title: Polyaddition of Azide-Containing Norbornene-Based Monomer through Strain-Promoted 1,3-Dipolar Cycloaddition Reaction.
abstract: The azide-alkyne "click" reaction has been well known in the past decade, however, another kind of 1,3-dipolar cycloaddition, the azide-alkene reaction is not fully explored in polymer science to date. This contribution reports, for the first time, the discovery of a polyaddition of norbornene based monomer (NC11N3 ) containing both strained double bond and azide moieties. The reaction product is characterized by Fourier transform infrared spectroscopy (FTIR), NMR, gel permeation chromatography (GPC), and mass spectrometry (MS), which confirmed the mechanism that is through cycloaddition of azide to strained double bond on norbornene ring to form triazoline linkage. The reaction can proceed at room temperature as indicated by the increase of molecular weight and viscosity during storage. Monomer, dimer, trimer, tetramer, etc., and species with loss of N2 due to lability of triazoline moiety are identified in the mixture of reaction product. As a unique feature, elimination of N2 in the five-membered ring of triazoline affords a chance to form highly reactive materials, such as with aziridine, which can be a very powerful tool in chemical functionalizations, and find promising applications in reactive polymer resin industries.
authors.affiliation: Department of Applied Chemistry, Xi'an University of Technology, No. 5 South Jinhua Road, Xi'an, Shaanxi, 710048, P. R. China.
authors.forename: Xiaojuan
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Department of Applied Chemistry, Xi'an University of Technology, No. 5 South Jinhua Road, Xi'an, Shaanxi, 710048, P. R. China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: Department of Applied Chemistry, Xi'an University of Technology, No. 5 South Jinhua Road, Xi'an, Shaanxi, 710048, P. R. China.
authors.forename: Yuzhen
authors.initials: Y
authors.lastname: Wu
authors.affiliation: Frontier Institute of Science and Technology (FIST), Xi'an Jiaotong University, No. 99 Yanxiang Road, Xi'an, Shaanxi, 710054, P. R. China.
authors.forename: Chao
authors.initials: C
authors.lastname: Feng
authors.affiliation: Department of Oral Implantology, State Key Laboratory of Military Stomatology, School of Stomatology, The Fourth Military Medical University, No. 169 West Changle Road, Xi'an, Shaanxi, 710032, P. R. China.
authors.forename: Chao
authors.initials: C
authors.lastname: Xie
authors.affiliation: The Key Laboratory of Space Applied Physics and Chemistry, Ministry of Education and Shaanxi Key Laboratory of Macromolecular Science and Technology, School of Science, Northwestern Polytechnical University, No. 127 West Youyi Road, Xi'an, Shaanxi, 710072, P. R. China.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Fan
authors.affiliation: Frontier Institute of Science and Technology (FIST), Xi'an Jiaotong University, No. 99 Yanxiang Road, Xi'an, Shaanxi, 710054, P. R. China.
authors.forename: Pengfei
authors.initials: P
authors.lastname: Li
mesh_terms: D001386:Azides / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D008970:Molecular Weight; D009636:Norbornanes / Q000737:chemistry*; D058105:Polymerization; D013696:Temperature; D014783:Viscosity
chemical_list: D001386:Azides; D001388:Aziridines; D009636:Norbornanes; C046060:2-norbornene; C033132:aziridine
keywords: azides; cycloaddition; polyaddition; strain; triazolines