Synthesis, Photochromism Properties of a Hybrid Diarylethene Based on Hydroxyl Group

Abstract:

A novel unsymmetrical diarylethene derivative 1-[2-methyl-5-(3-trifluoromethylphenyl)-3-thienyl]-2-[2-methyl-5-(4-hydroxylphenyl)-3-thienyl]hexafluorocyclopentene (1a) was successfully synthesized. The properties of the compound, including photochromic and fluorescence properties of the diarylethene were also investigated systematically. The results showed that this compound exhibited reversible photochromism, undergoing reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light both in solution and in PMMA film, and its absorption maxima were observed at 593 nm in methanol and at 598 nm in PMMA amorphous film, respectively, upon irradiation with 297 nm UV light. In methanol solution, the open-ring isomer of the diarylethene 1 exhibited relatively fluorescence at 569 nm when excited at 360 nm.

• Periodical: Advanced Materials Research (Volumes 393-395)
• Pages: 385-388
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.393-395.385
• Online since: November 2011
• Authors: Duo Hua Jiang, Wei Jun Liu, Shi Qiang Cui, Gang Liu
• Keywords: Diarylethene, Fluorescence, Photochromism

References

[1] M. Irie: Photo-reactive Materials for Ultrahigh-density Optical Memory (Elsevier Science Ltd. Europe 1994).

[2] B.L. Feringa: Molecular Switches (Wiley-VCH: Weinheim, Germany 2001).

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

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

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

DOI: 10.1038/420759a

[6] H. Durr and H. Bouus-Laurent, Photochromism: Molecules and Systems (Elsevier, Amsterdam The Netherlands, 1990).

[7] K. Matsuda and M. Irie: J. Photochem. Photobiol. C. Vol. 5 (2004), p.169.

[8] C. Bertarelli, A. Bianco, F. D'Amore, M.C. Gallazzi and G. Zerbi: Adv. Funct. Mater. Vol. 14 (2004), p.357.

[9] E. Kim, Y. -K. Choi, M. -H. Lee: Macromolecules, Vol. 32 (1999), p.4855.

[10] G. Guirado, C. Coudret, M. Hliwa and J. -P. Launay: J. Phys. Chem. B Vol. 109 (2005), p.17445.

[11] W.R. Browne, J.J.D. de Jong, T. Kudernac, M. Walko, L.N. Lucas, K. Uchida, J.H. van Esch and B.L. Feringa: Chem. Eur. J. Vol. 11 (2005), p.6414.

DOI: 10.1002/chem.200500162

[12] W.R. Browne, J.J.D. de Jong, T. Kudernac, M. Walko, L.N. Lucas, K. Uchida, J.H. van Esch and B.L. Feringa: Chem. Eur. J. Vol. 11 (2005), p.6430.

DOI: 10.1002/chem.200500163

[13] T. Okuyama, Y. Tani, K. Miyake and Y. Yokoyama: J. Org. Chem. Vol. 72 (2007), p.1634.

[14] Y. Tani, T. Ubukata, Y. Yokoyama and Y. Yokoyama: J. Org. Chem. Vol. 72 (2007), p.1639.

[15] K. Matsuda, S. Yamamoto and M. Irie: Tetrahedron Lett. Vol. 42 (2001), p.7291.

[16] C.C. Corredor, Z. -L. Huang and K.D. Belfield: Adv. Mater. Vol. 18 (2006), p.2910.

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

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

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

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

[21] J.J. Zhang, W.J. Tan, X.L. Meng and H. Tian: J. Mater. Chem. Vol. 19 (2009), p.5726.

[22] H. Tian, and S. Wang, Chem. Commun. (2007), p.781.

[23] Y.L. Feng, Y.L. Yan, S. Wang, W.H. Zhu, S.X. Qian and H. Tian: J. Mater. Chem. Vol. 16 (2006), p.3685.

[24] K. Higashiguchi, K. Matsuda, N. Tanifuji and M. Irie: J. Am. Chem. Soc. Vol. 127 (2005), p.8922.

[25] S. Z Pu, J.K. Xu, L. Shen, Q. Xiao, T.S. Yang and G. Liu: Tetrahedron Lett. Vol. 46 (2005), p.871.

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

[27] T.B. Norsten and N.R. Branda: J. Am. Chem. Soc. Vol. 123 (2001), p.1784.