Synthesis of a polypseudorotaxane, polyrotaxane, and polycatenane using 'click' chemistry

被引：29

作者：

Bria, Marc ^{[2
]}

Bigot, Julien ^{[3
]}

Cooke, Graeme ^{[1
]}

Lyskawa, Joel ^{[3
]}

Rabani, Gouher ^{[1
]}

Rotello, Vincent M. ^{[4
]}

Woisel, Patrice ^{[3
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow Ctr Phys Organ Chem, Glasgow G12 8QQ, Lanark, Scotland

[2] Univ Lille 1, CCM RMN Lille 1, F-59655 Villeneuve Dascq, France

[3] Univ Lille 1, Lab Chim Organ & Macromol, UMR Chim Organ & Macromol 8009, F-59655 Villeneuve Dascq, France

[4] Univ Massachusetts, Dept Chem, Amherst, MA 01003 USA

来源：

TETRAHEDRON | 2009年 / 65卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

Interlocked molecules; Polymers; Click chemistry; Cyclobis(paraquat-p-phenylene); CATALYZED AZIDE-ALKYNE; 1,3-DIPOLAR CYCLOADDITIONS; MOLECULAR MECCANO; SOLID-PHASE; ROTAXANES; POLYMERS; COMBINATION; LIGATION; BEHAVIOR; DONOR;

D O I：

10.1016/j.tet.2008.10.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a polypseudorotaxane, polyrotaxane, and polycatenane containing the electron-deficient cyclophane cyclobis(paraquat-p-phenylene) (CBPQT(4+)) subunit in the side chain is described. These interlocked supramolecular polymers have been prepared from an azide-functionalized polystyrene derivative and an acetylene-functionalized [2]rotaxane, [2]catenane and their parent tetracationic cyclophane via Cu(I)-catalyzed 1,3 dipolar cycloadditions ('click chemistry'). The synthesis and characterization of the polymers and intermediates has been described using IR, H-1 NMR, UV spectroscopies, and voltammetry. We have shown that the CBPQT(4+) unit of the side chain polystyrene derivative has the ability to reversibly undergo complexation with a complementary dialkoxynaphthatene derivative. (C) 2008 Published by Elsevier Ltd.

引用

页码：400 / 407

页数：8

共 53 条

[41] Interlocked macromolecules [J].

Raymo, FM ;

Stoddart, JF .

CHEMICAL REVIEWS, 1999, 99 (07) :1643-1663

[42]

Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO

[43]

2-4

[44] New photolabile functional polymers for patterning onto gold obtained by click chemistry [J].

Sieczkowska, Barbara ;

Millaruelo, Marta ;

Messerschmidt, Martin ;

Voit, Brigitte .

MACROMOLECULES, 2007, 40 (07) :2361-2370

[45] A one-pot synthesis of constitutionally unsymmetrical rotaxanes using sequential CuI-catalyzed azide-alkyne cycloadditions [J].

Spruell, Jason M. ;

Dichtel, William R. ;

Heath, James R. ;

Stoddart, J. Fraser .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (14) :4168-4177

[46] Polyrotaxanes and polycatenanes: Recent advances in syntheses and applications of polymers comprising of interlocked structures [J].

Takata, T ;

Kihara, N ;

Furusho, Y .

POLYMER SYNTHESIS, 2004, 171 :1-75

[47] Polyrotaxane and polyrotaxane network: Supramolecular architectures based on the concept of dynamic covalent bond chemistry [J].

Takata, T .

POLYMER JOURNAL, 2006, 38 (01) :1-20

[48] Polyrotaxane/DNA conjugate by use of intercalation: Bridge formation between DNA double helices [J].

Tokuhisa, Kenji ;

Hamada, Emi ;

Karinaga, Ryouji ;

Shimada, Naohiko ;

Takeda, Yoichi ;

Kawasaki, Shinichi ;

Sakurai, Kazuo .

MACROMOLECULES, 2006, 39 (26) :9480-9485

[49] Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides [J].

Tornoe, CW ;

Christensen, C ;

Meldal, M .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3057-3064

[50] Catalytic self-threading: A new route for the synthesis of polyrotaxanes [J].

Tuncel, D ;

Steinke, JHG .

MACROMOLECULES, 2004, 37 (02) :288-302

← 1 2 3 4 5 6 →