Iminopyridine Manganese and Nickel Complexes: Synthesis, Characterization and Behavior in the Polymerization of 1,3-Butadiene

Giovanni Ricci; Benedetta Palucci; Simona Losio; Anna Sommazzi; Francesco Masi; Guido Pampaloni; Massimo Guelfi

doi:10.1007/s10118-024-3233-2

Your Location：

Home >

Browse articles >

Iminopyridine Manganese and Nickel Complexes: Synthesis, Characterization and Behavior in the Polymerization of 1,3-Butadiene

RESEARCH ARTICLE | Updated：2024-11-14

- Iminopyridine Manganese and Nickel Complexes: Synthesis, Characterization and Behavior in the Polymerization of 1,3-Butadiene
- Chinese Journal of Polymer Science Vol. 42, Pages: 1-7(2024)
- Affiliations：
  
  a.CNR-Istituto di Scienze e Tecnologie "Chimiche" "Giulio Natta" (SCITEC), Via A. Corti 12, I-20133 Milano, Italy
  b.Scientific Advisor, Viale Giovanni XXIII 34, I-28100 Novara, Italy
  c.Scientific Advisor, Via Galvani 7, I-26866 Sant’Angelo Lodigiano (LO), Italy
  d.Scientific Advisor, Via E. Fiumalbi 29, I-56025 Pontedera (PI), Italy
  e.Università di Pisa, Dipartimento di Chimica e Chimica Industriale, Via Moruzzi 13, I-56124 Pisa, Italy
  f.Centro per l'Integrazione della Strumentazione Scientifica dell'Università di Pisa (C.I.S.U.P.), Università di Pisa, I-56124 Pisa, Italy
- Author bio：
  
  giovanni.ricci@scitec.cnr.it
- Funds：
- DOI：10.1007/s10118-024-3233-2
  CLC：
- Published：2024-09，
  
  Published Online：14 November 2024，
  
  Received：25 July 2024，
  
  Revised：04 September 2024，
  
  Accepted：05 September 2024
- Accepted：
Scan QR Code
Ricci, G.; Palucci, B.; Losio, S.; Sommazzi, A.; Masi, F.; Pampaloni, G.; Guelfi, M. Iminopyridine manganese and nickel complexes: synthesis, characterization and behavior in the polymerization of 1,3-butadiene. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-024-3233-2

Giovanni Ricci, Benedetta Palucci, Simona Losio, et al. Iminopyridine Manganese and Nickel Complexes: Synthesis, Characterization and Behavior in the Polymerization of 1,3-Butadiene. [J/OL]. Chinese Journal of Polymer Science, 2024,421-7.
Ricci, G.; Palucci, B.; Losio, S.; Sommazzi, A.; Masi, F.; Pampaloni, G.; Guelfi, M. Iminopyridine manganese and nickel complexes: synthesis, characterization and behavior in the polymerization of 1,3-butadiene. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-024-3233-2 DOI：

Giovanni Ricci, Benedetta Palucci, Simona Losio, et al. Iminopyridine Manganese and Nickel Complexes: Synthesis, Characterization and Behavior in the Polymerization of 1,3-Butadiene. [J/OL]. Chinese Journal of Polymer Science, 2024,421-7. DOI： 10.1007/s10118-024-3233-2.

摘要

Abstract

Some novel manganese and nickel complexes were synthesized by reacting manganese(II) dichloride and nickel(II) dichloride with pyridyl-imine ligands differing in the nature of the substituents at the imino nitrogen atom. All the complexes were characterized by analytical and infrared data: for some of them single crystals were obtained

and their molecular structure was determined by X-ray diffraction. The complexes were used in association with methylaluminoxane (MAO) for the polymerization of 1

3-butadiene obtaining active and selective catalysts giving predominantly 1

2 polybutadiene in case of manganese catalysts and exclusively

cis

-1

4 polybutadiene in case of nickel catalysts.

关键词

Keywords

ManganeseNickelCatalystsPolymerizationPolybutadieneX-ray structures

references

Porri, L.; A. Giarrusso, A. “Conjugated Diene Polymerization” inComprehensive Polymer Science, (Eds.: G. Eastmond, A. Edwith, S. Russo, P. Sigwalt) Pergamon Press Ltd., Oxford, 1989, p. 53..

Ricci, G.; Sommazzi, A.; Masi, F.; Ricci, M.; Boglia, A.; Leone, G. Well-defined transition metal complexes with phosphorus and nitrogen ligands for 1,3-dienes polymerization.Coord. Chem. Rev.2010,254, 661−676..

Ricci, G.; Pampaloni, G.; Sommazzi, A.; Masi, F. Dienes polymerization: where we are and what lies ahead.Macromolecules2021,54, 5879−5914..

Porri, L.; Giarrusso, A.; Ricci, G. Recent views on the mechanism of diolefin polymerization with transition metal initiator systems.Prog. Polym. Sci.1991,16, 405−441..

Raynaud, J.; Wu, J.Y.; Ritter, T. Iron-catalyzed polymerization of isoprene and other 1,3-dienes.Angew. Chem.2012,51, 11805−11808..

Guo, L.; Jing, X.; Xiong, S.; Liu, Y.; Liu, Z.; Chen, C. Influences of Alkyl and Aryl Substituents on Iminopyridine Fe(II)- and Co(II)-Catalyzed Isoprene Polymerization.Polymers2016,8, 389..

Hashmi, O. H.; Champouret, Y.; Visseaux, M. Highly active iminopyridyl iron-based catalysts for the polymerization of isoprene.Molecules2019,24, 3024..

Champouret, Y.; Hashmi, O. H.; Visseaux, M. Discrete iron-based complexes: Applications in homogeneous coordination-insertion polymerization catalysis.Coord. Chem. Rev.2019,390, 127−170..

Ricci, G.; Leone, G.; Zanchin, G.; Palucci, B.; Boccia, A. C.; Sommazzi, A.; Masi, F.; Zacchini, S.; Guelfi, M.; Pampaloni, G. Highly stereoregular 1,3-butadiene and isoprene polymers through monoalkyl-N-aryl-substituted iminopyridine iron complex-based catalysts: synthesis and characterization.Macromolecules2021,54, 9947−9959..

Zhao, M.; Wang, L.; Mahmood, Q.; Jing, C.; Zhu, G.; Zhang, X.; Wang, X.; Wang, Q. Controlled isoprene polymerization mediated by iminopyridine-iron(II) acetylacetonate pre-catalysts.Appl. Organomet. Chem.2019,33, e4836..

Scoti, M.; De Stefano, F.; Zanchin, G.; Leone, G.; De Rosa, C.; Ricci, G. Synthesis, structure, and properties of poly(isoprene)s of different constitutions and configurations from catalysts based on complexes of Nd, Co, and Fe.Macromolecules2023,56, 4629−4638..

Ricci, G.; Boccia, A.C.; Palucci, B.; Sommazzi, A.; Masi, F.; Scoti, M.; De Stefano, F.; De Rosa, C. Synthesis of stereoregular polymyrcenes using neodymium-, iron- and copper-based catalysts.Polym. Chem.2024,15, 1367−1376..

Ricci, G.; Leone, G.; Zanchin, G.; Masi, F.; Guelfi, M.; Pampaloni, G. Dichloro(2,2′-bipyridine)copper/MAO: an active and stereospecific catalyst for 1,3-diene polymerization.Molecules2023,28, 374..

Ricci, G.; Leone, G.; Zanchin, G.; Masi, F.; Zacchini, S.; Bresciani, G.; Guelfi, M.; Pampaloni, G. Iminopyridine copper complex-based catalysts for 1,3-dienes stereospecific polymerization.Macromol. Chem. Phys.2023,224, 2300037..

Boor jr, J. Ziegler polymerization of olefins. X. Transition metal salts having four and more d-electrons.J. Polym. Sci., Part A: Polym. Chem.1971,9, 3075..

Campora, J.; Ortiz de la Tabla, L.; Palma, P.; Alvarez, E.; Lahoz, F.; Mereiter, K. Synthesis and catalytic activity of cationic allyl complexes of nickel stabilized by a single N-heterocyclic carbene ligand.Organometallics2006,25, 3314−3316..

Kim, J. S.; Chadran, D.; Park, D. W.; Ha, C. S.; Kim, I. Polymerization of 1,3-butadiene with nickel(II)α-diimine complexes combined with ethylaluminum sesquichloride.Stud. Surf. Sci. Catal.2007,172, 525−526..

O’Connor, A. R.; White, P. S.; Brookhart, M. The mechanism of polymerization of butadiene by “ligand-free” nickel(II) Complexes.J. Am. Chem. Soc.2007,129, 4142−4143..

Kim, J. S.; Chandran, D.; Park, D. W.; Ha, C. S.; Kim, I. Polymerization of 1,3-butadiene with nickel(II)α-diimine complexes combined with ethylaluminum sesquichloride.Sci. Technol. Catal. 2006 , 525-526..

O’Connor, A. R.; Brookhart, M. Polymerization of 1,3-dienes and styrene catalyzed by cationic allyl Ni(II) complexes.J. Polym. Sci., Part A: Polym. Chem.2010,48, 1901−1912..

Singh, A.; Chavda, A.; Nandula, S.; Vir Jasra, R.; Maiti, M. Kinetic study on stereospecific polymerization of 1,3-butadiene using a nickel based catalyst system in environmentally friendly solvent.Ind. Eng. Chem. Res.2012,51, 11066−11071..

Wang, B.; Gong, D.; Wu, G.; Zhang, X. Polymerization of 1,3-butadiene using (salen)Ni(II) and (salphen)Ni(II) complexes in combination with methyl- aluminoxane.e-Polymers 2012 , 066..

Ai, P.; Chen, L.; Guo, Y.; Jie, S.; Li, B. G. Polymerization of 1,3-butadiene catalyzed by cobalt(II) and nickel(II) complexes bearing imino- or amino-pyridyl alcohol ligands in combination with ethylaluminum sesquichloride.J. Organomet. Chem.2012,705, 51−58..

Zhang, J.; Gao, W.; Lang, X.; Wu, Q.; Zhang, L.; Mu, Y. Ni(II) and Fe(II) complexes based on bis(imino)aryl pincer ligands: synthesis, structural characterization and catalytic activities.Dalton Trans.2012,41, 9639−9645..

Nobbs, J. D.; Tomov, A. K.; Cariou, R.; Gibson, V. C.; White, A. J. P.; Britovsek, G. J. P. Thio-Pybox and Thio-Phebox complexes of chromium, iron, cobalt and nickel and their application in ethylene and butadiene polymerisation catalysis.Dalton Trans.2012,41, 5949−5964..

Vaultier, F.; Monteil, V.; Spitz, R.; Thuilliez, J.; Boisson, C. New insights on Ni-based catalysts for stereospecific polymerization of butadiene.Polym. Chem.2012,3, 1490−1494..

Liu, H.; Wang, F.; Jia, X. Y.; Liu, L.; Bi, J. F.; Zhang, C. Y.; Zhao, L. P.; Bai, C. X.; Hu, Y. M.; Zhang, X. Q. Synthesis, characterization, and 1,3-butadiene polymerization studies of Co(II), Ni(II), and Fe(II) complexes bearing 2-(N-arylcarboximidoylchloride)quinoline ligand.J. Mol. Catal. A: Chem.2014,391, 25−35..

Liu, H.; Wang, F.; Han, C.; Zhang, H.; Bai, C.; Hu, Y.; Zhang, X. Cobalt and nickel complexes supported by 2,6-bis(imidate)pyridyl ligands: synthesis, characterization, and 1,3-butadiene polymerization studies.Inorg. Chim. Acta2015,434, 135−142..

Liu, L.; Wang, F.; Zhang, C.; Liu, H.; Wu, G.; Zhang, X. Thermally robust α-diimine nickel and cobalt complexes forcis-1,4 selective 1,3-butadiene polymerizations.Molecular Catalysis2022,517, 112044..

Bruker, APEX4 V2021.10-0, Bruker AXS Inc., Madison, Wisconsin, USA, 2021 .

Bruker, SAINT v8.30A, Bruker AXS Inc., Madison, Wisconsin, USA, 2012 .

Bruker, XPREP V2014/2, Bruker AXS Inc., Madison, Wisconsin, USA, 2014 .

Bruker, SADABS V2016/2, Bruker AXS Inc., Madison, Wisconsin, USA, 2016 .

G.M. Sheldrick, SHELXL-2019/1, Bruker AXS Inc., Madison, Wisconsin, USA, 2019 .

Mochel, V. D. C-13 NMR of polybutadiene.J. Polym. Sci., Part A: Polym. Chem.1972,10, 1009−1018..

Elgert, K. F.; Quack, G.; Stutzel, B. Zur struktur des polybutadiens, 2†. Das 13C-NMR-Spektrum des 1,2-polybutadiens.Makromol. Chem.1974,175, 1955−1960..

Xu, M.; Wang, Y.; Zhou, Y.; Yao, Z. J.N,N-Chelate nickel(II) complexes bearing Schiff base ligands as efficient hydrogenation catalysts for amine synthesis.J. Organomet. Chem. 2022 ,959, 122187..

Tsaulwayo, N.; Kumah, R. T.; Ojwach, S. O. Applications of imino-pyridine Ni(II) complexes as catalysts in the transfer hydrogenation of ketones.J. Mol. Struct.2021,1232, 129987..

Laine, T. V.; Klinga, M.; Leskelä, M. Synthesis and X-ray structures of new mononuclear and dinuclear diimine complexes of late transition metals.Eur. J. Inorg. Chem.1999,6, 959−964..

Sood, A.; Räisänen, M.; Aitola, E.; Sibaouih, A.; Colacia, E.; Ahlgren, M.; Nieger, M.; Repo, T.; Leskelä, M. Synthesis and crystal structure determination of Mn(II) Schiff base complexes and their performance in ethene polymerization.Polyhedron2013,56, 221−229..

Ban, H.T.; Kase, T.; Murata, M. Manganese-based transition metal complexes as new catalysts for olefin polymerizations.J. Polym. Sci., Part A: Polym. Chem.2001,29, 3733−3738..

Schulz, M.; Klopfleisch, M.; Görls, H.; Kahnes, M.; Westerhausen, M. Synthesis and structural diversity of 2-pyridylmethylideneamine complexes of zinc(II) chloride.Inorg. Chim. Acta2009,362, 4706−4712..

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Nickel(II) α-Diimine Catalysts with Carboxyl Groups for Ethylene Oligomerization and Polymerization

HALONICKEL 2,4-DI-t-BUTYL-6-(QUINOLIN-8-YLIMINOMETHYL)PHENOLATES: SYNTHESIS, CHARACTERIZATION AND ETHYLENE REACTIVITY

High Performance Microwave Absorption Material Based on Metal-Backboned Polymer

Regio- and Stereoselective Polymerization of Bio-based Ocimene by Rare-Earth Metal Catalysts

Access to High-Molecular-Weight Polyethylenes through High Temperature Ethylene Polymerization Catalysed by Ethylene-Bridged ansa-(3-R-Cyclopentadienyl)(Fluorenyl) Zirconocene Complexes

Related Author

Bing Liu

Meng-zhe Fang

Su-Yun Jie

Zhi-yang Bu

Bo-Geng Li

Qi-song Shi

Xiang Hao

Carl Redshaw

Related Institution

State Key Laboratory of Chemical Engineering, College of Chemical and Biological Engineering, Zhejiang University

Department of Chemistry, University of Hull, Hull

Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences

College of Materials Science and Engineering, Beijing Institute of Petrochemical Technology

Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, and Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University

⁰