Dendrimer design using CuI-catalyzed alkyne-azide "click-chemistry"

被引:162
作者
Franc, Gregory [1 ]
Kakkar, Ashok [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1039/b809870k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chemoselective [3+2] cycloaddition of an azide on to an alkyne, catalyzed by Cu-1, has become known as "click-chemistry''. The ease with which this reaction can be carried out and the formation of pure product without the need for further purification, offer a tremendous potential in developing monodisperse 1,4-disubstituted 1,2,3-triazole heterocycle based macromolecules of a diverse nature. The versatility of this approach in designing dendrimers or functionalizing them at the periphery with desired molecules has rekindled hopes in developing nanomaterials, at scales that can accelerate their entry into industrial usage.
引用
收藏
页码:5267 / 5276
页数:10
相关论文
共 90 条
  • [1] Antoni P, 2007, CHEM COMMUN, P2249, DOI 10.1039/b703547k
  • [2] Enhanced membrane pore formation by Multimeric/Oligomeric antimicrobial peptides
    Arnusch, Christopher J.
    Branderhorst, Hilbert
    De Kruijff, Ben
    Liskamp, Rob M. J.
    Breukink, Eefjan
    Pieters, Roland J.
    [J]. BIOCHEMISTRY, 2007, 46 (46) : 13437 - 13442
  • [3] Dendritic catalysts and dendrimers in catalysis
    Astruc, D
    Chardac, F
    [J]. CHEMICAL REVIEWS, 2001, 101 (09) : 2991 - 3023
  • [4] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective
    Bock, VD
    Hiemstra, H
    van Maarseveen, JH
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 51 - 68
  • [5] About dendrimers: Structure, physical properties, and applications
    Bosman, AW
    Janssen, HM
    Meijer, EW
    [J]. CHEMICAL REVIEWS, 1999, 99 (07) : 1665 - 1688
  • [6] Dendritic polymers containing a dimethylsilyl linked dihydroxybenzyl alcohol backbone: divergent synthesis, aggregation, functionalization, and an evaluation of their applications in catalysis
    Bourrier, O
    Kakkar, AK
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 2003, 13 (06) : 1306 - 1315
  • [7] Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation
    Branderhorst, Hilbert M.
    Kooij, Raymond
    Salminen, Annika
    Jongeneel, Lieneke H.
    Arnusch, Christopher J.
    Liskamp, Rob M. J.
    Finne, Jukka
    Pieters, Roland J.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (08) : 1425 - 1434
  • [8] Strong inhibition of cholera toxin binding by galactose dendrimers
    Branderhorst, Hilbert M.
    Liskamp, Rob M. J.
    Visser, Gerben M.
    Pieters, Roland J.
    [J]. CHEMICAL COMMUNICATIONS, 2007, (47) : 5043 - 5045
  • [9] First divergent strategy using two AB2 unprotected monomers for the rapid synthesis of dendrimers (vol 123, pg 6698, 2001)
    Brauge, L
    Magro, G
    Caminade, AM
    Majoral, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) : 8446 - 8446
  • [10] First divergent strategy using two AB2 unprotected monomers for the rapid synthesis of dendrimers
    Brauge, L
    Magro, G
    Caminade, AM
    Majoral, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) : 6698 - 6699