Efficient Synthesis, Photochromism and Application of a Photochromic Diarylethene Bearing a Benzene Unit

Abstract:

A novel photochromic diarylethene bearing a six-membered aryl unit, 1-[2-methyl-5-(3-fluorophenyl)-3-thienyl]-2-(2-methoxylphenyl)perfluorocyclopentene (1o), was synthesized and its photochromic properties, fluorescence switch and optical recording were investigated in detail. This compound exhibited remarkable photochromism, changing from colorless to blue after irradiation with 297 nm UV light both in solution and in PMMA film, respectively. The new diarylethene also exhibited excellent fluorescence intensity and fluorescence switches by photoirradiation in hexane solution. Finally, photo-mode rewritable optical storage using 1o was performed. The images demonstrated that the compound as optical storage material was very sensitive responding to 633 nm recording laser, and the recorded-signals were provided with high S/N ratio.

• Periodical: Advanced Materials Research (Volumes 295-297)
• Pages: 1038-1041
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.295-297.1038
• Online since: July 2011
• Authors: Ren Jie Wang, Gang Liu, Hong Ying Xia, Shi Qiang Cui
• Keywords: Diarylethene, Fluorescence, Optical Storage, Photochromism

References

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

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

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

[4] K. Matsuda, M. Irie: J. Photochem. C: Photobio. Vol. 5 (2004), p.169

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

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

[7] X.D. Deng, L.S. Liebeskind: J. Am. Chem. Soc. Vol. 123 (2001), p.7703

[8] K. Uchida, T. Ishikawa, M. Takeshita, M. Irie: Tetrahedron. Vol. 54 (1998), p.6627

[9] S. Takami, M. Irie, Tetrahedron. Vol. 60 (2004), p.6155

[10] S.Z. Pu, H. Li, G. Liu, W.J. Liu: Tetrahedron Lett. Vol. 51 (2010), p.3575

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

[12] K. Yagi, C.F. Soong, M. Irie: J. Org. Chem. Vol. 66 (2001), p.5419

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

[14] T. Yamaguchi, M. Irie: Tetrahedron Lett. Vol. 47 (2006), p.1267

[15] S.Z. Pu, T.S. Yang, J.K. Xu, B. Chen: Tetrahedron Lett. Vol. 47 (2006), p.6473

[16] T.S. Yang, S.Z. Pu, B. Chen, J.K. Xu: Can. J. Chem. Vol. 85 (2007), p.12

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

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

[19] K. Kasatani, S. Kambe, M. Irie: J. Photoch. Photobiol. A. Chem. Vol. 122 (1999), p.11

[20] C.B. Fan, S.Z. Pu, G. Liu, and T.S. Yang: J. Photoch. Photobiol. A. Vol. 194 (2008), p.333

[21] T. Fukaminato, T. Kawai, S. Kobatake, M. Irie: J. Phys. Chem. B. Vol. 107(33) (2003), p.8372

[22] S.Z. Pu, T.S. Yang, B.L. Yao, Y.L. Wang, M. Lei, J.K. Xu: Mater. Lett. Vol. 61 (2007), p.855.