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

Abstract:

A novel unsymmetrical diarylethene derivative 1-[2-methyl-5-(4-pyridine)-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 absorption maxima of this compound were observed at 606 nm in methanol and at 612 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 499 nm when excited at 414 nm. This new photochromic compound also exhibited remarkable optical storage character.

• Periodical: Advanced Materials Research (Volumes 399-401)
• Pages: 1180-1183
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.399-401.1180
• Online since: November 2011
• Authors: Duo Hua Jiang, Gang Liu, Wei Jun Liu, Cong Bin Fan
• Keywords: Diarylethene, Fluorescence, Optical Storage, Photochromism

References

[1] M. Irie: Photo-reactive Materials for Ultrahigh-density Optical Memory (Elsevier, Amsterdam 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 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 and 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.

[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, 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] M. Liu, S.Z. Pu, G. Liu, C.B. Fan and S.Q. Cui: POEM Vol. 276 (2011), p.1742.

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

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

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

[29] B.L. Yao, Y.L. Wang and M. Lei: Optics Express Vol. 13 (2005), p.20.