Dynamic combinatorial synthesis of a catenane based on donor-acceptor interactions in water

被引：117

作者：

Au-Yeung, Ho Yu ^{[1
]}

Pantos, G. Dan ^{[1
]}

Sanders, Jeremy K. M. ^{[1
]}

机构：

[1] Univ Cambridge, Univ Chem Lab, Lensfield Rd, Cambridge CB2 1EW, England

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2009年 / 106卷 / 26期

基金：

英国工程与自然科学研究理事会;

关键词：

dynamic combinatorial chemistry; molecular recognition; AMPLIFICATION; LIBRARIES; RECEPTOR;

D O I：

10.1073/pnas.0809934106

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

A new type of neutral donor-acceptor [2]-catenane, containing both complementary units in the same ring was synthesized from a dynamic combinatorial library in water. The yield of the water soluble [2]-catenane is enhanced by increasing either building-block concentrations or ionic strength, or by the addition of an electron-rich template. NMR spectroscopy demonstrates that the template is intercalated between the 2 electron-deficient naphthalenediimide units of the catenane.

引用

页码：10466 / 10470

页数：5

共 37 条

[1] Clicked interlocked molecules [J].

Aprahamian, Ivan ;

Miljanic, Ognjen S. ;

Dichtel, William R. ;

Isoda, Kyosuke ;

Yasuda, Takuma ;

Kato, Takashi ;

Stoddart, J. Fraser .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2007, 80 (10) :1856-1869

[2] 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

[3] Oligothiophene-based catenanes:: Synthesis and electronic properties of a novel conjugated topological structure [J].

Baeuerle, Peter ;

Ammann, Martin ;

Wilde, Markus ;

Goetz, Guenther ;

Mena-Osteritz, Elena ;

Rang, Alexander ;

Schalley, Christoph A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (03) :363-368

[4] Molecular catenation via metal-directed self-assembly and π-donor/π-acceptor interactions:: Efficient one-pot synthesis, characterization, and crystal structures of [3]catenanes based on Pd or Pt dinuclear metallocycles [J].

Blanco, Victor ;

Chas, Marcos ;

Abella, Dolores ;

Peinador, Carlos ;

Quintela, Jose M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13978-13986

[5] Reversible formation of a [2]catenane through first- and second-sphere coordination [J].

Blight, Barry A. ;

Wisner, James A. ;

Jennings, Michael C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (16) :2835-2838

[6] Synthesis of [3]catenanes based on metal-directed self-assembly and π-donor/π-acceptor interactions [J].

Chas, Marcos ;

Blanco, Victor ;

Peinador, Carlos ;

Quintela, Jose M. .

ORGANIC LETTERS, 2007, 9 (04) :675-678

[7] Dynamic combinatorial chemistry [J].

Corbett, Peter T. ;

Leclaire, Julien ;

Vial, Laurent ;

West, Kevin R. ;

Wietor, Jean-Luc ;

Sanders, Jeremy K. M. ;

Otto, Sijbren .

CHEMICAL REVIEWS, 2006, 106 (09) :3652-3711

[8] A reverse donor-acceptor bistable [2]Catenane [J].

Coskun, Ali ;

Saha, Sourav ;

Aprahamian, Ivan ;

Stoddart, J. Fraser .

ORGANIC LETTERS, 2008, 10 (15) :3187-3190

[9]

Cousins GRL, 2001, ANGEW CHEM INT EDIT, V40, P423, DOI 10.1002/1521-3773(20010119)40:2<423::AID-ANIE423>3.0.CO

[10]

2-6

← 1 2 3 4 →