A reverse donor-acceptor bistable [2]Catenane

被引:48
作者
Coskun, Ali [1 ,2 ,3 ]
Saha, Sourav [1 ,2 ]
Aprahamian, Ivan [1 ,2 ]
Stoddart, J. Fraser [1 ,2 ,3 ]
机构
[1] Univ Calif Los Angeles, Calif NanoSyst Inst, Los Angeles, CA 90095 USA
[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[3] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
D O I
10.1021/ol800931z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A [2]catenane, composed of a pi-electron-rich bis-1,5-dioxynaphthalene[38]crown10 (BDNP38C10) ring, mechanically interlocked with a large macrocycle containing two disubstituted tetraarylmethane "speed bumps" and two different pi-electron-deficient units-namely, naphthalene dimide (Npl) and bipyridinium (Blpy(2+)) units-has been synthesized from a [2]rotaxane, containing the former recognition unit, after performing two sequential Cu(l)-catalyzed azide-alkyne cycloadditions with a linker containing the latter recognition unit. The product, which exists as a single co-conformer, wherein the BDNP38C10 ring encircles the Npl unit, undergoes equilibration to give approximately equal amounts of the other co-conformer in which the BDNP38C10 ring encircles the Blpy(2+) unit.
引用
收藏
页码:3187 / 3190
页数:4
相关论文
共 53 条
[1]   EXPANDING ROLES FOR TEMPLATES IN SYNTHESIS [J].
ANDERSON, S ;
ANDERSON, HL ;
SANDERS, JKM .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (09) :469-475
[2]   A liquid-crystalline bistable [2]Rotaxane [J].
Aprahamian, Ivan ;
Yasuda, Takuma ;
Ikeda, Taichi ;
Saha, Sourav ;
Dichtel, William R. ;
Isoda, Kyosuke ;
Kato, Takashi ;
Stoddart, J. Fraser .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4675-4679
[3]  
Asakawa M, 1998, ANGEW CHEM INT EDIT, V37, P333, DOI 10.1002/(SICI)1521-3773(19980216)37:3<333::AID-ANIE333>3.0.CO
[4]  
2-P
[5]   THE SELF-ASSEMBLY OF [2]-ROTAXANES AND [3]-ROTAXANES BY SLIPPAGE [J].
ASHTON, PR ;
BELOHRADSKY, M ;
PHILP, D ;
SPENCER, N ;
STODDART, JF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (16) :1274-1277
[6]   Autonomous artificial nanomotor powered by sunlight [J].
Balzani, V ;
Clemente-León, M ;
Credi, A ;
Ferrer, B ;
Venturi, M ;
Flood, AH ;
Stoddart, JF .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (05) :1178-1183
[7]   Macroscopic transport by synthetic molecular machines [J].
Berná, J ;
Leigh, DA ;
Lubomska, M ;
Mendoza, SM ;
Pérez, EM ;
Rudolf, P ;
Teobaldi, G ;
Zerbetto, F .
NATURE MATERIALS, 2005, 4 (09) :704-710
[8]   A CHEMICALLY AND ELECTROCHEMICALLY SWITCHABLE MOLECULAR SHUTTLE [J].
BISSELL, RA ;
CORDOVA, E ;
KAIFER, AE ;
STODDART, JF .
NATURE, 1994, 369 (6476) :133-137
[9]  
Blanco MJ, 2003, TOP STEREOCHEM, V23, P125
[10]   Supramolecular topology [J].
Breault, GA ;
Hunter, CA ;
Mayers, PC .
TETRAHEDRON, 1999, 55 (17) :5265-5293