Dynamic Combinatorial Donor-Acceptor Catenanes in Water: Access to Unconventional and Unexpected Structures

被引：38
作者：
Au-Yeung, Ho Yu [1 ]
Pantos, G. Dan [1 ]
Sanders, Jeremy K. M. [1 ]
机构：
[1] Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 05期
基金：
英国工程与自然科学研究理事会;
关键词：
TEMPLATED SYNTHESIS; CATENATION; CHEMISTRY; PD; PSEUDOROTAXANES; AMPLIFICATION; INTERLOCKING; MACROCYCLES; DERIVATIVES; COMPLEXES;
D O I：
10.1021/jo101981p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe here the assembly of new types of donor-acceptor [2]catenanes from dynamic combinatorial libraries (DCL) in water. These new catenanes contain both the donor and acceptor components in at least one of the interlocked rings, thereby possessing unusual and unexpected DAAD or DADD stacking sequences of the it units in their structures. The efficiency of the catenane assembly process can be enhanced by manipulating the DCL equilibrium in a variety of ways: adding a guest. changing the building block stoichiometries, or increasing the library concentration or the ionic strength of the solvent. The formation of catenanes and their constitutions are found to be dependent on subtle differences in the geometry, dimension, and flexibility of the donor building blocks.
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收藏
页码：1257 / 1268
页数：12
相关论文
共 114 条
[1]   Nondegenerate π-donor/π-acceptor [2]catenanes containing proton-ionizable 1H-1,2,4-triazole subunits:: Synthesis and spontaneous resolution [J].
Alcalde, Ermitas ;
Perez-Garcia, Lluisa ;
Ramos, Susana ;
Stoddart, J. Fraser ;
White, Andrew J. P. ;
Williams, David L. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (14) :3964-3979
[2]   pH-responsive supramolecular nanovalves based on cucurbit[6]uril pseudorotaxanes [J].
Angelos, Sarah ;
Yang, Ying-Wei ;
Patel, Kaushik ;
Stoddart, J. Fraser ;
Zink, Jeffrey I. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2222-2226
[3]   Dual-Controlled Nanoparticles Exhibiting AND Logic [J].
Angelos, Sarah ;
Yang, Ying-Wei ;
Khashab, Niveen M. ;
Stoddart, J. Fraser ;
Zink, Jeffrey I. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (32) :11344-+
[4]   THE SELF-ASSEMBLY OF CATENATED CYCLODEXTRINS [J].
ARMSPACH, D ;
ASHTON, P ;
MOORE, CP ;
SPENCER, N ;
STODDART, JF ;
WEAR, TJ ;
WILLIAMS, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (06) :854-858
[5]   CATENATED CYCLODEXTRINS [J].
ARMSPACH, D ;
ASHTON, PR ;
BALLARDINI, R ;
BALZANI, V ;
GODI, A ;
MOORE, CP ;
PRODI, L ;
SPENCER, N ;
STODDART, JF ;
TOLLEY, MS ;
WEAR, TJ ;
WILLIAMS, DJ .
CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (01) :33-55
[6]   Recognition of bipyridinium-based derivatives by hydroquinone- and/or dioxynaphthalene-based macrocyclic polyethers: From inclusion complexes to the self-assembly of [2]catenanes [J].
Asakawa, M ;
Ashton, PR ;
Boyd, SE ;
Brown, CL ;
Gillard, RE ;
Kocian, O ;
Raymo, FM ;
Stoddart, JF ;
Tolley, MS ;
White, AJP ;
Williams, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :26-37
[7]   Exploiting donor-acceptor interactions in aqueous dynamic combinatorial libraries: exploratory studies of simple systems [J].
Au-Yeung, Ho Yu ;
Cougnon, Fabien B. L. ;
Otto, Sijbren ;
Pantos, G. Dan ;
Sanders, Jeremy K. M. .
CHEMICAL SCIENCE, 2010, 1 (05) :567-574
[8]   A Water Soluble Donor-Acceptor [2]Catenane that Can Switch between a Coplanar and a Gemini-Sign Conformation [J].
Au-Yeung, Ho Yu ;
Pantos, G. Dan ;
Sanders, Jeremy K. M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5331-5334
[9]   Amplifying Different [2]Catenanes in an Aqueous Donor-Acceptor Dynamic Combinatorial Library [J].
Au-Yeung, Ho Yu ;
Pantos, G. Dan ;
Sanders, Jeremy K. M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (44) :16030-+
[10]   Templated amplification of a naphthalenediimide-based receptor from a donor-acceptor dynamic combinatorial library in water [J].
Au-Yeung, Ho Yu ;
Pengo, Paolo ;
Pantos, G. Dan ;
Otto, Sijbren ;
Sanders, Jeremy K. M. .
CHEMICAL COMMUNICATIONS, 2009, (04) :419-421
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