Styrene-containing Phosphine-sulfonate Ligands for Nickel- and Palladium-catalyzed Ethylene Polymerization
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ARTICLE
POLYMER SCIENCE
https://doi.org/10.1007/s10118-021-2509-z Chinese J. Polym. Sci.
Styrene-containing Phosphine-sulfonate Ligands for Nickel- and Palladium-catalyzed Ethylene Polymerization Shabnam Behzadia,†, Chen Zoua,†, Bang-Pei Yanga, Chen Tanb*, and Chang-Le Chena* a Chinese Academy of Sciences Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Sciences at the Microscale, Department of Polymer
Science and Engineering, University of Science and Technology of China, Hefei 230026, China b Institutes of Physical Science and Information Technology, Key Laboratory of Structure and Functional Regulation of Hybrid Materials of Ministry of Education, Anhui University, Hefei 230026, China
Electronic Supplementary Information Abstract A series of phosphine-sulfonate ligands bearing 2-, 3- and 4-vinylphenyl on the phosphorus atom were designed, synthesized, characterized and investigated in Ni- and Pd-catalyzed ethylene polymerization. The structure of the phosphine-sulfonate Pd complex bearing 2-vinylphenyl on the phosphorus atom showed 2,1-insertion for the 2-vinyl group. The phosphine-sulfonate Ni complex bearing 2-vinylphenyl resulted in significantly increased thermal stability and polyethylene molecular weights (Mn = 3.69×104 g·mol−1 at 80 °C) versus the counterparts bearing 3-/4-vinyl groups as well as previously reported phosphine-sulfonate Ni complexes bearing bulky biaryl substituents. Keywords Phosphine-sulfonate; Ethylene polymerization; Steric effect; Palladium; Nickel Citation: Behzadi, S.; Zou, C.; Yang, B. P.; Tan, C.; Chen, C. L. Styrene-containing phosphine-sulfonate ligands for nickel- and palladium-catalyzed ethylene polymerization. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-021-2509-z
INTRODUCTION Late transition metal catalysts have been playing increasingly important roles in the field of olefin polymerization.[1–15] Nickel compounds were initially known as a "poison" for olefin polymerization, since the famous nickel effect was observed by Ziegler and co-workers.[16] Now, the situation has changed dramatically,[17] since many nickel catalysts have been developed for producing high molecular weight polyethylenes, such as α-diimine[1,18–32] (Chart 1, I), salicylaldimine[33–36] (Chart 1, II), pyridine-imine[37−39] (Chart 1, III), 2-iminopyridine-N-oxide[40] (Chart 1, IV) and α-iminoketone[41] (Chart 1, V) nickel catalysts. Moreover, some phosphine-ligand-based nickel catalysts exhibit the capabilities of producing high molecular weight polyethylenes, including tri-1-adamantylphosphine[42] (Chart 1, VI) and some SHOP (shell higher olefin process) type[43–46] (Chart 1, VII) nickel catalysts. To improve catalytic performances of catalysts, many efforts have been directed towards modifying ligand structures by introducing various substituents. Many systematic researches on either steric or electronic effects of substituents have been reported.[1–3,9–15] For instance, the dicyclohexyl
* Corresponding authors, E-mail: [email protected]
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