Thermally Irreversible Photochromic Systems. Reversible Photocyclization of 2-(1-Benzothiophen-3-yl)-3-(2 or 3-thienyl)maleimide Derivatives

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Abstract

Non-symmetric diarylethenes that have a 1-benzothiophene ring on one end and a 2-thienyl or 3-thienyl group on the other end of the double bond of maleimide were synthesized in order to study the effects of the substitution position of the thiophene ring on the absorption bands and the reactivities. The open-and closed-ring forms of <i>N</i>-cyanomethyl-2-(2,4-dimethyl-5-phenyl-3-thienyl)-3-(2-methoxy-1-benzothiophen-3-yl)maleimide showed absorption bands at 420 and 563 nm in hexane, respectively. When 3-thienyl was changed to 2-thienyl, the absorption bands of <i>N</i>-cyanomethyl-2-(3,4-dimethyl-5-phenyl-2-thienyl)-3-(2-methoxy-1-benzothiophen-3-yl)maleimide shifted to 448 nm (the open-ring form) and 487 nm (the closed-ring form), respectively. The cyclization and ring-opening quantum yields were also dependent on the substitution position. The cyclization yield decreased from 0.30 to 0.03 by changing the position from 3- to 2-thienyl, while the ring-opening yield increased from 0.03 to 0.13. No absorption spectral change by photoirradiation was observed for <i>N</i>-cyanomethyl-2,3-bis(3,4-dimethyl-5-phenyl-2-thienyl)maleimide, which has two 2-thienyl groups.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 71(5), 1101-1108, 1998-05-15

    The Chemical Society of Japan

References:  15

  • <no title>

    IRIE M.

    Photoreactive Materials for Ultrahigh Optical Density 1, 1994

    Cited by (1)

  • <no title>

    NAKAMURA S.

    J. Org. Chem. 53, 6136, 1988

    Cited by (11)

  • <no title>

    IRIE M.

    J. Org. Chem. 53, 803, 1988

    Cited by (34)

  • <no title>

    UCHIDA K.

    Bull. Chem. Soc. Jpn. 63, 1311, 1990

    Cited by (19)

  • <no title>

    NAKAYAMA Y.

    J.Org.Chem. 55, 2592, 1990

    Cited by (5)

  • <no title>

    HANAZAWA M.

    J. Chem. Soc., Chem. Commun. 1992, 206

    Cited by (9)

  • <no title>

    GILAT S. L.

    Chem. Eur. J. 1, 275, 1995

    Cited by (14)

  • <no title>

    YAMAGUCHI T.

    J.Am.Chem.Soc. 119, 6066, 1997

    Cited by (10)

  • <no title>

    UCHIDA K.

    Chem. Lett. 1995, 969

    Cited by (5)

  • <no title>

    IWATA S.

    J. Org. Chem. 57, 3726, 1992

    Cited by (2)

  • <no title>

    IRIE M.

    J. Org. Chem. 60, 8305, 1995

    Cited by (17)

  • <no title>

    TANIGUCHI H.

    Nippon Kagaku Kaishi 1992, 1138

    Cited by (1)

  • <no title>

    YOKOYAMA Y.

    Nippon Kagaku Kaishi 1992, 998

    Cited by (3)

  • <no title>

    YOKOYAMA Y.

    Synth. Org. Chem. Jpn. 49, 364, 1991

    Cited by (1)

  • <no title>

    IRIE M.

    Tetrahedron 53, 12263, 1997

    DOI  Cited by (3)

Codes

  • NII Article ID (NAID)
    10008931743
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4473868
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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