Synthesis and Properties Study of 1-(2,4-dimethoxyl-5-pyrimidinyl)-2-[2-methyl-5-(4-n-pentylbenzene)-3-thienyl] Perfluorocyclopentene

Abstract:

A novel photochromic diarylethene based on a six-membered pyrimidine moiety 1-(2,4-dimethoxyl-5-pyrimidinyl)-2-[2-methyl-5-(4-n-pentylbenzene)-3-thienyl] perfluorocyclopent-ene has been synthesized. Its properties, including photochromic behavior and fluorescent properties, have been investigated. The compounds exhibited remarkable photochromism, changing from colorless to red after irradiation with UV light both in solution and in PMMA film. The fluorescence had a remarkable initial increase with subsequent dramatic decrease with increasing concentration. The results indicated that the pyrimidine moiety played a very important role during the process of photoisomerization reactions.

• Periodical: Advanced Materials Research (Volume 952)
• Pages: 75-78
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.952.75
• Online since: May 2014
• Authors: Jing Jing Liu, Hong Jing Jia, Shou Zhi Pu*
• Keywords: Diarylethene, Fluorescence, Photochromism, Pyrimidine

References

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

[2] S. Kawata: Chem. Rev. Vol. 100 (2000), p.1777.

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

[4] S.H. Chen, H.M.P. Chen, Y. Geng, D.J. Stephen, K.L. Marshall and T.N. Blanton: Adv. Mater. Vol. 15 (2003), p.1061.

[5] K. Uchida, A. Takata, M. Saito, A. Murakami, S. Nakamura and M. Irie: Adv. Mater. Vol. 15 (2003), p.785.

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

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

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

[9] K. Uchida, T. shikawa, M. Takeshita and M. Irie: Tetrahedron Vol. 54 (1998), p.6627.

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

[11] S.Z. Pu, H. Li, G. Liu and W.J. Liu: Tetrahedron Lett. Vol. 5 (2010), p.3575.

[12] K. Uchida, T. Matsuoka, K. Sayo, M. Iwamoto, S. Hayashi and M. Irie: Chem. Lett. Vol. 8 (1999), p.835.

[13] Z.X. Li, L.Y. Liao,W. Sun, C.H. Xu, C. Zhang, C.J. Fang and C.H. Yan: J. Phys. Chem. C. Vol. 112 (2008), p.5190.

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

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

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