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

作者: Benedict Sandmann , Bobby Happ , Jürgen Vitz , Renzo M. Paulus , Martin D. Hager

DOI: 10.1002/MACP.201400149

关键词:

摘要: The synthesis of three different electron-defi cient internal alkynes for the metal-free 1,3-dipolar azide–alkyne cycloaddition is shown. are polymerized with several multifunctional azides and reaction enthalpy (Δ H ) investigated by differential scanning calorimetry (DSC). mechanical properties resulting polymers analyzed using nanoindentation. polymerization results in hard materials an E -modulus maximum 2.5 GPa, which make them interesting particular biomedical applications.

参考文章(29)
Yujing Li, Hao Zhou, Yanpeng E, Liqiang Wan, Farong Huang, Lei Du, Synthesis and characterization of a new series of rigid polytriazole resins Designed Monomers and Polymers. ,vol. 16, pp. 556- 563 ,(2013) , 10.1080/15685551.2013.771308
Christian W. Tornøe, Caspar Christensen, Morten Meldal, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry. ,vol. 67, pp. 3057- 3064 ,(2002) , 10.1021/JO011148J
Liqiang Wan, Jianjun Tian, Jianzhi Huang, Yanhong Hu, Farong Huang, Lei Du, Synthesis and Characterization of a Novel Polytriazole Journal of Macromolecular Science, Part A. ,vol. 44, pp. 175- 181 ,(2007) , 10.1080/10601320601031341
Erik F.-J. Rettler, Johannes M. Kranenburg, Hanneke M.L. Lambermont-Thijs, Richard Hoogenboom, Ulrich S. Schubert, Thermal, Mechanical, and Surface Properties of Poly(2-N-alkyl-2-oxazoline)s Macromolecular Chemistry and Physics. ,vol. 211, pp. 2443- 2448 ,(2010) , 10.1002/MACP.201000338
HongKun Li, Ju Mei, Jian Wang, Shuang Zhang, QiuLi Zhao, Qiang Wei, AnJun Qin, JingZhi Sun, Ben Zhong Tang, Facile synthesis of poly(aroxycarbonyltriazole)s with aggregation-induced emission characteristics by metal-free click polymerization Science China Chemistry. ,vol. 54, pp. 611- 616 ,(2011) , 10.1007/S11426-011-4235-9
Alan R Katritzky, Rajeev Sakhuja, Longchuan Huang, Reena Gyanda, Ling Wang, David Carnaby Jackson, David A Ciaramitaro, Clifford D Bedford, Randolph S Duran, None, Effect of filler loading on the mechanical properties of crosslinked 1,2,3‐triazole polymers Journal of Applied Polymer Science. ,vol. 118, pp. 121- 127 ,(2010) , 10.1002/APP.32257
Anjun Qin, Li Tang, Jacky W. Y. Lam, Cathy K. W. Jim, Yong Yu, Hui Zhao, Jingzhi Sun, Ben Zhong Tang, Metal‐Free Click Polymerization: Synthesis and Photonic Properties of Poly(aroyltriazole)s Advanced Functional Materials. ,vol. 19, pp. 1891- 1900 ,(2009) , 10.1002/ADFM.200801933
Alan R. Katritzky, Nabin K. Meher, Sureyya Hanci, Reena Gyanda, Srinivasa R. Tala, Sindhu Mathai, Randolph S. Duran, Sophie Bernard, Firouzeh Sabri, Sandeep K. Singh, Jacek Doskocz, David A. Ciaramitaro, Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes Journal of Polymer Science Part A. ,vol. 46, pp. 238- 256 ,(2008) , 10.1002/POLA.22376
Ling Wang, Yuming Song, Reena Gyanda, Rajeev Sakhuja, Nabin K. Meher, Sureyya Hanci, Kapil Gyanda, Sindhu Mathai, Firouzeh Sabri, David A. Ciaramitaro, Clifford D. Bedford, Alan R. Katritzky, Randolph S. Duran, Preparation and mechanical properties of crosslinked 1,2,3‐triazole‐polymers as potential propellant binders Journal of Applied Polymer Science. ,vol. 117, pp. 2612- 2621 ,(2010) , 10.1002/APP.30753
Jianjun Tian, Liqiang Wan, Jianzhi Huang, Yanhong Hu, Farong Huang, Lei Du, Preparation and properties of a new polytriazole resin made from dialkyne and triazide compounds and its composite Polymer Bulletin. ,vol. 60, pp. 457- 465 ,(2008) , 10.1007/S00289-007-0878-2