Study on Photochromic Perfluorocyclopetene Containing Six-Numbered Unit as Optical Recording Materials

Abstract:

A reversible molecule switching of symmetrical photochromic diarylethene 1,2-bis methyl phenyl perfluorocyclopentene has been synthesized and its photochromic and simulated molecule structure were also investigated. The compound exhibited photochromism both in solution and PMMA film but no photochromism in solid state. In hexane, the open-ring isomer of the diarylethene 1o showing an absorption peak at 308 nm. Upon irradiation with 313 nm light, a new absorption band in the visible region centered at 595 nm emerged to form closed isomer 1c. This compound can be used as optical recording materials.

• Periodical: Applied Mechanics and Materials (Volume 327)
• Pages: 58-62
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.327.58
• Online since: June 2013
• Authors: Hai Bo Wang, Cong Bin Fan, Gang Liu
• Keywords: Optical Recording, Photochromic Materials, Photochromism, Structure

References

[1] H. Tian, Y.L. Feng, J. Mater. Chem. vol. 18 (2008) p.1617

[2] A.C. Whalley, M.L. Steigerwald, X. Guo, C. Nuckolls, J. Am. Chem. Soc. vol 129 (2007), p.12590

[3] Q. Zou, X. Li, J. J. Zhang, J. Zhou, B. B. Sun, and H. Tian, Chem. Commun., vol 48 (2012), p (2095)

[4] S. Z. Pu, D. H. Jiang, W. J. Liu, G. Liu, and S. Q. Cui, J. Mater. Chem., vol 22 (2012), p.3517

[5] T. Tsujioka, T. Sasa, Y. Kakihara, Org. Electr., vol. 13 (2012), p.681

[6] C. B. Fan, P. Yang, X. M. Wang, G. Liu, X. X. Jiang, H. Z. Chen, X. T. Tao, M. Wang, M. H. Jiang, Sol. Energ. Mat. Sol. C., vol. 95 (2011), p.992

[7] H. Tian, S. J. Yang, Chem. Soc. Rev. vol 33 (2004), p.85

[8] T. Fukaminato, T. Sasaki, T. Kawai, N. Tamai, and M. Irie, J. Am. Chem. Soc. vol 126 (2004), p.14843

[9] C. Bertarelli, A. Bianco, Franco D'Amore, M. C. Gallazzi, and G. Zerbi, Adv. Funct. Mater. vol 14 (2004), p.357

[10] B. M. Neilson and C. W. Bielawski, J. Am. Chem. Soc. vol 134 (2012), p.12693

[11] Y. Li and Q. Li, Org. Lett., vol 14 (2012), p.4362

[12] G. Liu, S. Pu, and R. Wang, Org. Lett.,  vol 15 (2013), p.980

[13] K A. Muszkat, Top Curr Chem, vol 88 (1980), p.89

[14] Woodward RB, Hoffmann R. The conservation of orbital symmetry.Weinheim, Germany: Verlag Chemie; GmbH, (1970)

[15] M. Morimoto, M. Irie, Chem. Eur. J. vol 12 (2006), p.4275

[16] V. Ramamurthy, K. Venkatesan, Chem. Rev. vol 87 (1987), p.433

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

[18] L. Ordronneau, H. Nitadori, I. Ledoux, A. Singh, J.A.G. Williams, M. Akita, V. Guerchais, and H. L. Bozec, Inorg. Chem., vol 51 (2012), p.5627

DOI: 10.1021/ic2025457

[19] S.Z Pu, T.S. Yang, J.K. Xu, B. Chen. Tetrahedron Lett. vol 47 (2006), p.6473

[20] S.Z Pu, T.S. Yang, B.l. Yao, Y.l. Wang, M. Lei, J.k. Xu. Mater. Lett. vol 61 (2007), p.855

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

[22] K. Kasatani, S. Kambe, M. Irie, J. Photochem. Photobiol. A: Chem. vol 122 (1999), P 11