Control over molecular motion using the cis-trans photoisomerization of the azo group

被引:415
作者
Merino, Estibaliz [1 ]
Ribagorda, Maria [2 ]
机构
[1] CSIC, Inst Quim Organ Gen, Madrid 28006, Spain
[2] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 8卷
关键词
azobenzenes; molecular switches; nanomachines; photoisomerization; IONOTROPIC GLUTAMATE RECEPTORS; DNA-BINDING SPECIFICITY; AZOBENZENE PHOTOSWITCHES; PHOTOCHEMICAL REGULATION; TEMPERATURE DEPENDENCE; CONFORMATIONAL SWITCH; PHOTOCHROMIC AGONIST; CONTAINING POLYMERS; CYCLIC POLYETHERS; E ISOMERIZATION;
D O I
10.3762/bjoc.8.119
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Control over molecular motion represents an important objective in modern chemistry. Aromatic azobenzenes are excellent candidates as molecular switches since they can exist in two forms, namely the cis (Z) and trans (E) isomers, which can interconvert both photochemically and thermally. This transformation induces a molecular movement and a significant geometric change, therefore the azobenzene unit is an excellent candidate to build dynamic molecular devices. We describe selected examples of systems containing an azobenzene moiety and their motions and geometrical changes caused by external stimuli.
引用
收藏
页码:1071 / 1090
页数:20
相关论文
共 141 条
[11]   Artificial molecular motors and machines: Design principles and prototype systems [J].
Balzani, V ;
Credi, A ;
Ferrer, B ;
Silvi, S ;
Venturi, M .
MOLECULAR MACHINES, 2005, 262 :1-27
[12]  
Balzani V.S. F., 1991, Supramolecular Photochemistry
[13]   Photoisomerization in different classes of azobenzene [J].
Bandara, H. M. Dhammika ;
Burdette, Shawn C. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (05) :1809-1825
[14]   Light-activated ion channels for remote control of neuronal firing [J].
Banghart, M ;
Borges, K ;
Isacoff, E ;
Trauner, D ;
Kramer, RH .
NATURE NEUROSCIENCE, 2004, 7 (12) :1381-1386
[15]   Azobenzene Photoswitching without Ultraviolet Light [J].
Beharry, Andrew A. ;
Sadovski, Oleg ;
Woolley, G. Andrew .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19684-19687
[16]   Azobenzene photoswitches for biomolecules [J].
Beharry, Andrew A. ;
Woolley, G. Andrew .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (08) :4422-4437
[17]   Fluorescence Imaging of Azobenzene Photoswitching In Vivo [J].
Beharry, Andrew A. ;
Wong, Loksum ;
Tropepe, Vince ;
Woolley, G. Andrew .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) :1325-1327
[18]   CIS-TRANS PHOTOISOMERIZATION OF AZOBENZENE - SOLVENT AND TRIPLET DONOR EFFECTS [J].
BORTOLUS, P ;
MONTI, S .
JOURNAL OF PHYSICAL CHEMISTRY, 1979, 83 (06) :648-652
[19]   α-Helix formation in a photoswitchable peptide tracked from picoseconds to microseconds by time-resolved IR spectroscopy [J].
Bredenbeck, J ;
Helbing, J ;
Kumita, JR ;
Woolley, GA ;
Hamm, P .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (07) :2379-2384
[20]   CIS-TRANS ISOMERISM IN PYRIDYL ANALOGS OF AZOBENZENE - KINETIC AND MOLECULAR-ORBITAL ANALYSIS [J].
BROWN, EV ;
GRANNEMAN, GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :621-627