Photoswitch based on remarkably simple naphthopyrans

被引:36
作者
Sallenave, X
Delbaere, S
Vermeersch, G
Saleh, A
Pozzo, JL
机构
[1] CNRS, UMR 5802, F-33405 Talence, France
[2] Univ Lille 2, Fac Pharm, CNRS, UMR 8009, F-59006 Lille, France
[3] Assiut Univ, Fac Sci, Dept Chem, Assiut 71516, Egypt
关键词
photoswitch; naphthopyrans; F-19; NMR; photochromism;
D O I
10.1016/j.tetlet.2005.02.091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photochromic switches built around 5-carbonyl-3,3-diphenyl-3H-naphtho[2,1-b]pyran unit have been synthesized. Their open forms are constituted of a 1:1 ratio of TC and TT-isomers according to F-19 and H-1 NMR investigations. Electrocyclization of TT isomers back to the closed form is efficiently achieved upon visible irradiation whereas it has been found to be a particularly unfavoured thermal process. These simple 2H-chromenes could act as molecular photoswitch at ambient temperature. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3257 / 3259
页数:3
相关论文
共 18 条
[1]   Multiaddressable self-assembling organogelators based on 2H-chromene and N-acyl-1,ω-amino acid units [J].
Ahmed, SA ;
Sallenave, X ;
Fages, F ;
Mieden-Gundert, G ;
Müller, WM ;
Müller, U ;
Vögtle, F ;
Pozzo, JL .
LANGMUIR, 2002, 18 (19) :7096-7101
[2]   Organic photochromism [J].
Bouas-Laurent, H ;
Dürr, H .
PURE AND APPLIED CHEMISTRY, 2001, 73 (04) :639-665
[3]  
Crano JC, 1999, T APPL CHEM, P1
[4]   NMR kinetic investigations of the photochemical and thermal reactions of a photochromic chromene [J].
Delbaere, S ;
Micheau, JC ;
Vermeersch, G .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :8968-8973
[5]   NMR proofs of the involvement of an allenyl-naphthol as a key-intermediate in the photochromic process of [3H]-naphthopyrans [J].
Delbaere, S ;
Vermeersch, G .
TETRAHEDRON LETTERS, 2003, 44 (02) :259-262
[6]  
Feringa B.L., 2001, Molecular Switches
[7]   Room temperature nematic photoswitchable liquid crystals - Molecular modularisation of functional elements [J].
Frigoli, M ;
Mehl, GH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (03) :636-642
[8]  
HOBLEY J, 2003, MOL SUPRAMOL PHOTOCH, P355
[9]   Diarylethenes for memories and switches [J].
Irie, M .
CHEMICAL REVIEWS, 2000, 100 (05) :1685-1716
[10]   Organic chemistry: A digital fluorescent molecular photoswitch [J].
Irie, M ;
Fukaminato, T ;
Sasaki, T ;
Tamai, N ;
Kawai, T .
NATURE, 2002, 420 (6917) :759-760