Active-Metal Template Synthesis of a Molecular Trefoil Knot

被引:121
作者
Barran, Perdita E. [1 ]
Cole, Harriet L. [1 ]
Goldup, Stephen M. [1 ]
Leigh, David A. [1 ]
McGonigal, Paul R. [1 ]
Symes, Mark D. [1 ]
Wu, Jhenyi [1 ]
Zengerle, Michael [1 ]
机构
[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
基金
英国工程与自然科学研究理事会;
关键词
chemical topology; click chemistry; self-assembly; supramolecular chemistry; template synthesis; SINGLE-STRANDED-DNA; INTERLOCKED MOLECULES; CHEMICAL TOPOLOGY; TERMINAL ALKYNES; ROTAXANES; CATENANES; SHUTTLES; CONSTRUCTION; COPPER(I); ASSEMBLIES;
D O I
10.1002/anie.201105012
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tying the knot: The marriage of catalysis and coordination chemistry enables two Cu I ions (red; see picture) to work in partnership for the synthesis of a molecular trefoil knot. One ion entangles an acyclic building block to create a loop in the ligand, and the other gathers the ligand's reactive end-groups, threads the loop, and catalyzes the covalent capture of the knotted architecture by an alkyne-azide "click" reaction. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12280 / 12284
页数:5
相关论文
共 87 条
  • [11] Catalytic "Active-Metal" template synthesis of [2]rotaxanes, [3]rotaxanes, and molecular shuttles, and some observations on the mechanism of the Cu(I)-catalyzed azide-alkyne 1,3-cycloaddition
    Aucagne, Vincent
    Berna, Jose
    Crowley, James D.
    Goldup, Stephen M.
    Haenni, Kevin D.
    Leigh, David A.
    Lusby, Paul J.
    Ronaldson, Vicki E.
    Slawin, Alexandra M. Z.
    Viterisi, Aurlien
    Walker, D. Barney
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) : 11950 - 11963
  • [12] Berna, 2008, ANGEW CHEM, V120, P4464
  • [13] BERNA J, 2007, ANGEW CHEM, V119, P5811
  • [14] Cadiot-Chodkiewicz active template synthesis of rotaxanes and switchable molecular shuttles with weak intercomponent interactions
    Berna, Jose
    Goldup, Stephen M.
    Lee, Ai-Lan
    Leigh, David A.
    Symes, Mark D.
    Teobaldi, Gilberto
    Zerbetto, Francesco
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) : 4392 - 4396
  • [15] A catalytic palladium active-metal template pathway to [2]rotaxanes
    Berna, Jose
    Crowley, James D.
    Goldup, Stephen M.
    Haenni, Kevin D.
    Lee, Ai-Lan
    Leigh, David A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) : 5709 - 5713
  • [16] Topologically novel multiple rotaxanes and catenanes based on tetraurea calix[4]arenes
    Bogdan, Anca
    Rudzevich, Yuliya
    Vysotsky, Myroslav O.
    Boehmer, Volker
    [J]. CHEMICAL COMMUNICATIONS, 2006, (28) : 2941 - 2952
  • [17] Supramolecular topology
    Breault, GA
    Hunter, CA
    Mayers, PC
    [J]. TETRAHEDRON, 1999, 55 (17) : 5265 - 5293
  • [18] Spontaneons knotting -: From oligoamide threads to trefoil knots
    Brueggemann, Jens
    Bitter, Stephan
    Mueller, Sonja
    Mueller, Walter M.
    Mueller, Ute
    Maier, Norbert M.
    Lindner, Wolfgang
    Voegtle, Fritz
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) : 254 - 259
  • [19] Bruggemann J., 2007, ANGEW CHEM, V119, P258
  • [20] En Route to a Molecular Sheaf: Active Metal Template Synthesis of a [3]Rotaxane with Two Axles Threaded through One Ring
    Cheng, Hei Man
    Leigh, David A.
    Maffei, Francesca
    McGonigal, Paul R.
    Slawin, Alexandra M. Z.
    Wu, Jhenyi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) : 12298 - 12303