A new model of light-powered chiral molecular motor with higher speed of rotation, part 2 - Dynamics of motor rotation

被引:21
作者
Kuwahara, S [1 ]
Fujita, T [1 ]
Harada, N [1 ]
机构
[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, Sendai, Miyagi 9808577, Japan
关键词
molecular motor; motor rotation isomer; circular dichroism; molecular dynamics;
D O I
10.1002/ejoc.200500323
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
To clarify the mechanism and dynamics of the new model of light-powered chiral molecular motor (2) of five-membered ring type, the second motor rotation isomer, the unstable cis-olefin 2b, was isolated and its stereostructure was determined. Similarly, the fourth motor rotation isomer, the unstable trans-olefin 2d, was detected by H-1 NMR at low temperature, and its stereostructure was also determined. With the aid of this knowledge of the stereo structures of the motor rotation isomers and their spectroscopic data, the dynamics of the motor rotation 2a -> 2b 2c -> 2d -> 2a were studied by H-1 NMR and CD, revealing that the fourth rotation step 2d -> 2a was much accelerated, as expected from the design of the new motor. Continuous rotation of this motor was achieved by repetition of the operations of photoirradiation and heating. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
引用
收藏
页码:4544 / 4556
页数:13
相关论文
共 4 条
[1]  
FUJITA T, 2005, EUR J ORG CHEM
[2]   Photochemistry and absolute stereochemistry of unique chiral olefins, trans- and cis-1,1′,2,2′,3,3′,4,4′-octahydro-3,3′-dimethyl-4,4′-biphenanthrylidene [J].
Koumura, N ;
Harada, N .
CHEMISTRY LETTERS, 1998, (11) :1151-1152
[3]   AN APPARATUS FOR THE ULTRA-VIOLET SPECTROSCOPY OF SOLUTIONS AT LOW TEMPERATURES [J].
PASSERINI, R .
JOURNAL OF SCIENTIFIC INSTRUMENTS, 1953, 30 (08) :274-276
[4]   Increased speed of rotation for the smallest light-driven molecular motor [J].
ter Wiel, MKJ ;
van Delden, RA ;
Meetsma, A ;
Feringa, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (49) :15076-15086