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
  • [21] [2]Rotaxanes through palladium active-template oxidative Heck cross-couplings
    Crowley, James D.
    Hanni, Kevin D.
    Lee, Ai-Lan
    Leigh, David A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) : 12092 - +
  • [22] Diels-Alder Active-Template Synthesis of Rotaxanes and Metal-Ion-Switchable Molecular Shuttles
    Crowley, James D.
    Haenni, Kevin D.
    Leigh, David A.
    Slawin, Alexandra M. Z.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) : 5309 - 5314
  • [23] Active metal template synthesis of rotaxanes, catenanes and molecular shuttles
    Crowley, James D.
    Goldup, Stephen M.
    Lee, Ai-Lan
    Leigh, David A.
    McBurney, Roy T.
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (06) : 1530 - 1541
  • [24] Molecular knots
    Dietrich-Buchecker, C
    Colasson, BX
    Sauvage, JP
    [J]. TEMPLATES IN CHEMISTRY II, 2005, 249 : 261 - 283
  • [25] STRUCTURE OF A SYNTHETIC TREFOIL KNOT COORDINATED TO 2 COPPER(I) CENTERS
    DIETRICHBUCHECKER, CO
    GUILHEM, J
    PASCARD, C
    SAUVAGE, JP
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (10): : 1154 - 1156
  • [26] A SYNTHETIC MOLECULAR TREFOIL KNOT
    DIETRICHBUCHECKER, CO
    SAUVAGE, JP
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (02): : 189 - 192
  • [27] SYNTHESIS OF A DNA KNOT CONTAINING BOTH POSITIVE AND NEGATIVE NODES
    DU, SM
    SEEMAN, NC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) : 9652 - 9655
  • [28] THE CONSTRUCTION OF A TREFOIL KNOT FROM A DNA BRANCHED JUNCTION MOTIF
    DU, SM
    SEEMAN, NC
    [J]. BIOPOLYMERS, 1994, 34 (01) : 31 - 37
  • [29] Design and synthesis of porphyrin-containing catenanes and rotaxanes
    Faiz, Jonathan A.
    Heitz, Valerie
    Sauvage, Jean-Pierre
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (02) : 422 - 442
  • [30] Feigel M., 2006, ANGEW CHEM, V118, P5827