Synthesis a New Function Materials and Photochromic Properties of Diarylethene Bearing a Naphthalene and Isoxazole Moiety

Abstract:

A new photochromic diarylethene compound 1-(2-methylnaphthyl)-2-(3, 5-dimethyl-4-isoxazolyl)perfluorocyclopentene (1o), was synthesized and its photochromic and fluorescent properties were investigated. Diarylethene 1o changed the color from colorless to yellow upon irraditation with 297 nm UV light, which the absorption maxima were observed at 446 nm in hexane solution. The kinetic experiments indicated that the cyclization/cycloreversion process of the compound was determined to be the zeroth/first order reaction in hexane solution. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light and its closed-ring isomer showed weak fluorescence

• Periodical: Applied Mechanics and Materials (Volume 164)
• Pages: 243-246
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.164.243
• Online since: April 2012
• Authors: Ren Jie Wang, Shi Qiang Cui, Shou Zhi Pu
• Keywords: Diarylethene, Fluorescence, Isoxazole, Naphthalene, Photochromism

References

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

[2] C. Yun, J. You, J. Kim, J. Huh and E. Kim: J. Photochem. Photobiol. C Vol. 10 (2009), p.111.

[3] T. Tsujioka and M. Irie: J. Photochem. Photobiol. C Vol. 11 (2010), p.1.

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

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

[6] F. Buchholtz, A. Zelichenok and V. Krongauz: Macromolecules, Vol. 26 (1993), p.906.

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

[8] M. Morimoto and M. Irie: Chem. Commun. 2005, p.3895.

[9] X.C. Li and H. Tian: Tetrahedron Lett. Vol. 46 (2005), p.5409.

[10] L. Giordano, T.M. Jovin, M. Irie and E.A. Jares-Erijman: J. Am. Chem. Soc. Vol. 124 (2002), p.7481.

[11] S. Kobatake, K. Shibata, K. Uchida and M. Irie: J. Am. Chem. Soc. Vol. 122 (2000), p.12135.

[12] S. Kobatake, M. Yamada, T. Yamada and M. Irie: J. Am. Chem. Soc. Vol. 121 (1999), p.8450.

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

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

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

[16] K. Uchida, S. Nakamura and M. Irie: Res. Chem. Intermed. Vol. 21 (1995), p.861.

[17] R.J. Wang, S.Z. Pu, G. Liu, W.J. Liu and H.Y. Xia: Tetra. Lett. Vol. 52 (2011), p.3306.

[18] S.Z. Pu, M. Li, G. Liu and Z.G. Le: Aust. J. Chem. Vol. 62 (2009), p.464.

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