Synthesis and Properties of a Novel Photochromic Diarylethene Bearing Methyl Group

Abstract:

A new unsymmetrical photochromic diarylethene 1-(2,4-dimethyl-3-isoxazol)-2-[2-methyl-5-(2-methyl)-3-thienyl]perfluorocyclopentene (1a) has been synthesized. Its photochromic properties in solution and PMMA film were investigated. Diarylethene 1a changed the color from colorless to pink upon irradiation with 297 nm UV light, in which absorption maxima were observed at 518 nm in hexane and at 527 nm in PMMA film, respectively. In hexane solution, the open-ring isomer of the diarylethene 1 exhibited relatively fluorescence at 386 nm when excited at 309 nm.

• Periodical: Advanced Materials Research (Volumes 393-395)
• Pages: 358-361
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.393-395.358
• Online since: November 2011
• Authors: Zhi Peng Tong, Shou Zhi Pu, Shi Qiang Cui
• Keywords: Diarylethene, Fluorescence Switching, Photochromism

References

[1] H. Durr, L. Bouas: H. Photochromism: Molecules and Systems ( Elsevier Publications, New York 2003).

[2] J.C. Crano, R.J. Guglielmetti, in: Organic Photochromic and Thermochromic Compounds, edited by Plenum Publications, New York (1999), in press.

[3] H. Durr, L. Bouas: H. Photochromism: Molecules and Systems ( Elsevier Publications, New York 1990).

[4] S.L. Gilat, S.H. Kawai and J.M. Lehn: J. Chem. Soc. Chem. Commun. (1993), p.1439.

[5] S.L. Gilat, S.H. Kawai and J.M. Lehn: Chem. —Eur. J. Forum Vol. 1(1995), p.275.

[6] M. Irie and M.J. Mohri: Org. Chem. Forum Vol. 53 (1988), p.803.

[7] M. Irie and K.J. Sayo: Phys. Chem. Forum Vol. 96 (1992), p.7671.

[8] M. Irie: Chem. ReV. Forum Vol. 100 (2000), p.1685.

[9] M. Irie and K. Bull. Uchida: Chem. Soc. Jpn. Forum Vol. 71 (1998), p.985.

[10] M. Irie, T. Lifka, S. Kobatake and N.J. Kato: Am. Chem. Soc. Forum Vol. 122 (2000), p.4871.

[11] H. Miyasaka, T. Nobuto, A. Itaya, N. Tamai and M. Irie: Chem. Phys. Lett. Forum Vol. 269 (1997), p.281.

[12] S. Kobatake and M. Irie: Bull. Chem. Soc. Jpn. Forum Vol. 77 (2004), p.195.

[13] T. Kawai, N. Fukuda, D. Gröschl, S. Kobatake and M. Irie: Jpn. J. Appl. Phys. Forum Vol. 38 (1999), p.1194.

[14] E. Kim, Y. Choi and M. Lee: Macromolecules. Forum Vol. 32 (1999), p.4855.

[15] H. Nakashima and M. Irie: Macromol. Chem. Phys. Forum Vol. 200 (1999), p.683.

[16] M. Irie: Jpn. J. Appl. Phys. Forum Vol. 28 (1989), p.215.

[17] T. Tsujioka, M. Kume and M. Irie: Jpn. J. Appl. Phys. Forum Vol. 34 (1995), p.6439.

[18] M. Takeshita, K. Uchida and M. Irie: Chem. Commun. (1996), p.1807.

[19] K. Matsuda and M. Irie: J. Am. Chem. Soc. Forum Vol. 122 (2000), p.7195.

[20] K. Matsuda, M. Matsuo and M. Irie: J. Org. Chem. Forum Vol. 66 (2001), p.8799.

[21] S. Kawata and Y. Kawata: Chem. ReV. Forum Vol. 100 (2000), p.1777.

[22] M. Irie, S. Kobatake and M. Horichi: Science. Forum Vol. 291 (2001), p.1769.

[23] S. Kobatake, S. Takami, H. Muto, T. Ishikawa and M. Irie: Nature. Forum Vol. 446 (2007), p.778.

[24] A. Spangenberg, R. Métivier, J. Gonzalez, K. Nakatani, P. Yu, M. Giraud, A. Léaustic, R. Guillot, T. Uwada and T. i Asahi: Adv. Mater. Vol. 21 (2009), p.309.

DOI: 10.1002/adma.200801578

[25] Z.X. Li, L.Y. Liao, S. Wei, C. Xu, Z. Chao, C. Fang and C. Yan: J. Phys. Chem. C. Vol. 112 (2008), p.5190.

[26] K. Kasatani, S. Kambe and M. Irie: J. Photoch. Photobiol. A. Vol. 122 (1999), p.11.

[27] B. Chen, M. Wang, Y. Wu and H. Tian: Chem. Commun. (2002), p.1060.

[28] H. Tian, B.Z. Chen, H.Y. Tu and K. Müllen: Adv. Mater. Vol. 14 (2002), p.918.