On the Use of Cob(II)alamin as a Spin Trap in Radical Polymerization

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

Macromolecular Research, Vol.20, No.5, 473-476, May, 2012

DOI10.1007/s13233-012-0039-9 Export Citation

On the Use of Cob(II)alamin as a Spin Trap in Radical Polymerization

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

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Hydroxocobalamin reduced with ascorbic acid acts as a spin trap for free radical polymerization in water. The reaction mechanism is dependent on monomer type. An acrylic olefin such as 2-hydroxyethyl acrylate (HEA) is polymerized at pH 7 and in the presence of a conventional radical source mainly through reversible deactivation by a coupling mechanism. In contrast, a methacrylate like polyethylene glycol methacrylate undergoes catalytic chain transfer oligomerization.

Keywords:radical polymerization;cobalamin;bioorganometallics;sustainable chemistry.

[References]

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[1] Stubbe J, Science, 266(5191), 1663 (1994)

[2] Alefounder PR, Hart GJ, Miller AD, Beifuss U, Abell C, Leeper FJ, Battersby AR, Bioorg. Chem., 17, 121 (1989)

[3] Rossi M, Glusker JP, Randaccio L, Summers MF, Toscano PJ, Marzilli LG, J. Am. Chem. Soc., 107, 1729 (1985)

[4] Randaccio L, Furlan M, Geremia S, Slouf M, Srnova I, Toffoli D, Inorg. Chem., 39(15), 3403 (2000)

[5] Brown KL, Chem. Rev., 105(6), 2075 (2005)

[6] Okada Y, Oono Y, Kenkyu Hokoku-Himeji Kogyo Daigaku., 38A, 89 (1985)

[7] Ng YH, di Lena F, Chai CLL, Polym. Chem., 2, 589 (2011)

[8] Ng YH, di Lena F, Chai CLL, Chem. Commun., 47, 6464 (2011)

[9] Nazhat NB, Golding BT, Johnson GRA, Jones P, J. Inorg. Biochem., 36, 75 (1989)

[10] Poli R, Angew. Chem. Int. Ed., 45, 5058 (2006)

[11] Debuigne A, Poli R, Jerome C, Jerome R, Detrembleur C, Prog. Polym. Sci., 34, 211 (2009)

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

[13] Hamza MSA, Zou X, Brown KL, van Eldik R, Eur. J. Inorg. Chem., 268 (2003)

[14] Kine BB, Novak RW, in Kirk-Othmer Encyclopedia of Chemical Technology, Kroschwitz JI, Howe-Grant M, Eds., John Wiley & Sons Inc., New York, 1, 369 (2007)

[15] Lutz JF, Weichenhan K, Akdemir O, Hoth A, Macromolecules, 40(7), 2503 (2007)

[16] Ahmad NM, Charleux B, Farcet C, Ferguson CJ, Gaynor SG, Hawkett BS, Heatley F, Klumperman B, Konkolewicz D, Lovell PA, Matyjaszewski K, Venkatesh R, Macromol. Rapid Commun., 30(23), 2002 (2009)

[17] Maria S, Kaneyoshi H, Matyjaszewski K, Poli R, Chem.Eur. J., 13, 2480 (2007)

[18] Gridnev AA, Ittel SD, Chem. Rev., 101(12), 3611 (2001)