Pd-Salen and Pd-Salan complexes: Characterization and application in styrene polymerization

Inorganic Chemistry Communications

Volumn 14, Issue 4, 2011, Pages 573-577

  Ding, Liqin ^a,b   Chu, Zeng ^a   Chen, Leilei ^a   Lü, Xingqiang ^a,c   Yan, Biao ^a   Song, Jirong ^a   Fan, Daidi ^a   Bao, Feng ^d  

^a NORTHWEST UNIVERSITY   (China)

^b XI'AN SHIYOU UNIVERSITY   (China)

^c FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

^d CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

Electrophilicity or Lewis acidity of active; Pd Salen or Pd Salan complexes; species and catalytic performance; Syndio enriched atactic polystyrene

Indexed keywords

EID: 79952536939     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2011.01.028     Document Type: Article

References (52)

1. (a) C. Barner-Kowollik, G.T. Russell, Chain-length-dependent termination in radical polymerization: subtle revolution in tackling a long-standing challenge, Prog. Polym. Sci. 34 (2009) 1211-1259;
2. (b) S. Carlotti, P. Desbois, V. Warzelhan, A. Deffieux, Retarded anionic polymerization (RAP) of styrene and dienes, Polymer 50 (2009) 3057-3067;
3. (c) S.V. Kostjuk, F. Ganachaud, Cationic polymerization of vinyl monomers in aqueous media: from monofunctional oligomers to long-lived polymer chains, Acc. Chem. Res. 43 (2010) 357-367.
4. (a) D.B. Priddy, Recent advances in styrene polymerization, Adv. Polym. Sci. 111 (1994) 67-114;
5. (b) M. Atiqullah, M. Tinkl, R. Pfaendner, M.N. Akhtar, I. Hussain, Synthesis of functional polyolefins using metallocenes: a comprehensive review, Polym. Rev. 50 (2010) 178-230.
6. (a) J. Schellenberg, H.-J. Leder, Syndiotactic polystyrene: process and applications, Adv. Polym. Technol. 25 (2006) 141-151;
7. (b) S.A. Gursel, L. Gubler, B. Gupta, G.G. Scherer, Radiation grafted membranes, Adv. Polym. Sci. 215 (2008) 157-217;
8. (c) S.V. Levchik, E.D. Weil, New developments in flame retardancy of styrene thermoplastics and foams, Polym. Int. 57 (2008) 431-448;
9. (d) P. Boffetta, H.O. Adami, P. Cole, D. Trichopoulos, J.S. Mandel, Epidemiologic studies of styrene and cancer: a review of the literature, J. Occup. Environ. Med. 51 (2009) 1275-1287.
10. J. Schellenberg, Recent transition metal catalysts for syndiotactic polystyrene, Prog. Polym. Sci. 34 (2009) 688-718.
11. (a) J. Okuda, R. Mulhaupt, Transition metal catalyzed olefin, cycloolefin, and styrene polymerization, Mater. Sci. Technol. 20 (1999) 123-162;
12. (b) Y.V. Kissin, A.J. Brandolini, An alternative route to methylalumoxane: synthesis, structure, and the use of model methylalumoxanes as cocatalysts for transition metal complexes in polymerization reactions, Macromolecules 36 (2003) 18-26;
13. (c) M. Bialek, H. Cramail, A. Deffieux, S.M. Guillaume, Styrene polymerization using nickel(II) complexes as catalysts, Eur. Polym. J. 41 (2005) 2678-2684;
14. (d) L.Z. Xie, H.M. Sun, D.M. Hu, Z.H. Liu, Q. Shen, Y. Zhang, Synthesis and structure of indenylnickel(II) chlorides bearing free N-heterocyclic carbene ligands and their catalysis for styrene polymerization, Polyhedron 28 (2009) 2585-2590.
15. (a) L. Friebe, O. Nuyken, W. Obrecht, Neodymium-based Ziegler/Natta catalysts and their application in diene polymerization, Adv. Polym. Sci. 204 (2006) 1-154;
16. (b) K. Michiue, M. Onda, H. Tanaka, H. Makio, M. Mitani, T. Fujita, Styrene polymerization behavior of phenoxy - imine ligated Ti complexes/MAO: formation of highly isotactic and syndiotactic PS, Macromolecules 41 (2008) 6289-6291;
17. (c) R. Pastorino, C. Capacchione, R. Ferro, S. Milione, A. Grassi, Synthesis of syndiotactic polystyrene macromonomers end capped with bromine atoms: a tool for a new investigation of styrene polymerization mechanism catalyzed by monocyclopentadienyl titanium compounds, Macromolecules 42 (2009) 2480-2487.
18. A.-S. Rodrigues, E. Kirillov, J.-F. Carpentier, Group 3 and 4 single-site catalysts for stereospecific polymerization of styrene, Coord. Chem. Rev. 252 (2008) 2115-2136.
19. (a) J.-F. Lahitte, F. Peruch, S. Plentz-Meneghetti, F. Isel, P.J. Lutz, Homo- and copolymerization of ω-functional polystyrene macromonomers via coordination polymerization, Macromol. Chem. Phys. 203 (2002) 2583-2589;
20. (b) W.-T. Yang, K.-C. Chuang, G.J. Jiang, Homo- and co-polymerization of styrene with 4-chloromethyl styrene by nickel-diimine complex catalysts, Polym. Prepr. 44 (2003) 1004-1005;
21. (c) C.-M. Chi, H.-S. Huang, Metal complexes of chiral binaphthyl Schiff-base ligands and their application in stereoselective organic transformations, Coord. Chem. Rev. 242 (2003) 97-113;
22. (d) Y.F. Li, M.L. Gao, Q. Wu, Styrene polymerization with nickel complexes/methylaluminoxane catalytic system, Appl. Organomet. Chem. 22 (2008) 659-663;
23. (e) J.Z. Li, M. Li, S.Y. Li, L.Y. Shi, C.Y. Ren, D.M. Cui, Y.H. Wang, T. Tang, Styrene polymerization catalyzed by metal porphyrin complex/MAO for in situ synthesizing polystyrene containing air stable π cation radicals, J. Polym. Sci. A. Polym. Chem. 46 (2008) 1240-1248. (Pubitemid 351190440)
24. (a) B. Milani, A. Anzilutti, L. Vicentini, A.S. Santi, E. Zangrando, S. Geremia, G. Mestroni, Bis-chelated palladium(II) complexes with nitrogen-donor chelating ligands are efficient catalyst precursors for the CO/styrene copolymerization reaction, Organometallics 16 (1997) 5064-5075;
25. (b) B. Milani, G. Corso, G. Mestroni, C. Carfagna, M. Formica, R. Seradlia, Highly efficient catalytic system for the CO/styrene copolymerization: toward the stabilization of the active species, Organometallics 19 (2000) 3435-3441;
26. (c) A. Bastero, C. Claver, A. Ruiz, S. Castillon, E. Daura, C. Bo, E. Zangrando, Insights into CO/styrene copolymerization by using Pd(II) catalysts containing modular pyridine-imidazoline ligands, Chem. Eur. J. 10 (2004) 3747-3760;
27. 2Zn-metallocene-MAO systems: synthesis and characterization of poly(styrene-co-p-hydroxystyrene) copolymers, Polymer 48 (2007) 4646-4652;
28. (e) C. Carfagna, G. Gatti, P. Paoli, P. Rossi, Mechanism for stereoblock isotactic CO/styrene copolymerization promoted by aryl α-diimine Pd(II) Catalysts: a DFT study, Organometallics 28 (2009) 3212-3217.
29. J.R. Ascenso, A.R. Dias, P.T. Gomes, C.C. Romao, A. Revillon, I. Tkatchenko, Cationic benzyl nickel complexes as homogeneous catalysts for styrene oligomerization, Polyhedron 8 (1989) 2449-2457.
30. H.Y. Gao, L.X. Pei, K.M. Song, Q. Wu, Styrene polymerization with novel anilido-imino nickel complexes/MAO catalytic system: catalytic behavior, microstructure of polystyrene and polymerization mechanism, Eur. Polym. J. 43 (2007) 908-914. (Pubitemid 46273404)
31. (a) R.K. O' Reilly, V.C. Gibson, A.J.P. White, D.J. Williams, Design of highly active iron-based catalysts for atom transfer radical polymerization: tridentate salicylaldiminato ligands affording near ideal Nernstian behavior, J. Am. Chem. Soc. 125 (2003) 8450-8451;
32. (b) R. Ferro, S. Milione, V. Bertolasi, C. Capacchione, A. Grassi, Iron complexes of bis(oxazoline) ligand as novel catalysts for efficient atom transfer radical polymerization of styrene, Macromolecules 40 (2007) 8544-8546. (Pubitemid 350241353)
33. D.A. Atwood, M.J. Harvey, Group 13 compounds incorporating Salen ligands, Chem. Rev. 101 (2001) 37-52.
34. (a) N.S. Venkataramanan, S. Natarajan, G. Kuppuraj, S. Rajagopai, Metal-Salen complexes as efficient catalysts for the oxygenation of heteroatom containing organic compounds-synthetic and mechanistic aspects, Coord. Chem. Rev. 249 (2005) 1249-1268;
35. (b) C. Baleizao, H. Garcia, Chiral Salen complexes: an overview to recoverable and reusable homogeneous and heterogeneous catalysts, Chem. Rev. 106 (2006) 3987-4043;
36. 2, Chem. Rev. 107 (2007) 2388-2410.
37. K.C. Gupta, A.K. Sutar, Catalytic activities of Schiff base transition metal complexes, Coord. Chem. Rev. 252 (2008) 1420-1450.
38. (a) R. Ma, Y.B. Hou, F. Bao, Recent progress in the vinylic polymerization and copolymerization of norbornene catalyzed by transition metal catalysts, Polym. Rev. 49 (2009) 249-287;
39. 2+ complex for the vinylic-type polymerization of norbornene, J. Inorg. Organomet. Polym. 20 (2010) 235-241.
40. (a) A. Cohen, A. Yeori, J. Kopilov, I. Goldberg, M. Kol, Construction of C1-symmetric zirconium complexes by the design of new Salan ligands: coordination chemistry and preliminary polymerisation catalysis studies, Chem. Commun. (2008) 2149-2151;
41. (b) A. Cohen, J. Kopilov, I. Goldberg, M. Kol, C1-symmetric zirconium complexes of [ONNO]-type Salan ligands: accurate control of catalyst activity, iso-specificity, and molecular weight in 1-hexene polymerization, Organometallics 28 (2009) 1391-1405.
42. M. Bialek, K. Czaja, E. Szydlo, Transition metal complexes of tetradentate and bidentate Schiff bases as catalysts for ethylene polymerization: effect of transition metal and cocatalyst, J. Polym. Sci. A. Polym. Chem. 47 (2009) 565-575.
43. (a) C. Capacchione, R. Manivannan, M. Barone, K. Beckerle, R. Centore, L. Oliva, A. Proro, A. Tuzi, T.P. Spaniol, J. Okuda, Isospecific styrene polymerization by chiral titanium complexes that contain a tetradentate [OSSO]-type bis (phenolato) ligand, Organometallics 24 (2005) 2971-2982;
44. (b) M. Strianese, M. Lambert, M. Mazzeo, C. Pellecchia, A comparative study on the polymerization of olefins catalyzed by Salen and Salan zirconium complexes, Macromol. Chem. Phys. 209 (2008) 585-592.
45. 2 and propylene oxide catalyzed by chiral chromium Salan complexes, J. Polym. Sci. A. Polym. Chem. 46 (2008) 6102-6113;
46. (b) D.Y. Rao, B. Li, R. Zhang, H. Wang, X.B. Lü, Binding of 4-(N, N-dimethylamino) pyridine to Salen- and Salan-Cr(III) cations: a mechanistic understanding on the difference in their catalytic activity for CO2/epoxide copolymerization, Inorg. Chem. 48 (2009) 2830-2836.
47. E.J. Baerends, et al., Theoretical Chemistry, ADF SCM, Vrije Universiteit, Amsterdam, Netherland, 2005.
48. M.L. Kantam, S. Ghosh, K. Aziz, B. Sreedhar, B.M. Choudary, Nanoparticle supported bis -cyclopentadienyl zirconium dichloride catalysts for styrene polymerization, J. Mol. Catal. A. Chem. 240 (2005) 103-108. (Pubitemid 41231729)
49. S. Ghosh, Influence of cocatalyst on the stereoselectivity and productivity of styrene polymerization reactions, J. Polym. Res. 16 (2009) 117-124.
50. T.B.L. Nguyen, T.D.H. Nguyen, S.K. Noh, W.S. Lyoo, D.H. Lee, Y. Kim, Preparation of new dinuclear half-titanocene complexes with ortho- and meta-xylene linkages and investigation of styrene polymerization, J. Organomet. Chem. 694 (2009) 3438-3443.
51. S.X. Yu, X.H. He, Y.W. Chen, Y.M. Liu, S.G. Hong, Q. Wu, Polymerization of styrene using bis(β-ketoamino)nickel(II)/methylaluminoxane catalytic systems, J. Appl. Polym. Sci. 105 (2007) 500-509. (Pubitemid 46896612)
52. F. Bao, R. Ma, X.Q. Lü, G.Q. Gui, Q. Wu, Structures and styrene polymerization activities of a series of nickel complexes bearing ligands of pyrazolone derivatives, Appl. Organomet. Chem. 20 (2006) 32-38. (Pubitemid 43082347)