Synthesis and photochromic reactivity of a diarylethene dimer linked by a phenyl group

被引:88
作者
Kobatake, S [1 ]
Irie, M [1 ]
机构
[1] Kyushu Univ, Grad Sch Engn, Dept Chem & Biochem, Higashi Ku, Fukuoka 8128581, Japan
关键词
diarylethene; photochromism; quantum yield; dimer; color change;
D O I
10.1016/j.tet.2003.08.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A diarylethene dimer linked by a phenyl group was synthesized and the photochromic behavior was examined. Upon irradiation with ultraviolet light (lambda=313 nm), a hexane solution of the diarylethene dimer (1a) turned purple blue. Upon further prolonged irradiation the color changed to blue. The purple-blue and blue colors are due to the formation of a dimer having one open- and one closed-ring forms (1b) and a dimer having two closed-ring forms (1c), respectively. Both 1b and 1c returned to la by irradiation with visible light (lambda>500 nm). The photochromic reactivity was evaluated by measuring quantum yields of the photocyclization and photocycloreversion reactions. The photocyclization quantum yield was 0.50. The cycloreversion quantum yield from 1c to 1b (0.0026) was lower than that from 1b to 1a (0.0094). (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8359 / 8364
页数:6
相关论文
共 43 条
  • [1] Bens AT, 1998, EUR J ORG CHEM, V1998, P2333
  • [2] Brown G. H., 1971, Photochromism
  • [3] SYNTHESIS OF NEW PHOTOCHROMIC POLYMERS BASED ON PHENOXYNAPHTHACENEQUINONE
    BUCHHOLTZ, F
    ZELICHENOK, A
    KRONGAUZ, V
    [J]. MACROMOLECULES, 1993, 26 (05) : 906 - 910
  • [4] Highly fluorescent and photochromic diarylethene oligomer bridged by p-phenylenevinylene
    Cho, H
    Kim, E
    [J]. MACROMOLECULES, 2002, 35 (23) : 8684 - 8687
  • [5] PHOTOCHROMIC HETEROCYCLIC FULGIDES .2. ELECTROCYCLIC REACTIONS OF (E)-ALPHA-2,5-DIMETHYL-3-FURYLETHYLIDENE(ALKYL-SUBSTITUTED METHYLENE)-SUCCINIC ANHYDRIDES
    DARCY, PJ
    HELLER, HG
    STRYDOM, PJ
    WHITTALL, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01): : 202 - 205
  • [6] Durr H., 1990, PHOTOCHROMISM MOL SY
  • [7] SYNTHESIS AND PHOTOCHROMISM IN SOLUTION OF PHENOXYNAPHTHACENEQUINONE DERIVATIVES
    FANG, Z
    WANG, SZ
    YANG, ZF
    CHEN, B
    LI, FT
    WANG, JQ
    XU, SX
    JIANG, ZJ
    FANG, TR
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1995, 88 (01) : 23 - 30
  • [8] Three-dimensional erasable optical memory using a photochromic diarylethene single crystal as the recording medium
    Fukaminato, T
    Kobatake, S
    Kawai, T
    Irie, M
    [J]. PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2001, 77 (02): : 30 - 35
  • [9] HELLER HG, 1991, J CHEM SOC P1, P197
  • [10] Reversible surface morphology changes of a photochromic diarylethene single crystal by photoirradiation
    Irie, M
    Kobatake, S
    Horichi, M
    [J]. SCIENCE, 2001, 291 (5509) : 1769 - 1772