Syntheses and properties of new photochromic diarylethene derivatives having a pyrazole unit

被引:111
作者
Pu, Shouzhi [1 ]
Yang, Tianshe [1 ]
Xu, Jingkun [1 ]
Chen, Bing [1 ]
机构
[1] Jiangxi Sci & Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetlet.2006.06.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New photochromic diarylethenes 1a, 2a and 3a bearing a pyrazole unit have been synthesized. Their properties, including photochromic reactivity, fluorescence and electrochemical properties were investigated, These compounds showed good photochromic properties, high cycloreversion quantum yield and relatively strong fluorescence. The cycloreversion quantum yields of 1a, 2a and 3a are 0.46, 0.53 and 0.57, respectively, which are larger than those of their cyclization quantum yields (0.43, 0.45 and 0.47, respectively). The oxidations of diarylethenes 1a, 2a and 3a were initiated at 0.73, 1.11 and 0.79 V, respectively. Moreover, the position of the methoxyl substituent had remarkable impacts on the above optical and electrochemical properties. (c) 2006 Published by Elsevier Ltd.
引用
收藏
页码:6473 / 6477
页数:5
相关论文
共 37 条
[1]  
Brown G. H., 1971, Photochromism
[2]   Reversible near-infrared fluorescence switch by novel photochromic unsymmetrical-phthalocyanine hybrids based on bisthienylethene [J].
Chen, BZ ;
Wang, MZ ;
Wu, YQ ;
Tian, H .
CHEMICAL COMMUNICATIONS, 2002, (10) :1060-1061
[3]   Study on photochromism of diarylethenes with a 2,5-dihydropyrrole bridging unit: A convenient preparation of 3,4-diarylpyrroles from 3,4-diaryl-2,5-dihydropyrroles [J].
Chen, Y ;
Zeng, DX ;
Xie, N ;
Dang, YZ .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5001-5005
[4]   Selective photoswitching of a dyad with diarylethene and spiropyran units [J].
Choi, H ;
Ku, BS ;
Keum, SR ;
Kang, SO ;
Ko, J .
TETRAHEDRON, 2005, 61 (15) :3719-3723
[5]  
Durr H., 1990, PHOTOCHROMISM MOL SY
[6]   Reaction dynamics of photochromic dithienylethene derivatives [J].
Ern, J ;
Bens, AT ;
Martin, HD ;
Mukamel, S ;
Schmid, D ;
Tretiak, S ;
Tsiper, E ;
Kryschi, C .
CHEMICAL PHYSICS, 1999, 246 (1-3) :115-125
[7]  
Fan MG, 1999, T APPL CHEM, V1, P141
[8]   Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level [J].
Fukaminato, T ;
Sasaki, T ;
Kawai, T ;
Tamai, N ;
Irie, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) :14843-14849
[9]   Fluorescence of photochromic 1,2-bis(3-methyl-2-thienyl)ethene [J].
Fukaminato, T ;
Kawai, T ;
Kobatake, S ;
Irie, M .
JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (33) :8372-8377
[10]   Synthesis and properties of novel fluorescent switches [J].
Golovkova, TA ;
Kozlov, DV ;
Neckers, DC .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5545-5549