Metal-Free Cycloaddition of Internal Alkynes and Multifunctional Azides Under Solvent-Free Conditions

被引：30
作者：
Sandmann, Benedict [1 ,2 ]
Happ, Bobby [1 ,2 ,3 ]
Vitz, Juergen [1 ,2 ,3 ]
Paulus, Renzo M. [1 ,2 ]
Hager, Martin D. [1 ,2 ]
Burtscher, Peter [4 ]
Moszner, Norbert [4 ]
Schubert, U. S. [1 ,2 ,3 ]
机构：
[1] Univ Jena, Lab Organ & Macromol Chem IOMC, D-07743 Jena, Germany
[2] Univ Jena, JCSM, D-07743 Jena, Germany
[3] DPI, NL-5600 AX Eindhoven, Netherlands
[4] Ivoclar Vivadent AG, FL-9494 Schaan, Liechtenstein
来源：
MACROMOLECULAR CHEMISTRY AND PHYSICS | 2014年 / 215卷 / 17期
关键词：
click chemistry; internal alkynes; metal-free cycloaddition; nanoindentation; FREE CLICK POLYMERIZATION; 1,3-DIPOLAR CYCLOADDITIONS; MECHANICAL-PROPERTIES; POLYTRIAZOLE RESIN; FACILE SYNTHESIS; CHEMISTRY; POLYMERS; LIGATION;
D O I：
10.1002/macp.201400149
中图分类号：
O63 [高分子化学（高聚物）];
学科分类号：
070305 ; 080501 ; 081704 ;
摘要：
The synthesis of three different electron-deficient internal alkynes for the metal-free 1,3-dipolar azide-alkyne cycloaddition is shown. The alkynes are polymerized with several multifunctional azides and the reaction enthalpy (H) is investigated by differential scanning calorimetry (DSC). The mechanical properties of the resulting polymers are analyzed using nanoindentation. The polymerization results in hard materials with an E-modulus of maximum 2.5 GPa, which make them interesting in particular for biomedical applications.
引用
收藏
页码：1603 / 1608
页数：6
相关论文
共 33 条
  • [1] Abu-Orabi ST, 1999, ASIAN J CHEM, V11, P774
  • [2] REACTION OF ACETYLENEDICARBOXALDEHYDE BIS(DIETHYL ACETAL) WITH BIS(AZIDOMETHYL)BENZENE
    ABUORABI, ST
    HARMON, RE
    [J]. JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1986, 31 (03) : 379 - 380
  • [3] New evidence for early presence of hominids in North China
    Ao, Hong
    Dekkers, Mark J.
    Wei, Qi
    Qiang, Xiaoke
    Xiao, Guoqiao
    [J]. SCIENTIFIC REPORTS, 2013, 3
  • [4] Click Chemistry beyond Metal-Catalyzed Cycloaddition
    Becer, C. Remzi
    Hoogenboom, Richard
    Schubert, Ulrich S.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (27) : 4900 - 4908
  • [5] Huisgen R., 1984, 1 3 DIPOLAR CYCLOADD, V1, P55
  • [6] Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes
    Katritzky, Alan R.
    Meher, Nabin K.
    Hanci, Sureyya
    Gyanda, Reena
    Tala, Srinivasa R.
    Mathai, Sindhu
    Duran, Randolph S.
    Bernard, Sophie
    Sabri, Firouzeh
    Singh, Sandeep K.
    Doskocz, Jacek
    Ciaramitaro, David A.
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (01) : 238 - 256
  • [7] Effect of Filler Loading on the Mechanical Properties of Cross linked 1,2,3-Triazole Polymers
    Katritzky, Alan R.
    Sakhuja, Rajeev
    Huang, Longchuan
    Gyanda, Reena
    Wang, Ling
    Jackson, David Carnaby
    Ciaramitaro, David A.
    Bedford, Clifford D.
    Duran, Randolph S.
    [J]. JOURNAL OF APPLIED POLYMER SCIENCE, 2010, 118 (01) : 121 - 127
  • [8] The growing impact of click chemistry on drug discovery
    Kolb, HC
    Sharpless, KB
    [J]. DRUG DISCOVERY TODAY, 2003, 8 (24) : 1128 - 1137
  • [9] Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO
  • [10] 2-X
1234