Helicity inversion in responsive foldamers induced by achiral halide ion guests

被引:291
作者
Meudtner, Robert M. [1 ]
Hecht, Stefan [1 ]
机构
[1] Humboldt Univ, Dept Chem, D-12489 Berlin, Germany
关键词
chirality; click chemistry; foldamers; helical polymers; helix inversion;
D O I
10.1002/anie.200800796
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Graph Presented) A surprising about-face: Click chemistry was used for the efficient synthesis of a newclass of foldamers, referred to as clickamers, that display unusual folding and recognition properties. In the presence of halide ions - achiral species - they undergo an unprecedented helix inversion. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4926 / 4930
页数:5
相关论文
共 57 条
[1]   Regulation of saccharide binding with basic poly(ethynylpyridine)s by H+-induced helix formation [J].
Abe, H ;
Masuda, N ;
Waki, M ;
Inouye, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16189-16196
[2]  
[Anonymous], ORGANIC CONFORMATION
[3]  
[Anonymous], ANGEW CHEM
[4]   Dynamic chemical devices: Modulation of contraction/extension molecular motion by coupled-ion binding/pH change-induced structural switching [J].
Barboiu, M ;
Lehn, JM .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (08) :5201-5206
[5]  
Berl V, 2000, CHEM-EUR J, V6, P1938
[6]  
Berova, 2000, CIRCULAR DICHROISM P, P337
[7]   Discrete organic nanotubes based on a combination of covalent and non-covalent approaches [J].
Block, MAB ;
Kaiser, C ;
Khan, A ;
Hecht, S .
FUNCTIONAL MOLECULAR NANOSTRUCTURES, 2005, 245 :89-150
[8]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[9]   Self-assembly of folded m-phenylene ethynylene oligomers into helical columns [J].
Brunsveld, L ;
Meijer, EW ;
Prince, RB ;
Moore, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (33) :7978-7984
[10]   Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].
Chan, TR ;
Hilgraf, R ;
Sharpless, KB ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (17) :2853-2855