Photochromism, Kinetics and Fluorescence of 1-(2-methyl-3-benzofuranyl)-2-[2-methyl-5-(4-cyanophenyl)-3-thienyl]perfluorocyclopentene

Abstract:

An unsymmetrical photochromic diarylethene compound, 1-(2-methyl-3-benzofuranyl)-2-[2-methyl-5-(4-cyanophenyl)-3-thienyperfluorocyclopentene was synthesized, and its photochromic properties, kinetics of the photochromic cyclization/cycloreversion and fluorescence were investigated in detail. The compound exhibited good photochromism, changing from colorless to red after irradiation with 297 nm UV light, in which absorption maxima were observed at 530 nm in hexane solution. Simultaneously, cyclization/cycloreversion kinetics of this diarylethene was researched. The open-ring isomer of the diarylethene exhibited relatively strong fluorescence at 377 nm in hexane solution (2 × 10^-5 mol L^-1), when excited at 327 nm. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light. The fluorescence spectra of the diarylethene are depended on the concentration.

• Periodical: Advanced Materials Research (Volume 886)
• Pages: 175-178
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.886.175
• Online since: January 2014
• Authors: Dan Dan Xue, Zhi Yuan Sun, Shou Zhi Pu*
• Keywords: Diarylethene, Fluorescence, Kinetic, Photochromism

References

[1] H. Dürr and H. Bouas-Laurent: Photochromism molecules and systems (Elsevier, Amsterdam 1990).

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

[3] Y. Kishimoto, J. Abe: J. Am. Chem. Soc. Vol. 131 (2009), p.4227.

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

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

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

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

[8] S.C. Pang, H. Hyun, S. Lee, D. Jang, M.J. Lee, S.H. Kang and K.H. Ahn: Chem. Commun. Vol. 48 (2012), p.3745.

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

[10] S.Z. Pu, T.S. Yang, J.K. Xu, L. Shen and G. Liu: Tetrahedron Vol. 61 (2005), p.6623.

[11] S. Yamamoto, K. Matsuda and M. Irie: Chem. Eur. J. Vol. 9 (2003), p.4878.

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

[13] K. Morimitsu, K. Shibata, S. Kobatake and M. Irie: J. Org. Chem. Vol. 67 (2002), p.4574.

[14] S.Z. Pu, G. Liu and J.K. Xu: Org. Lett. Vol. 9 (2007), p.2139.

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

[16] B.Z. Chen, M.Z. Wang and H. Tian: Chem. Commun. 2002, p.1060.

[17] T. Fukaminato, T. Kawai, S. Kobatake and M. Irie: J. Phys. Chem. B. Vol. 107 (2003), p.8372.