Research on Photochromic Materials with Synthesis and Properties of 1-(2-Methyl-3-Benzothiophene)-2-[2-Methyl-5-(3-Cyanophenyl)-3-Thienyl]Perfluorocyclopentene

Article Preview

Abstract:

An asymmetrical photochromic diarylethene1-(2-Methyl-3-benzothiophene)-2-[2-methyl-5-(3-cyanophenyl)-3-thienyl] perfluorocyclopentene (1o) was synthesized and its phtochromic, fluorescent properties in both solution and PMMA films were investigated in detail. This compound exhibited remarkable photochromism, upon irradiation with 297 nm UV light, the colorless solution of 1o turned to violet with a new visible absorption band centered at 535 nm (ε = 1.08 × 104 L mol-1 cm-1) attributable to the closed-ring isomer 1c. The emission intensity of diarylethene 1o in a photostationary state was quenched to ca. 32% in hexane and 43% in PMMA film.

You might also be interested in these eBooks

Info:

Periodical:

Pages:

95-98

Citation:

Online since:

October 2014

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2014 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

* - Corresponding Author

[1] P. Rudolf, J. Buback and J. Aulbach: J. Am. Chem. Soc. Vol. 132 (2010), p.15213.

Google Scholar

[2] S. J. Sarma and P. B. Jones: J. Org. Chem. Vol. 75 (2010), p.3806.

Google Scholar

[3] S. Dong, H. Hwang, X. Shi, L. Holloway and H. Yu: Chem. Res. Toxicol. Vol. 13 (2000), p.585.

Google Scholar

[4] Y. Hou, X. Li, Q. Zhao, X. Quan and G. Chen: Environ. Sci. Technol. Vol. 44 (2010), p.5098.

Google Scholar

[5] M. Faustini, L. Nicole, C. Boissire, P. Innocenzi, C. Sanchez and D. Grosso: Chem. Mater. Vol. 22 (2010), p.4406.

Google Scholar

[6] D. J. Kang and B. S. Bae: Acc. Chem. Res. Vol. 40 (2007), p.903.

Google Scholar

[7] W. Tan, Q. Zhang, J. Zhang and H. Tian: Org. Lett. Vol. 11 (2009), p.161.

Google Scholar

[8] K. Morinaka, T. Ubukata and Y. Yokoyama: Org. Lett. Vol. 11 (2009), p.3890.

Google Scholar

[9] A. J. Myles, B. Gorodetsky and N. R. Branda: Adv. Mater. Vol. 16 (2004), p.922.

Google Scholar

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

Google Scholar

[11] K. Mastuda and M. Irie:J. Am. Chem. Soc. Vol. 122 (2000), p.7195.

Google Scholar

[12] T. Kawai and Y. Nakashima: Adv. Mater. Vol. 17 (2005), p.309.

Google Scholar

[13] V. Lemieux, S. Gauthier and N. R: Branda, Angew. Chem., Int. Ed. Vol. 45 (2006), p.6820.

Google Scholar

[14] T. Hirose, K. Matsuda and M. Irie: J. Org. Chem. Vol. 71 (2006), p.7499.

Google Scholar

[15] H. Tian and Y. Feng: J. Mater. Chem. Vol. 18 (2008), p.1617.

Google Scholar

[16] H.H. Liu and Y. Chen: J. Mater. Chem. Vol. 19 (2009), p.706.

Google Scholar

[17] N. Iwasawa, H. Takahagi, K. Ono, K. Fujiib and H. Uekusab: Chem. Commun. Vol. 48 (2012), p.7477.

Google Scholar

[18] M. Taguchi, T. Nakagawa, T. Nakashima and T. Kawai: J. Mater. Chem. Vol. 21 (2011), p.17425.

Google Scholar

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

Google Scholar

[20] 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.

Google Scholar

[21] S.Z. Pu, C.B. Fan, W.J. Miao, G. Liu: Tetrahedron. Vol. 64 (2008), p.94649.

Google Scholar

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

Google Scholar

[23] S.Z. Pu, C.B. Fan, W.J. Miao, G. Liu: Dyes. Pigm. Vol. 84 (2010), p.25.

Google Scholar

[24] K. Kasatani, S. Kambe, M. Irie: J. Photochem. Photobiol. A. Vol. 122 (1999), p.22.

Google Scholar

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

DOI: 10.1038/420759a

Google Scholar

[26] S.Z. Xiao, T. Yi, Y.F. Zhou, Q. Zhao, F.Y. Li and C.H. Huang: Tetrahedron. Vol. 62 (2006), p.10072.

Google Scholar