Citation: Chen Tan, Wen-Min Pang, Chang-Le Chen. A Phenol-containing α-Diimine Ligand for Nickel- and Palladium-Catalyzed Ethylene Polymerization[J]. Chinese Journal of Polymer Science, ;2019, 37(10): 974-980. doi: 10.1007/s10118-019-2232-1 shu

A Phenol-containing α-Diimine Ligand for Nickel- and Palladium-Catalyzed Ethylene Polymerization

Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China

Corresponding author: Chang-Le Chen, changle@ustc.edu.cn
Received Date: 26 December 2018
Revised Date: 21 January 2019
Available Online: 1 March 2019

A phenol-containing dibenzhydryl-based α-diimine ligand bearing hydroxy group on para-position of aniline moiety was designed, synthesized, and investigated in Ni- and Pd-catalyzed ethylene polymerization. The Ni complex bearing hydroxy groups resulted in not only high polyethylene molecular weight (M_n up to 1.5 × 10⁶), but also significantly increased melting temperature (T_m up to 123 °C) and greatly decreased branching density (33/1000C) versus the Ni catalyst bearing OMe group on para-position of aniline moiety. This is consistent with the hypothesis that the deprotonation of the phenol moiety generated a phenoxide bearing strong electron-donating O⁻ substituent by methylaluminoxane (MAO) cocatalyst. The Pd complexes bearing hydroxy groups exhibited similar catalytic properties to those of the Pd catalyst bearing OMe groups did.
- α-Diimine,
- Ethylene polymerization,
- Electronic effect,
- Palladium,
- Nickel
1. [1]
  Huynh, H. V. Electronic properties of N-heterocyclic carbenes and their experimental determination. Chem. Rev. 2018, 118, 9457-9492. doi: 10.1021/acs.chemrev.8b00067
2. [2]
  Li, Y.; Zhang, Y. Y.; Hu, L. F.; Zhang, X. H.; Du, B. Y.; Xu, J. T. Carbon dioxide-based copolymers with various architectures. Prog. Polym. Sci. 2018, 82, 120-157. doi: 10.1016/j.progpolymsci.2018.02.001
3. [3]
  Van Zee, N. J.; Sanford, M. J.; Coates, G. W. Electronic effects of aluminum complexes in the copolymerization of propylene oxide with tricyclic anhydrides: Access to well-defined, functionalizable aliphatic polyesters. J. Am. Chem. Soc. 2016, 138, 2755-2761. doi: 10.1021/jacs.5b12888
4. [4]
  Xu, L.; Hilton, M. J.; Zhang, X.; Norrby, P. O.; Wu, Y. D.; Sigman, M. S.; Wiest, O. Mechanism, reactivity, and selectivity in palladium-catalyzed redox-relay Heck arylations of alkenyl alcohols. J. Am. Chem. Soc. 2014, 136, 1960-1967. doi: 10.1021/ja4109616
5. [5]
  Cusso, O.; Garcia-Bosch, I.; Ribas, X.; Lloret-Fillol, J.; Costas, M. Asymmetric epoxidation with H₂O₂ by manipulating the electronic properties of non-heme iron catalysts. J. Am. Chem. Soc. 2013, 135, 14871-14878. doi: 10.1021/ja4078446
6. [6]
  Chen, M. S.; White, M. C. A predictably selective aliphatic C―H oxidation reaction for complex molecule synthesis. Science 2007, 318, 783-787. doi: 10.1126/science.1148597
7. [7]
  Wang, F. Z.; Tian, S. S.; Lia, R. P.; Li, W. M.; Chen, C. L. Ligand steric effects on naphthyl-α-diimine nickel catalyzed α-olefin polymerization. Chinese J. Polym. Sci. 2018, 36, 157-162. doi: 10.1007/s10118-018-2038-6
8. [8]
  Kaiser, J. M.; Long, B. K. Recent developments in redox-active olefin polymerization catalysts. Coord. Chem. Rev. 2018, 372, 141-152. doi: 10.1016/j.ccr.2018.06.007
9. [9]
  Ito, S. Palladium-catalyzed homo- and copolymerization of polar monomers: Synthesis of aliphatic and aromatic polymers. Bull. Chem. Soc. Jpn. 2018, 91, 251-261. doi: 10.1246/bcsj.20170347
10. [10]
  Si, G. F.; Na, Y. N.; Chen, C. L. Ethylene (co)oligomerization by phosphine‐pyridine based palladium and nickel catalysts. ChemCatChem 2018, 10, 5135–5140. doi: 10.1002/cctc.201800957
11. [11]
  Fu, X.; Zhang, L.; Tanaka, R.; Shiono, T.; Cai, Z. Highly robust nickel catalysts containing anilinonaphthoquinone ligand for copolymerization of ethylene and polar monomers. Macromolecules 2017, 50, 9216-9221. doi: 10.1021/acs.macromol.7b01947
12. [12]
  Jian, Z. B. Synthesis of functionalized polyolefins: Design from catalysts to polar monomers. Acta Polymerica Sinica (in Chinese) 2018, 1359-1371.
13. [13]
  Ma, Z.; Yang, W.; Sun, W. H. Recent progress on transition metal (Fe, Co, Ni, Ti and V) complex catalysts in olefin polymerization with high thermal stability. Chinese J. Chem. 2017, 35, 531-540. doi: 10.1002/cjoc.v35.5
14. [14]
  Song, X. Y.; Ma, Q.; Yuan, H. B.; Cai, Z. G. Synthesis of hydroxy-functionalized ultrahigh molecular weight polyethylene using fluorenylamidotitanium complex. Chinese J. Polym. Sci. 2018, 36, 171-175. doi: 10.1007/s10118-018-2046-6
15. [15]
  Zhang, D.; Chen, C. L. Influence of polyethylene glycol unit on palladium and nickel catalyzed ethylene polymerization and copolymerization. Angew. Chem. Int. Ed. 2017, 56, 14672–14676. doi: 10.1002/anie.201708212
16. [16]
  Chen, M.; Chen, C. L. Polar functionalized polyolefins: New catalysts, new modulation strategies and new materials. Acta Polymerica Sinica (in Chinese) 2018, 1372-1384.
17. [17]
  Guo, L. H.; Liu, W.; Chen, C. L. Late transition metal catalyzed α-olefin polymerization and copolymerization with polar monomers. Mater. Chem. Front. 2017, 1, 2487-2494. doi: 10.1039/C7QM00321H
18. [18]
  Chen, C. L. Designing transition metal catalysts for olefin polymerization and copolymerization: Beyond electronic and steric tuning. Nat. Rev. Chem. 2018, 2, 6-14. doi: 10.1038/s41570-018-0003-0
19. [19]
  Zhao, M. H.; Chen, C. L. Accessing multiple catalytically active states in redox controlled olefin polymerization. ACS Catal. 2017, 7, 7490-7494. doi: 10.1021/acscatal.7b02564
20. [20]
  Guo, L. H.; Dai, S. Y.; Sui, X. L.; Chen, C. L. Palladium and nickel catalyzed chain walking olefin polymerization and copolymerization. ACS Catal. 2016, 6, 428-441. doi: 10.1021/acscatal.5b02426
21. [21]
  Chen, C. L. Redox controlled polymerization and copolymerization. ACS Catal. 2018, 8, 5506–5514. doi: 10.1021/acscatal.8b01096
22. [22]
  Zuideveld, M. A.; Wehrmann, P.; Röhr, C.; Mecking, S. Remote substituents controlling catalytic polymerization by very active and robust neutral nickel(II) complexes. Angew. Chem. Int. Ed. 2004, 43, 869-873. doi: 10.1002/(ISSN)1521-3773
23. [23]
  Gao, H. Y.; Ke, Z. F.; Pei, L. X.; Song, K. M.; Wu, Q. Drastic ligand electronic effect on anilido-imino nickel catalysts toward ethylene polymerization. Polymer 2007, 48, 7249-7254. doi: 10.1016/j.polymer.2007.10.022
24. [24]
  Wucher, P.; Goldbach, V.; Mecking, S. Electronic influences in phosphinesulfonato palladium(II) polymerization catalysts. Organometallics 2013, 32, 4516-4522. doi: 10.1021/om400297x
25. [25]
  Chen, M.; Chen, C. L. Rational design of high-performance phosphine sulfonate nickel catalysts for ethylene polymerization and copolymerization with polar monomers. ACS Catal. 2017, 7, 1308-1312. doi: 10.1021/acscatal.6b03394
26. [26]
  Liang, T.; Chen, C. L. Position makes the difference: Electronic effects in nickel-catalyzed ethylene polymerizations and copolymerizations. Inorg. Chem. 2018, 57, 14913-14919. doi: 10.1021/acs.inorgchem.8b02687
27. [27]
  Gao, J. X.; Yang, B. P.; Chen, C. L. Sterics versus electronics: Imine/phosphine-oxide-based nickel catalysts for ethylene polymerization and copolymerization. J. Catal. 2019, 369, 233-238. doi: 10.1016/j.jcat.2018.11.007
28. [28]
  Popeney, C. S.; Levins, C. M.; Guan, Z. Systematic investigation of ligand substitution effects in cyclophane-based nickel(II) and palladium(II) olefin polymerization catalysts. Organometallics 2011, 30, 2432-2452. doi: 10.1021/om200193r
29. [29]
  Popeney, C.; Guan Z. Ligand electronic effects on late transition metal polymerization catalysts. Organometallics 2005, 24, 1145-1155. doi: 10.1021/om048988j
30. [30]
  Popeney, C. S.; Guan Z. Effect of ligand electronics on the stability and chain transfer rates of substituted Pd(II) α-diimine catalysts. Macromolecules 2010, 43, 4091-4097. doi: 10.1021/ma100220n
31. [31]
  Dai, S. Y.; Sui, X. L.; Chen, C. L. Highly robust palladium(II) α-diimine catalysts for slow-chain-walking polymerization of ethylene and copolymerization with methyl acrylate. Angew. Chem. Int. Ed. 2015, 54, 9948-9953. doi: 10.1002/anie.201503708
32. [32]
  Guo, L. H.; Dai, S. Y.; Chen, C. L. Investigations of the ligand electronic effects on α-diimine nickel(II) catalyzed ethylene polymerization. Polymers 2016, 8, 37-46. doi: 10.3390/polym8020037
33. [33]
  Dai, S. Y.; Chen, C. L. Direct synthesis of functionalized high-molecular-weight polyethylene by copolymerization of ethylene with polar monomers. Angew. Chem. Int. Ed. 2016, 55, 13281-13285. doi: 10.1002/anie.201607152
34. [34]
  Dai, S. Y.; Chen, C. L. Palladium-catalyzed direct synthesis of various branched, carboxylic acid-functionalized polyolefins: Characterization, derivatization, and properties. Macromolecules 2018, 51, 6818-6824. doi: 10.1021/acs.macromol.8b01261
35. [35]
  Na, Y. N.; Dai, S. Y.; Chen, C. L. Direct synthesis of polar-functionalized linear low-density polyethylene (LLDPE) and low-density polyethylene (LDPE). Macromolecules 2018, 51, 4040-4048. doi: 10.1021/acs.macromol.8b00467
36. [36]
  Zou, C.; Dai, S. Y.; Chen, C. L. Ethylene polymerization and copolymerization using nickel 2-iminopyridine-N-oxide catalysts: Modulation of polymer molecular weights and molecular-weight distributions. Macromolecules 2018, 51, 49-56. doi: 10.1021/acs.macromol.7b02156
37. [37]
  Fang, J.; Sui, X. L.; Li, Y. G.; Chen, C. L. Synthesis of polyolefin elastomers from unsymmetrical α-diimine nickel catalyzed olefin polymerization. Polym. Chem. 2018, 9, 4143-4149. doi: 10.1039/C8PY00725J
38. [38]
  Zhou, S. X.; Chen, C. L. Synthesis of silicon-functionalized polyolefins by subsequent cobalt-catalyzed dehydrogenative silylation and nickel-catalyzed copolymerization. Sci. Bull. 2018, 63, 441-445. doi: 10.1016/j.scib.2018.02.021
39. [39]
  Lian, K.; Zhu, Y.; Li, W.; Dai, S. Y.; Chen, C. L. Direct synthesis of thermoplastic polyolefin elastomers from nickel-catalyzed ethylene polymerization. Macromolecules 2017, 50, 6074-6080. doi: 10.1021/acs.macromol.7b01087
40. [40]
  Sui, X. L.; Hong, C. W.; Pang, W. M.; Chen, C. L. Unsymmetrical α-diimine palladium catalysts and their properties in olefin (co) polymerization. Mater. Chem. Front. 2017, 1, 967-972. doi: 10.1039/C6QM00235H
41. [41]
  Hansch, C.; Leo, A.; Taft, R. W. A survey of Hammett substituent constants and resonance and field parameters. Chem. Rev. 1991, 91, 165-195. doi: 10.1021/cr00002a004
42. [42]
  Pawlicki, M.; Collins, H. A.; Denning, R. G.; Anderson, H. L. Two-photon absorption and the design of two-photon dyes. Angew. Chem. Int. Ed. 2009, 48, 3244-3266. doi: 10.1002/anie.v48:18
43. [43]
  Tian, Y.; Chen, C. Y.; Yang, C. C.; Young, A. C.; Jang, S. H.; Chen, W. C.; Alex, K. Y. J. 2-(2′-Hydroxyphenyl) benzoxazole-containing two-photon-absorbing chromophores as sensors for zinc and hydroxide ions. Chem. Mater. 2008, 20, 1977-1987. doi: 10.1021/cm702527m
44. [44]
  Yang, P.; Zhao, J.; Wu, W.; Yu, X.; Liu, Y. Accessing the long-lived triplet excited states in bodipy-conjugated 2-(2-hydroxyphenyl) benzothiazole/benzoxazoles and applications as organic triplet photosensitizers for photooxidations. J. Org. Chem. 2012, 77, 6166-6178. doi: 10.1021/jo300943t
45. [45]
  Khan, S. A.; Azam, S. First principle investigation of electronic structure, chemical bonding and optical properties of tetrabarium gallium trinitride oxide single crystal. Mater. Res. Bull. 2015, 70, 436-441. doi: 10.1016/j.materresbull.2015.04.064
46. [46]
  Takagi, S.; Orimo, S. Recent progress in hydrogen-rich materials from the perspective of bonding flexibility of hydrogen. Scripta Mater. 2015, 109, 1-5. doi: 10.1016/j.scriptamat.2015.07.024
47. [47]
  Pauling, L. in The nature of the chemical bond, Cornell University Press, Ithaca, NY, 1967.
48. [48]
  Riilke, R. E.; Ernsting, J. M.; Spelt, A. L.; Elsevier, C. J.; van Leeuwelqs, R. W. N. M.; Vrieze, K. NMR study on the coordination behavior of dissymmetric terdentate trinitrogen ligands on methylpalladium(II) compounds. Inorg. Chem. 1993, 32, 5769-5778. doi: 10.1021/ic00077a020
49. [49]
  Gomes, C. S. B.; Costa, S. I.; Silva, L. C.; Jimenez-Tenorio, M.; Valerga, P.; Puerta, M. C.; Gomes, P. T. Cationic R-substituted-indenyl nickel(II) complexes of arsine and stibine ligands: Synthesis, characterization, and catalytic behavior in the oligomerization of styrene. Eur. J. Inorg. Chem. 2018, 597-607.
50. [50]
  Kaliner, M.; Strassner, T. Tunable aryl alkyl ionic liquids with weakly coordinating bulky borate anion. Tetrahedron Lett. 2016, 57, 3453-3456. doi: 10.1016/j.tetlet.2016.06.082
51. [51]
  Pei, L.; Liu, F.; Liao, H.; Gao, J.; Zhong, L.; Gao, H.; Wu, Q. Synthesis of polyethylenes with controlled branching with α-diimine nickel catalysts and revisiting formation of long-chain branching. ACS Catal. 2018, 8, 1104-1113. doi: 10.1021/acscatal.7b03282
52. [52]
  Zhong, S.; Tan, Y.; Zhong, L.; Gao, J.; Liao, H.; Jiang, L.; Gao, H.; Wu, Q. Precision synthesis of ethylene and polar monomer copolymers by palladium-catalyzed living coordination copolymerization. Macromolecules 2017, 50, 5661-5669. doi: 10.1021/acs.macromol.7b01132
53. [53]
  Zhong, L.; Li, G.; Liang, G.; Gao, H.; Wu, Q. Enhancing thermal stability and living fashion in α-diimine-nickel-catalyzed (co) polymerization of ethylene and polar monomer by increasing the steric bulk of ligand backbone. Macromolecules 2017, 50, 2675-2682. doi: 10.1021/acs.macromol.7b00121
54. [54]
  Liao, H.; Zhong, L.; Xiao, Z.; Zheng, T.; Gao, H.; Wu, Q. α-Diamine nickel catalysts with nonplanar chelate rings for ethylene polymerization. Chem. Eur. J. 2016, 22, 14048-14055. doi: 10.1002/chem.201602467
55. [55]
  Hu, H.; Gao, H.; Chen, D.; Li, G.; Tan, Y.; Liang, G.; Zhu, F.; Wu, Q. Ligand-directed regioselectivity in amine–imine nickel-catalyzed 1-hexene polymerization. ACS Catal. 2015, 5, 122-128. doi: 10.1021/cs501081a
56. [56]
  Hu, H.; Zhang, L.; Gao, H.; Zhu, F.; Wu, Q. Design of thermally stable amine-imine nickel catalyst precursors for living polymerization of ethylene: Effect of ligand substituents on catalytic behavior and polymer properties. Chem. Eur. J. 2014, 20, 3225-3233. doi: 10.1002/chem.201303813
57. [57]
  Liu, J.; Chen, D.; Wu, H.; Xiao, Z.; Gao, H.; Zhu, F.; Wu, Q. Polymerization of α-olefins using a camphyl α-diimine nickel catalyst at elevated temperature. Macromolecules 2014, 47, 3325-3331. doi: 10.1021/ma5004634
58. [58]
  Zai, S.; Gao, H.; Huang, Z.; Hu, H.; Wu, H.; Wu, Q. Substituent effects of pyridine-amine nickel catalyst precursors on ethylene polymerization. ACS Catal. 2012, 2, 433-440. doi: 10.1021/cs200593c
59. [59]
  Gao, H.; Liu, X.; Tang, Y.; Pan, J.; Wu, Q. Living/controlled polymerization of 4-methyl-1-pentene with α-diimine nickel-diethylaluminium chloride: Effect of alkylaluminium cocatalysts. Polym. Chem. 2011, 2, 1398-1403. doi: 10.1039/c1py00052g
60. [60]
  Liu, F. S.; Hu, H. B.; Xu, Y.; Guo, L. H.; Zai, S. B.; Song, K. M.; Gao, H. Y.; Zhang, L.; Zhu, F. M.; Wu, Q. Thermostable α-diimine nickel(II) catalyst for ethylene polymerization: Effects of the substituted backbone structure on catalytic properties and branching structure of polyethylene. Macromolecules 2009, 42, 7789-7796. doi: 10.1021/ma9013466
61. [61]
  CCDC 1887662 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
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