Vol. 58 (2012), p.130.

[12] X. Li, C.B. Fan and G. Liu: Applied Mechanics and Materials. Vol. 164 (2012), p.255.

[13] S. Z. Pu, H.H. Tang, B. Chen, J.K. Xu and W.H. Huang: Mater. Lett. Elsevier. Vol. 60 (2006), p.3553.

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

[15] H. Tian, B.Z. Chen, H.Y. Tu and K. Müllen: Adv. Mater. Vol. 14 (2002), p.918.