New half-sandwich zirconium(IV) complexes containing salicylaldimine ligands: Synthesis, characterizations and catalytic properties

Abstract

Two new half-sandwich zirconium(IV) complexes bearing salicylaldimine ligands of the type Cp*Zr[2- ^tBu-4-R-6-(CH=N ⁱPr)C₆H₂O]Cl₂[R=H(1), ^tBu(2)] were prepared by the reaction of Cp*ZrCl₃ with the corresponding lithium of salicylaldimine ligands 2- ^tBu-4-R-6-(CH=N ⁱPr)C₆H₂OLi[R=H(LiLa), ^tBu(LiLb)]. Complexes 1 and 2 were characterized by ¹H NMR, ¹³C NMR spectroscopy and elemental analysis. When activated with Al ⁱBu₃ and Ph₃CB(C₆F₅)₄, both complexes 1 and 2 exhibited reasonable catalytic activities for ethylene polymerization, producing polyethylenes with moderate molecular weight. Complexes 1 and 2 also exhibited reasonable catalytic activities for ethylene copolymerization with 1-hexene, producing poly(ethylene-co-1-hexene)s with moderate molecular weight and reasonable 1-hexene content.

Keywords

Zirconium complex / Metallocene catalyst / Ethylene polymerization / Olefin copolymerization

References

[1] McKnight A L, Waymouth R M. Chem. Rev., 1998, 98: 2587.

[2] Alt H G, Köppl A. Chem. Rev., 2000, 100: 1205.

[3] Kaminsky W, Arndt-Rosenau M. Applied Homogeneous Catalysis with Organometallic Compounds, 2002 2nd Ed. Weinheim: Wiley-VCH Verlag GmbH.

[4] Motta A, Fragala I L, Marks T J. J. Am. Chem. Soc., 2007, 129: 7327.

[5] Brintzinger H H, Fischer D, Mülhaupt R, Rieger B, Waymouth R M. Angew. Chem. Int. Ed. Engl., 1995, 34: 1143.

[6] Kaminsky W, Arndt M. Adv. Polym. Sci., 1997, 127: 143.

[7] Kaminsky W. Macromol. Chem. Phys., 1996, 197: 3907.

[8] Britovsek G J P, Gibson V C, Wass D F. Angew. Chem. Int. Ed. Engl., 1999, 38: 428.

[9] Chen Y X, Fu P F, Stern C L, Marks T J. Organometallics, 1997, 16: 5958.

[10] Sinn H, Kaminsky W. Adv. Organomet. Chem., 1980, 18: 99.

[11] Chen Y X, Marks T J. Organometallics, 1997, 16: 3649.

[12] Goretzki R, Fink G. Macromol. Rapid Commun., 1998, 19: 511.

[13] Hagihara H, Tsuchihara K, Takeuchi K, Murata M, Ozaki H, Shiono T. J. Polym. Sci. Part A: Polym. Chem., 2004, 42: 52.

[14] Hauptman E, Waymouth R M, Ziller J. J. Am. Chem. Soc., 1995, 117: 11586.

[15] Lin S, Waymouth R M. Acc. Chem. Res., 2002, 35: 765.

[16] Liu K, Wu Q, Gao W, Mu Y, Ye L. Eur. J. Inorg. Chem., 2011, 1901.

[17] Devore D D, Maks T J, Deck P A, Stern C L. Organometallics, 1995, 14: 3132.

[18] du Plooy K E, Moll U, Wocadlo S, Massa W, Okuda J. Organometallics, 1995, 14: 3129.

[19] Nomura K, Naga N, Miki M, Yanagi K, Imai A. Organometallics, 1998, 17: 2152.

[20] Nomura K, Oya K, Komatsu T, Imanishi Y. Macromolecules, 2000, 33: 3187.

[21] Nomura K, Liu J, Fujiki M, Takemoto A. J. Am. Chem. Soc., 2007, 129: 14170.

[22] Gòmez R, Duchateau R, Chernega A N, Teuben J H, Edelmann F T. J. Organomet. Chem., 1995, 491: 153.

[23] Antiñolo A, Carrillo-Hermosilla F, Corrochano A, Fernández-Baeza J, Lara-Sanchez A, Ribeiro M R, Lanfranchi M, Otero A, Pellinghelli M A, Portela M F, Santos J V. Organometallics, 2000, 19: 2837.

[24] Liu J Y, Liu S R, Li B X, Li Y G, Li Y S. Organometallics, 2011, 30: 4052.

[25] Bott R K J, Hughes D L, Schormann M, Bochmann M, Lancaster S J. J. Organomet. Chem., 2003, 665: 135.

[26] Huang W, Sun X, Ma H, Huang J. Inorg. Chim. Acta, 2010, 363: 2009.

[27] Cabrera A R, Schneider Y, Valderrama M, Fröhlich R, Kehr G, Erker G, Rojas R S. Organometallics, 2010, 29: 6104.

[28] Vallmerhaus R, Rahim M, Tomaszewski R, Xin S, Taylor N J, Collins S. Organometallics, 2000, 19: 2161.

[29] Liu K, Wu Q, Luo X, Gao W, Mu Y. Dalton Trans., 2012, 41: 3461.

[30] Liu K, Wu Q, Gao W, Mu Y. Dalton Trans., 2011, 40: 4715.

[31] Irigoyen A M, Martin A, Mena M, Palacios F, Yelamos C. J. Organomet. Chem., 1995, 494: 255.

[32] Shah S A A, Dorn H, Voigt A, Roesky H W, Parisini E, Schmidt H G, Noltemeyer M. Organometallics, 1996, 15: 3176.

[33] Hu P, Wang F, Jin G X. Organometallics, 2011, 30: 1008.

[34] Perrin D D, Perrin D R. Purification of Laboratory Chemicals, 1980, New York: Pergamon.

[35] Wolczanski P T, Bercaw J E. Organometallics, 1982, 1: 793.

[36] Massey A G, Park A J. J. Organomet. Chem., 1966, 5: 218.

[37] Chien J C W, Tsai W M, Rasch M D. J. Am. Chem. Soc., 1991, 113: 8570.

[38] Xu T, Mu Y, Gao W, Ni J, Ye L, Tao Y. J. Am. Chem. Soc., 2007, 129: 2236.

[39] Qu Z, Li X, Pang X, Duan R, Gao Bo, Chen X. Chem. J. Chinese Universities, 2014, 35(3): 626.

[40] Gao L, Yu J. Chem. J. Chinese Universities, 2013, 34(1): 108.

[41] Yang W L, Li Q, Wei T B, Zhang Y M, Lin Q, Shi B B, Zhang P. Chem. Res. Chinese Universities, 2013, 29(2): 236.

[42] Hayes P G, Welch G C, Emslie D J H, Noack C L, Piers W E, Parvez M. Organometallics, 2003, 22: 1577.

[43] Scollard J D, McConville D H, Payne N C. Macromolecules, 1996, 29: 5241.

[44] Liu K, Wu Q, Mu X, Gao W, Mu Y. Polyhedron, 2013, 52: 222.

[45] Nomura K, Naga N, Miki M, Yanagi K. Macromolecules, 1998, 31: 7588.

[46] Nomura K, Naga N, Takaoki K. Macromolecules, 1998, 31: 8009.

[47] Randall J C. J. Macromol. Sci. Rev. Macromol. Chem. Phys., 1989, C29: 201.