Atom Transfer Radical Polymerization (ATRP) of Methyl Methacrylate Mediated by Iron(II) Chloride in the Presence of Polyethers as Both Solvents and Ligands

Yeap-Hung Ng; Fabio di Lena; Christina L. L. Chai

Macromolecular Research, Vol.20, No.6, 552-558, June, 2012

DOI10.1007/s13233-012-0077-3 Export Citation

Atom Transfer Radical Polymerization (ATRP) of Methyl Methacrylate Mediated by Iron(II) Chloride in the Presence of Polyethers as Both Solvents and Ligands

Yeap-Hung Ng¹, Fabio di Lena^{1, †}, and Christina L. L. Chai^{2, 3}

¹Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 1 Pesek Road, Jurong Island, 627833, Singapore, Korea
²Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, Chemistry@Neuros, 8 Biomedical Grove, Neuros #07-01, 138665, Singapore, Singapore, Korea
³Department of Pharmacy, National University of Singapore, 18 Science Drive 4, 117543, Singapore, Singapore

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Iron(II) chloride in combination with various polyethers form the homogeneous, “green” catalytic mixtures that are capable of promoting the well-controlled atom transfer radical polymerization of methyl methacrylate in the absence of any additional ligands or solvents. With poly(ethylene glycol)s, linear semilogarithmic plots of conversion vs. time and of molecular weight vs.monomer conversion were obtained with polydispersities as low as 1.32. The effects of the polyether structure, molecular weight, and chain-end functionality on the polymerization kinetics were also investigated.

Keywords:atom transfer radical polymerization;iron;ligand-free catalysis;poly(ethylene glycol).

[References]

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[2] Matyjaszewski K, Ed., Controlled/Living Radical Polymerization: Progress in RAFT, DT, NMP & OMRP, ACS Symp.Ser., Washington DC, 1024 (2009)

[3] Braunecker WA, Matyjaszewski K, Prog. Polym. Sci., 32, 93 (2007)

[4] Matyjaszewski K, Dong HC, Jakubowski W, Pietrasik J, Kusumo A, Langmuir, 23(8), 4528 (2007)

[5] Matyjaszewski K, Xia JH, Chem. Rev., 101(9), 2921 (2001)

[6] Kamigaito M, Ando T, Sawamoto M, Chem. Rev., 101(12), 3689 (2001)

[7] Matyjaszewski K, Tsarevsky NV, Nat. Chem., 1, 276 (2009)

[8] Ouchi M, Terashima T, Sawamoto M, Chem. Rev., 109(11), 4963 (2009)

[9] di Lena F, Matyjaszewski K, Prog. Polym. Sci., 35, 959 (2010)

[10] Ando T, Kamigaito M, Sawamoto M, Macromolecules, 30(16), 4507 (1997)

[11] Matyjaszewski K, Wei ML, Xia JH, McDermott NE, Macromolecules, 30(26), 8161 (1997)

[12] Xue ZG, Lee BW, Noh SK, Lyoo WS, Polymer, 48(16), 4704 (2007)

[13] Uchiike C, Ouchi M, Ando T, Kamigaito M, Sawamoto M, J. Polym. Sci. A: Polym. Chem., 46(20), 6819 (2008)

[14] Gibson VC, O’Reilly RK, Reed W, Wass DF, White AJP, Williams DJ, Chem. Commun., 1850 (2002)

[15] Zhang HQ, Schubert US, J. Polym. Sci. A: Polym. Chem., 42(19), 4882 (2004)

[16] Louie J, Grubbs RH, Chem. Commun., 1479 (2000)

[17] Kawamura M, Sunada Y, Kai H, Koike N, Hamada A, Hayakawa H, Jin RH, Nagashima H, Adv. Synth. Catal., 351, 2086 (2009)

[18] O'Reilly RK, Gibson VC, White AJP, Williams DJ, J. Am. Chem. Soc., 125(28), 8450 (2003)

[19] Ishio M, Katsube M, Ouchi M, Sawamoto M, Inoue Y, Macromolecules, 42(1), 188 (2009)

[20] Pearson RG, J. Am. Chem. Soc., 85, 3533 (1963)

[21] Gritzner G, Linert W, Gutmann V, J. Inorg. Nucl. Chem., 43, 1193 (1981)

[22] Linert W, Gutmann V, Baumgartner O, Wiesinger G, Kirchmayr H, Inorg. Chim. Acta., 74, 123 (1983)

[23] Wang Y, Matyjaszewski K, Macromolecules, 43(9), 4003 (2010)

[24] Chen J, Spear SK, Huddleston JG, Rogers RD, Green Chem., 7, 64 (2005)

[25] Rogers RD, Jezl ML, Bauer CB, Inorg. Chem., 33(25), 5682 (1994)

[26] Rogers RD, Zhang JH, Bauer CB, J. Alloys Compd., Refs. therein., 249, 41 (1997)

[27] Neumann R, Sasson Y, Tetrahedron,, 39, 3437 (1983)

[28] Chen XP, Qiu KY, Macromolecules, 32(26), 8711 (1999)

[29] Toke L, Sazbo GT, Acta Chim. Acad. Sci. Hung., 93, 421 (1977)

[30] Toke L, Sazbo GT, Somogyi-Werner K, Acta Chim. Acad. Sci. Hung., 101, 47 (1979)

[31] Sazbo GT, Aranyosi K, Toke L, Acta Chim. Acad. Sci. Hung., 110, 421 (1982)

[32] di Lena F, Matyjaszewski K, Chem. Commun., 6306 (2008)

[33] Tang W, Kwak Y, Braunecker W, Tsarevsky NV, Coote ML, Matyjaszewski K, J. Am. Chem. Soc., 130(32), 10702 (2008)

[34] di Lena F, Chai CLL, Polym. Chem., 1, 922 (2010)

[35] Matyjaszewski K, in Handbook of Radical Polymerization, Matyjaszewski K, Davis TP, Eds., Wiley-Interscience, New York, 361 (2002)

[36] Matyjaszewski K, Jakubowski W, Min K, Tang W, Huang J, Braunecker WA, Proc. Natl. Acad. Sci. USA., 103, 15309 (2006)