Molecular switches flipped by oxygen

被引:72
作者
Zehm, Daniel [1 ]
Fudickar, Werner [1 ]
Linker, Torsten [1 ]
机构
[1] Univ Potsdam, Dept Chem, Karl Liebknecht Str 24-25, D-14476 Potsdam, Germany
关键词
acenes; axial rotation; molecular switches; oxidation; peroxides;
D O I
10.1002/anie.200700443
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Singlet oxygen fuels anthracenes and forces an axial rotation of aryl substituents during the oxidation. The molecular switch can be synthesized in only one step from commercially available starting materials. Thermal cleavage of the resulting endoperoxides proceeds quantitatively and affords a simple 180° switch with oxygen as the only waste product. The initial trans state is attained by heating, and repetitive cycles are possible. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7689 / 7692
页数:4
相关论文
共 58 条
[1]   pi-Facial diastereoselectivity in the [4+2] cycloaddition of singlet oxygen as a mechanistic probe [J].
Adam, W ;
Prein, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :275-283
[2]  
[Anonymous], 2001, ACC CHEM RES, V34
[3]  
[Anonymous], 2002, Molecular Motors
[4]   Reversible binding of oxygen to aromatic compounds [J].
Aubry, JM ;
Pierlot, C ;
Rigaudy, J ;
Schmidt, R .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (09) :668-675
[5]  
BALLARDINI R, 2001, ACCOUNTS CHEM RES, V34, P224
[6]  
Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO
[7]  
2-X
[8]  
Balzani V., 2003, Molecular Devices and Machines, a Journey into the Nanoworld
[9]   A CHEMICALLY AND ELECTROCHEMICALLY SWITCHABLE MOLECULAR SHUTTLE [J].
BISSELL, RA ;
CORDOVA, E ;
KAIFER, AE ;
STODDART, JF .
NATURE, 1994, 369 (6476) :133-137
[10]   Photoinduction of fast, reversible translational motion in a hydrogen-bonded molecular shuttle [J].
Brouwer, AM ;
Frochot, C ;
Gatti, FG ;
Leigh, DA ;
Mottier, L ;
Paolucci, F ;
Roffia, S ;
Wurpel, GWH .
SCIENCE, 2001, 291 (5511) :2124-2128