Citation: Ling Guo, Yan-Ping Zhang, Hong-Liang Mu, Li Pan, Kai-Ti Wang, Huan Gao, Bin Wang, Zhe Ma, Yue-Sheng Li. Efficient Addition Polymerization of Norbornene with Polar Norbornene Derivatives by Neutral Nickel(II) Catalysts[J]. Chinese Journal of Polymer Science, ;2019, 37(12): 1215-1223. doi: 10.1007/s10118-019-2292-2 shu

Efficient Addition Polymerization of Norbornene with Polar Norbornene Derivatives by Neutral Nickel(II) Catalysts

Ling Guo ^a ,
Yan-Ping Zhang ^a ,
Hong-Liang Mu ^b ,
Li Pan ^a,, ,
Kai-Ti Wang ^c ,
Huan Gao ^a ,
Bin Wang ^a ,
Zhe Ma ^a ,
Yue-Sheng Li ^a,d

a.
Tianjin Key Lab of Composite & Functional Materials, School of Material Science and Engineering, Tianjin University, Tianjin 300350, China
b.
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
c.
School of Materials Science and Engineering, Chongqing University of Technology, Chongqing 400054, China
d.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China

Corresponding author: Li Pan, lilypan@tju.edu.cn
Received Date: 18 April 2019
Revised Date: 7 May 2019
Available Online: 27 June 2019

A series of nickel complexes { 4a : [(2,6-iPr₂C₆H₃)N＝CHC₁₆H₁₂O]Ni(Me)(Py), 4b : [(2,6-iPr₂C₆H₂OCH₃)N＝CHC₁₆H₁₂O]Ni(Me)(Py), 4c : [(2,6-iPr₂C₆H₂Cl)N＝CHC₁₆H₁₂O]Ni(Me)(Py), and 4d : [(2,6-iPr₂C₆H₂CF₃)N＝CHC₁₆H₁₂O]Ni(Me)(Py)} based on β-ketiminato ligands bearing various electron-donating or electron-withdrawing substituents on the para-position of the aniline group were synthesized and unambiguously characterized. The X-ray crystallographic analysis showed that complexes 4b and 4d adopted a near-square-planar geometry, and the anilines bearing a para-OMe or ―CF₃ group were found to situate on the axial position of the metal center. All complexes exhibited high activities up to 1.25 × 10⁷–1.35 × 10⁷ g_PNB·mol_Ni^–1·h^–1 toward norbornene (NBE) addition polymerization (conversion > 91.2% in 2 min) under low loading of B(C₆F₅)₃ (B/Ni = 3) at 30 °C, affording polymers with high molecular weight up to 2.54 × 10⁶–3.18 × 10⁶. Different levels of decrease in catalytic activities could be observed for all catalysts as the reaction temperature increased; 4d bearing a strong electron-withdrawing ―CF₃ group showed the highest activity at 70 °C, while others exhibited notable decrease in catalytic activity with the raise in reaction temperature. Complexes 4a – 4d showed remarkable tolerance to polar groups and could efficiently promote the copolymerization of NBE with its polar derivatives, including NBE bearing small acetate and hydroxyl group, as well as bulky oligomers, yielding copolymers with high functional NBE incorporations. Novel NBE copolymers with high functional comonomer incorporations and improved solubility were obtained in high yields.
- Neutral nickel catalysts,
- Norbornene,
- Norbornene derivatives,
- Vinyl-type polymerization
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