Photoinduced Anisotropy in a New Diarylethene Bearing Five and Six-Membered Aryl

Abstract:

A new symmetrical photochromic diarylethene, 1-(2-methyl-5-formyl)-2-(2- cyanophenyl) perfluorocyclopentene(1a), was synthesized, and its photochromic properties were investigated in detail. The compound exhibited good photochromism both in solution and in PMMA film with alternating irradiation by UV/VIS light, and the maxima absorption of its closed-ring isomer 1b are 544 and 549 nm, respectively. The photochromism properties of 1a diarylethene show good photochromism in hexane and in PMMA amorphous film. Steady state fluorescence studies indicated that 1a diarylethene is higher fluorescent in the open-ring isomer, but there almost no fluorescence in the closed-ring isomer in PMMA amorphous film. The diarylethene 1a has promising application for photo-switching, fluorescence-switching which can use for data storage.

• Periodical: Advanced Materials Research (Volumes 490-495)
• Pages: 3387-3390
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.490-495.3387
• Online since: March 2012
• Authors: Zhi Peng Tong, Shou Zhi Pu, Shi Qiang Cui
• Keywords: Diarylethene, Fluorescence, Optical Recording, Photochromism

References

[1] J. Fritzsche, Comptes Rendus Acad. Sci. Paris. 69 (1867) 1035-1037.

[2] H. Dürr, H. Bouas-Laurent, Photochromism, Molecules and Systems; Elsevier, Amsterdam, (1990).

[3] M. Irie, Chem. Rev. 100 (2000) 1685-1716.

[4] H. Tian, S. Yang, J. Chem. Soc. Rev. 33 (2004) 85-97.

[5] K. Higashiguchi, K. Matsuda, N. Tanifuji, M. Irie, J. Am. Chem. Soc. 127 (2005) 8922-8923.

[6] V.F. Traven, A.Y. Bochkov, M.M. Krayushkin, V.N. Yarovenko, B.V. Nabatov, S.M. Dolotov, V.A. Barachevsky, I.P. Beletskaya, Org. Lett. 10 (2008) 1319-1322.

DOI: 10.1021/ol800223g

[7] Y. Chen, D.X. Zeng, N. Xie, Y.Z. Dang, J. Org. Chem. 70 (2005) 5001-5005.

[8] T. Fukaminato, T. Sasaki, T. Kawai, N. Tamai, M. Irie, J. Am. Chem. Soc. 126 (2004) 14843–14849.

DOI: 10.1021/ja047169n

[9] S.Z. Pu, F.S. Zhang, J.K. Xu, L. Shen, Q. Xiao, B. Chen, Mater. Lett. 60 (2006) 485-489.

[10] A. Spangenberg, R. Métivier, J. Gonzalez, K. Nakatani, P. Yu, M. Giraud, A. Léaustic, R. Guillot, T. Uwada, T. i Asahi, Adv. Mater. 21 (2009) 309-313.

DOI: 10.1002/adma.200801578

[11] Z.X. Li, L.Y. Liao, S. Wei, C. Xu, Z. Chao, C. Fang , C. Yan, J. Phys. Chem. C. 112 (2008) 5190-5196.

[12] K. Kasatani, S. Kambe and M. Irie, J. Photoch. Photobiol. A. 122 (1999) 11-15.

[13] B. Chen, M. Wang, Y. Wu , H. Tian, Chem. Commun. (2002) 1060-1061.

[14] H. Tian, B.Z. Chen, H.Y. Tu, K. Müllen, Adv. Mater. 14 (2002) 918-923.

[15] T. Fukaminato, T. Kawai, S. Kobatake, M. Irie, J. Phys. Chem. B. 107 (2003) 8372-8377.