Synthesis and Photochromism Studies of 1-(2-Methyl-3-Benzothiophenyl)-2-[2-Methyl-5-(4-Azidomethyl)-3-Thienyl]Perfluorocyclopentene

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Abstract:

An unsymmetrical photochromic diarylethene 1-(2-methyl-3-benzothiophenyl)-2-[2-methyl-5-(4-azidomethyl)-3-thienyperfluorocyclopentene was synthesized, and its optoelectronic properties were also investigated. The results showed that this compound exhibited reversible photochromism, changing from colorless to darkorange after irradiation with UV light in solution. The open-ring isomer of the diarylethene 1o exhibited relatively strong fluorescence at 457 nm in acetonitrile solution (2×10-5 mol L-1) when excited at 287 nm. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light. The electrochemical properties indicated that the oxidation onset and the Eg of the open-ring isomer were lower than the closed-ring isomer.

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81-84

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December 2013

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© 2014 Trans Tech Publications Ltd. All Rights Reserved

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[1] H. Dürr and H. Bouas-Laurent: Photochromism: Molecules and Systems Access Online via Elsevier, (2003).

Google Scholar

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

Google Scholar

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

Google Scholar

[4] S.Z. Pu, T. Yang, J.K. Xu, L. Shen, G. Li, Q. Xiao and B. Chen: Tetrahedron Vol. 61 (2005), p.6623.

Google Scholar

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

Google Scholar

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

Google Scholar

[7] D. Bonifazi, M. Scholl, F. Song, L. Echegoyen, G. Accorsi, N. Armaroli and F. Diederich: Angew. Chem. Int. Ed Vol. 42 (2003), p.4966.

DOI: 10.1002/anie.200352265

Google Scholar

[8] B. Gorodetsky, H. D. Samachetty, R. L. Donkers, M. S. Workentin and N. R. Branda: Angew. Chem. Int. Ed Vol. 43 (2004), p.2812.

DOI: 10.1002/anie.200353029

Google Scholar

[9] 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.

DOI: 10.1002/chem.200500163

Google Scholar

[10] 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

Google Scholar