Overview of cobalt-mediated radical polymerization: Roots, state of the art and future prospects

Progress in Polymer Science (Oxford)

Volumn 34, Issue 3, 2009, Pages 211-239

  Debuigne, Antoine ^a   Poli, Rinaldo ^b,c   Jérôme, Christine ^a   Jérôme, Robert ^a   Detrembleur, Christophe ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^c INSTITUT UNIVERSITAIRE DE FRANCE   (France)

Author keywords

Cobalt mediated radical polymerization; Controlled radical polymerization; Copolymers; Macromolecular engineering

Indexed keywords

ACRYLIC MONOMERS; ATOM TRANSFER RADICAL POLYMERIZATION; CHEMICAL BONDS; CHEMICAL REACTIONS; COBALT; COPOLYMERIZATION; COPOLYMERS; ESTERS; MACROMOLECULES; POLYMERS;

COBALT-CARBON BONDS; COMPUTATIONAL CHEMISTRIES; CONTROLLED RADICAL POLYMERIZATION; DEGENERATIVE CHAIN TRANSFERS; FUTURE PROSPECTS; MACROMOLECULAR ENGINEERING; POLYMER CHAINS; STATE-OF-THE ARTS; VINYL ESTER MONOMERS;

FREE RADICAL POLYMERIZATION;

EID: 60949084913     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2008.11.003     Document Type: Review

References (143)

1. Braunecker W.A., and Matyjaszewski K. Controlled/living radical polymerization: features, developments, and perspectives. Prog Polym Sci 32 (2007) 93-146
2. Georges M.K., Veregin R.P.N., Kazmaier P.M., and Hamer G.K. Narrow molecular weight resins by a free-radical polymerization process. Macromolecules 26 (1993) 2987-2988
3. Hawker C.J., Bosman A.W., and Harth E. New polymer synthesis by nitroxide mediated living radical polymerizations. Chem Rev 101 (2001) 3661-3688
4. Solomon D.H. Genesis of the csiro polymer group and the discovery and significance of nitroxide-mediated living radical polymerization. J Polym Sci Part A: Polym Chem 43 (2005) 5748-5764
5. Charleux B., and Nicolas J. Water-soluble sg1-based alkoxyamines: a breakthrough in controlled/living free-radical polymerization in aqueous dispersed media. Polymer 48 (2007) 5813-5833
6. Sciannamea V., Jerome R., and Detrembleur C. In-situ nitroxide-mediated radical polymerization (nmp) processes: their understanding and optimization. Chem Rev 108 (2008) 1104-1126
7. Matyjaszewski K., and Xia J. Atom transfer radical polymerization. Chem Rev 101 (2001) 2921-2990
8. Kamigaito M., Ando T., and Sawamoto M. Metal-catalyzed living radical polymerization. Chem Rev 101 (2001) 3689-3746
9. Tsarevsky N.V., and Matyjaszewski K. Environmentally benign atom transfer radical polymerization: towards "green" processes and materials. J Polym Sci Part A: Polym Chem 44 (2006) 5098-5112
10. Tsarevsky N.V., and Matyjaszewski K. "Green" atom transfer radical polymerization: from process design to preparation of well-defined environmentally friendly polymeric materials. Chem Rev 107 (2007) 2270-2299
11. Lowe A.B., and McCormick C.L. Reversible addition-fragmentation chain transfer (raft) radical polymerization and the synthesis of water-soluble (co)polymers under homogeneous conditions in organic and aqueous media. Prog Polym Sci 32 (2007) 283-351
12. Perrier S., and Takolpuckdee P. Macromolecular design via reversible addition-fragmentation chain transfer (raft)/xanthates (madix) polymerization. J Polym Sci Part A: Polym Chem 43 (2005) 5347-5393
13. Favier A., and Charreyre M.-T. Experimental requirements for an efficient control of free-radical polymerizations via the reversible addition-fragmentation chain transfer (raft) process. Macromol Rapid Commun 27 (2006) 653-692
14. In: Barner-Kowollik C. (Ed). Handbook of RAFT polymerization (2008), Wiley VCH
15. Wayland B.B., Poszmik G., Mukerjee S.L., and Fryd M. Living radical polymerization of acrylates by organocobalt porphyrin complexes. J Am Chem Soc 116 (1994) 7943-7944
16. Arvanitopoulos L.D., Greuel M.P., and Harwood H.J. "Living" free radical polymerization using alkyl cobaloximes as photoinitiators. Polym Prep (Am Chem Soc Div Polym Chem) 35 2 (1994) 549-550
17. Debuigne A., Caille J.-R., and Jerome R. Highly efficient cobalt-mediated radical polymerization of vinyl acetate. Angew Chem Int Ed 44 (2005) 1101-1104
18. Lutz J.-F., Lacroix-Desmazes P., Boutevin B., Le Mercier C., Gigmes D., Bertin D., et al. Comparative study of a series of nitroxides and alkoxyamines in controlled/"living" radical polymerization. Polym Prepr (Am Chem Soc Div Polym Chem) 43 2 (2002) 287-288
19. Wakioka M., Baek K.-Y., Ando T., Kamigaito M., and Sawamoto M. Possibility of living radical polymerization of vinyl acetate catalyzed by iron(I) complex. Macromolecules 35 (2002) 330-333
20. Iovu M.C., and Matyjaszewski K. Controlled/living radical polymerization of vinyl acetate by degenerative transfer with alkyl iodides. Macromolecules 36 (2003) 9346-9354
21. Rizzardo E., Chiefari J., Mayadunne R.T.A., Moad G., and Thang S.H. Synthesis of defined polymers by reversible addition-fragmentation chain transfer: the raft process. In: Matyjaszewski K. (Ed). Controlled/living radical polymerization. ACS Symp Ser, vol. 768 (2000), Am Chem Soc, Washington, DC 278-296
22. Charmot D., Corpart P., Adam H., Zard S.Z., Biadatti T., and Bouhadir G. Controlled radical polymerization in dispersed media. Macromol Symp 150 (2000) 23-32
23. Stenzel M.H., Cummins L., Roberts G.E., Davis T.P., Vana P., and Barner-Kowollik C. Xanthate mediated living polymerization of vinyl acetate: a systematic variation in madix/raft agent structure. Macromol Chem Phys 204 (2003) 1160-1168
24. Stenzel M.H., Davis T.P., and Barner-Kowollik C. Poly(vinyl alcohol) star polymers prepared via madix/raft polymerization. Chem Commun (2004) 1546-1547
25. Favier A., Barner-Kowollik C., Davis T.P., and Stenzel M.H. A detailed on-line ft/nir and 1H nmr spectroscopic investigation into factors causing inhibition in xanthate-mediated vinyl acetate polymerization. Macromol Chem Phys 205 (2004) 925-936
26. Theis A., Davis T.P., Stenzel M.H., and Barner-Kowollik C. Probing the reaction kinetics of vinyl acetate free radical polymerization via living free radical polymerization (madix). Polymer 47 (2006) 999-1010
27. Simms R.W., Davis T.P., and Cunningham M.F. Xanthate-mediated living radical polymerization of vinyl acetate in miniemulsion. Macromol Rapid Commun 26 (2005) 592-596
28. Bernard J., Favier A., Zhang L., Nilasaroya A., Davis T.P., Barner-Kowollik C., et al. Poly(vinyl ester) star polymers via xanthate-mediated living radical polymerization: from poly(vinyl alcohol) to glycopolymer stars. Macromolecules 38 (2005) 5475-5484
29. Destarac M, Charmot D, Zard S, Gauthier-Gilaizeau I. Synthesis method for polymers by controlled radical polymerisation with xanthates. WO 0142312, assigned to Rhone Poulenc chimie Fr; 2001.
30. Rizzardo E., Chiefari J., Mayadunne R., Moad G., and Thang S. Tailored polymer architectures by reversible addition-fragmentation chain transfer. Macromol Symp 174 (2001) 209-212
31. Kwak Y., Goto A., Fukuda T., Kobayashi Y., and Yamago S. A systematic study on activation processes in organotellurium-mediated living radical polymerizations of styrene, methyl methacrylate, methyl acrylate, and vinyl acetate. Macromolecules 39 (2006) 4671-4679
32. Yamago S., Ray B., Iida K., Yoshida J., Tada T., Yoshizawa K., et al. Highly versatile organostibine mediators for living radical polymerization. J Am Chem Soc 126 (2004) 13908-13909
33. Poli R. Relationship between one-electron transition-metal reactivity and radical polymerization processes. Angew Chem Int Ed 45 (2006) 5058-5070
34. Schrauzer G.N., Sibert J.W., and Windgassen R.J. Photochemical and thermal cobalt-carbon bond cleavage in alkylcobalamins and related organometallic compounds. Comparative study. J Am Chem Soc 90 (1968) 6681-6688
35. Halpern J., Ng F.T.T., and Rempel G.L. Metal-alkyl bond dissociation energies in organocobalt compounds related to vitamin b12 coenzymes. J Am Chem Soc 101 (1979) 7124-7126
36. Halpern J. Determination and significance of transition metal-alkyl bond dissociation energies. Acc Chem Res 15 (1982) 238-244
37. Tsou T.T., Loots M., and Halpern J. Kinetic determination of transition metal-alkyl bond dissociation energies: application to organocobalt compounds related to B12 coenzymes. J Am Chem Soc 104 (1982) 623-624
38. Flora T.T.N., and Rempel G.L. Ligand effects on transition metal-alkyl bond dissociation energies. J Am Chem Soc 104 (1982) 621-623
39. Halpern J. Mechanisms of coenzyme b12-dependent rearrangements. Science 227 (1985) 869-875
40. Hay B.P., and Finke R.G. Thermolysis of the cobalt-carbon bond of adenosylcobalamin. 2. Products, kinetics, and cobalt-carbon bond dissociation energy in aqueous solution. J Am Chem Soc 108 (1986) 4820-4829
41. Fischer H. Unusual selectivities of radical reactions by internal suppression of fast modes. J Am Chem Soc 108 (1986) 3925-3927
42. Fischer H. The persistent radical effect: a principle for selective radical reactions and living radical polymerizations. Chem Rev 101 (2001) 3581-3610
43. Kräutler B. Acetylcobalamin from photoinduced carbonylation of methylcobalamin. Helv Chim Acta 67 (1984) 1053-1059
44. Daikh B.E., and Finke R.G. The persistent radical effect: a prototype example of extreme, 105 to 1, product selectivity in a free-radical reaction involving persistent. CoII[macrocycle] and alkyl free radicals. J Am Chem Soc 114 (1992) 2938-2943
45. Studer A. The persistent radical effect in organic synthesis. Chem Eur J 7 (2001) 1159-1164
46. Pattenden G. Cobalt-mediated radical reactions in organic synthesis. Chem Soc Rev 17 (1988) 361-382
47. Iqbal J., Bhatia B., and Nayyar N.K. Transition metal-promoted free-radical reactions in organic synthesis: the formation of carbon-carbon bonds. Chem Rev 94 (1994) 519-564
48. Ghosez A., Goebel T., and Giese B. Syntheses and reactions of glycosylcobaloximes. Chem Ber 121 (1988) 1807-1811
49. Branchaud B.P., Meier M.S., and Choi Y. Alkyl-alkenyl cross coupling via alkyl cobaloxime radical chemistry. An alkyl equivalent to the heck reaction compatible with common organic functional groups. Tetrahedron Lett 29 (1988) 167-170
50. Branchaud B.P., and Choi Y.L. Effect of a remote ligand substituent on premature b-hydrogen elimination in a cobaloxime-mediated radical alkyl-alkenyl cross coupling. Tetrahedron Lett 29 (1988) 6037-6038
51. Coveney D.J., Patel V.F., and Pattenden G. Acylcobalt salophen reagents. Precursors to acyl radical intermediates for inter- and intramolecular oxidative Michael addition reactions. Tetrahedron Lett 28 (1987) 5949-5952
52. Davis T.P., Kukulj D., Haddleton D.M., and Maloney D.R. Cobalt-mediated free-radical polymerization of acrylic monomers. Trends Polym Sci 3 (1995) 365-373
53. Gridnev A. The 25th anniversary of catalytic chain transfer. J Polym Sci Part A: Polym Chem 38 (2000) 1753-1766
54. Gridnev A.A., and Ittel S.D. Catalytic chain transfer in free-radical polymerizations. Chem Rev 101 (2001) 3611-3659
55. Melby LR, Janowicz AH, Ittel SD. Cobalt(II) chelates as chain transfer agents in free radical polymerizations. USA: EP196783, assigned to Du Pont de Nemours, E. I., and Co.; 1986.
56. Moad G, Rizzardo E, Moad CL, Ittel SD, Wilczek L, Gridnev AA. Catalytic polymerization process and the resulting polymers with terminal unsaturation. USA: WO 9731030, assigned to E. I. Du Pont de Nemours & Co.; Commonwealth Scientific & Industrial Research Organization; 1997.
57. Suddaby K.G., Sanayei R.A., Rudin A., and O'driscoll K.F. Catalytic chain transfer in polymerization of methyl methacrylate. Continuous synthesis and purification of macromer. J Appl Polym Sci 43 (1991) 1565-1575
58. Chiefari J., Jeffery J., Mayadunne R.T.A., Moad G., Rizzardo E., and Thang S.H. Chain transfer to polymer: a convenient route to macromonomers. Macromolecules 32 (1999) 7700-7702
59. Chiu T.Y.J., Heuts J.P.A., Davis T.P., Stenzel M.H., and Barner-Kowollik C. Synthesis of macromonomers via catalytic chain transfer (cct) polymerization and their characterization via nmr spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Macromol Chem Phys 205 (2004) 752-761
60. Boutevin B., David G., and Boyer C. Telechelic oligomers and macromonomers by radical techniques. Adv Polym Sci 206 (2007) 31-135
61. Cacioli P., Hawthorne D.G., Laslett R.L., Rizzardo E., and Solomon D.H. Copolymerization of w-unsaturated oligo(methyl methacrylate): new macromonomers. J Macromol Sci Part A: Pure Appl Chem 23 (1986) 839-852
62. Muratore L.M., Steinhoff K., and Davis T.P. Self-reinforcing hydrogels comprised of hydrophobic methyl methacrylate macromers copolymerized with either n-vinyl-2-pyrrolidone or 2-hydroxyethyl acrylate. J Mater Chem 9 (1999) 1687-1691
63. Greuel MP. Free radical polymerizations modified by cobalt compounds. Ph.D. dissertation. University of Akron; 1992.
64. Arvanitopoulos L.D., King B.M., Huang C.-Y., and Harwood H.J. Radical polymerizations and copolymerizations mediated by organocobalt compounds. Polym Prepr (Am Chem Soc Div Polym Chem) 38 1 (1997) 752-753
65. Arvanitopoulos L.D., Greuel M.P., King B.M., Shim A.K., and Harwood H.J. Photochemical polymerizations initiated and mediated by soluble organocobalt compounds. In: Matyjaszewski K. (Ed). Controlled radical polymerization. ACS Symp Ser, vol. 685 (1998), Am Chem Soc, Washington, DC 316-331
66. Greuel MP, Arvanitopoulos LD, Harwood HJ. Cobaloxime photoinitiators for free radical polymerization. USA: US 5468785, assigned to University of Akron; 1995.
67. Harwood HJ, Shim AK. Polymers and copolymers prepared or modified by using cobalt complexes. USA: WO 0050467, assigned to University of Akron; 2000.
68. Shim A.K., and Harwood H.J. The effect of solvent on the course of acrylate polymerizations mediated by cobaloxime and the development of novel initiating systems and novel multifunctional macromonomers. Polym Prepr (Am Chem Soc Div Polym Chem) 40 2 (1999) 132-133
69. Espenson J.H., and Mcdowell M.S. Reactions of bis(dimethylglyoximato)cobalt(II) complexes with polyhalomethane. Organometallics 1 (1982) 1514-1518
70. Kijima M., Yamashita H., and Sato T. Reactions of alkylcobaloximes with oxygen under irradiation. Oxygenative conversions of the alkyl ligand. J Organomet Chem 474 (1994) 177-182
71. Greuel M.P., and Harwood H.J. Copolymerization with catalytic chain transfer. Polym Prepr (Am Chem Soc Div Polym Chem) 32 1 (1991) 545-546
72. Enikolopyan N.S., Smirnov B.R., Ponomarev G.V., and Belgovskii I.M. Catalyzed chain transfer to monomer in free radical polymerization. J Polym Sci Polym Chem 19 (1981) 879-889
73. Wayland B.B., Mukerjee S., Poszmik G., Woska D.C., Basickes L., Gridnev aA, et al. Control of radical polymerizations by metalloradicals. In: Matyjaszewski K. (Ed). Controlled radical polymerization. ACS Symp Ser, vol. 685 (1998), Am Chem Soc, Washington, DC 305-315
74. Li Y., and Wayland B.B. Macromonomer chain growth in the radical polymerization of MMA by cobalt(II) catalyzed chain transfer. Macromol Rapid Commun 24 (2003) 307-310
75. Wayland B.B., Basickes L., Mukerjee S., Wei M., and Fryd M. Living radical polymerization of acrylates initiated and controlled by organocobalt porphyrin complexes. Macromolecules 30 (1997) 8109-8112
76. Wei M., Wayland B.B., and Fryd M. Quasi-living radical polymerization of acrylates by an organocobalt porphyrin complex at room temperature. Polym Prepr (Am Chem Soc Div Polym Chem) 38 1 (1997) 681-682
77. Lu Z., Fryd M., and Wayland B.B. New life for living radical polymerization mediated by cobalt(II) metalloradicals. Macromolecules 37 (2004) 2686-2687
78. Gridnev A.A., Ittel S.D., Fryd M., and Wayland B.B. Formation of organocobalt porphyrin complexes by reactions of cobalt(ii) porphyrins with azoisobutyronitrile and organic substrates. J Chem Soc Chem Commun (1993) 1010-1011
79. Gridnev A.A., Ittel S.D., Fryd M., and Wayland B.B. Formation of organocobalt porphyrin complexes from reactions of cobalt(ii) porphyrins and dialkylcyanomethyl radicals with organic substrates: chemical trapping of a transient cobalt porphyrin hydride. Organometallics 12 (1993) 4871-4880
80. Wayland B.B., Peng C.-H., Fu X., Lu Z., and Fryd M. Degenerative transfer and reversible termination mechanisms for living radical polymerizations mediated by cobalt porphyrins. Macromolecules 39 (2006) 8219-8222
81. Goto A., Kwak Y., Fukuda T., Yamago S., Iida K., Nakajima M., et al. Mechanism-based invention of high-speed living radical polymerization using organotellurium compounds and azo-initiators. J Am Chem Soc 125 (2003) 8720-8721
82. Asandei A.D., and Moran I.W. TiCp2Cl-catalyzed living radical polymerization of styrene initiated by oxirane radical ring opening. J Am Chem Soc 126 (2004) 15932-15933
83. Asandei A.D., Moran I.W., Saha G., and Chen Y. Titanium-mediated living radical styrene polymerizations. V. Cp2TiCl-catalyzed initiation by epoxide radical ring opening: effect of solvents and additives. J Polym Sci Part A: Polym Chem 44 (2006) 2015-2026
84. Mueller A.H.E., Yan D., Litvinenko G., Zhuang R., and Dong H. Kinetic analysis of "living" polymerization processes exhibiting slow equilibria. 2. Molecular weight distribution for degenerative transfer (direct activity exchange between active and "dormant" species) at constant monomer concentration. Macromolecules 28 (1995) 7335-7338
85. Fu X., Wayland B.B., and Fryd M. Controlled/living radical polymerization mediated by organo-cobalt complexes through a degenerative transfer/radical interchange polymerization (rip) process. Polym Prepr (Am Chem Soc Div Polym Chem) 46 2 (2005) 190
86. Lu Z., Li Y., and Wayland B.B. Cobalt porphyrin controlled living radical polymerization of acrylic acid in water. Polym Prepr (Am Chem Soc Div Polym Chem) 45 1 (2004) 1053
87. Peng C.-H., Fryd M., and Wayland B.B. Organocobalt mediated radical polymerization of acrylic acid in water. Macromolecules 40 (2007) 6814-6819
88. Li Y., and Wayland B.B. Macromonomer living character in the cobalt(II) porphyrin chain transfer catalysis for radical polymerization of methacrylic acid in water. Chem Commun (2003) 1594-1595
89. Caille J.-R., Debuigne A., and Jerome R. Quinone transfer radical polymerization (qtrp) of styrene: catalysis by different metal complexes. J Polym Sci Part A: Polym Chem 43 (2005) 2723-2733
90. Debuigne A., Caille J.-R., and Jerome R. Quinone transfer radical polymerization of styrene catalyzed by metal complexes in the presence of various o-quinones. Macromolecules 38 (2005) 6310-6315
91. Debuigne A., Caille J.-R., and Jerome R. Quinone transfer radical polymerization of styrene: synthesis of the actual initiator. J Polym Sci Part A: Polym Chem 44 (2006) 1233-1244
92. Caille J.-R., Debuigne A., and Jerome R. Controlled radical polymerization of styrene by quinone transfer radical polymerization (QTRP). Macromolecules 38 (2005) 27-32
93. Debuigne A. From quinone transfer radical polymerization (QTRP) of styrene to cobalt-mediated radical polymerization (CMRP) of vinyl acetate. Ph.D. thesis dissertation. University of Liège; 2004.
94. Maria S., Kaneyoshi H., Matyjaszewski K., and Poli R. Effect of electron donors on the radical polymerization of vinyl acetate mediated by [co(acac)2]: degenerative transfer versus reversible homolytic cleavage of an organocobalt(III) complex. Chem Eur J 13 (2007) 2480-2492
95. Kaneyoshi H., and Matyjaszewski K. Effect of ligand and n-butyl acrylate on cobalt-mediated radical polymerization of vinyl acetate. Macromolecules 38 (2005) 8163-8169
96. Walker F.A. Electron spin resonance study of coordination to the fifth and sixth positions of alpha, beta, gamma, delta-tetra(p-methoxyphenyl)porphinatocobalt(II). J Am Chem Soc 92 (1970) 4235-4244
97. Cotton F.A., and Soderberg R.H. A spectroscopic study of the polymeric nature of bis(acetyl-acetonato)cobalt(II). Inorg Chem 3 (1964) 1-5
98. Debuigne A., Detrembleur C., Bryaskova R., Caille J.-R., and Jerome R. Cobalt-mediated radical polymerization of vinyl acetate: a new tool for macromolecular engineering. In: Matyjaszewski K. (Ed). Controlled/living radical polymerization. ACS Symp Ser, vol. 944 (2006), Am Chem Soc, Washington, DC 372-386
99. Debuigne A., Champouret Y., Jerome R., Poli R., and Detrembleur C. Mechanistic insights into the cobalt-mediated radical polymerization (CMRP) of vinyl acetate with cobalt(iii) adducts as initiators. Chem Eur J 14 (2008) 4046-4059
100. Baisch U., and Poli R. Copper (I/II) and cobalt (II) coordination chemistry of relevance to controlled radical polymerization processes. Polyhedron 27 (2008) 2175-2185
101. Wayland B.B., Fu X., Peng C.-H., Lu Z., and Fryd M. Living radical polymerizations mediated by metallo-radical and organo-transition metal complexes. In: Matyjaszewski K. (Ed). Controlled/living radical polymerization. ACS Symp Ser, vol. 944 (2006), Am Chem Soc, Washington, DC 358-371
102. Peng C.-H., Scricco J., Li S., Fryd M., and Wayland B.B. Organo-cobalt mediated living radical polymerization of vinyl acetate. Macromolecules 41 (2008) 2368-2373
103. Li S., De Bruin B., Peng C.-H., Fryd M., and Wayland B.B. Exchange of organic radicals with organo-cobalt complexes formed in the living radical polymerization of vinyl acetate. J Am Chem Soc 130 (2008) 13373-13381
104. Debuigne A., Michaux C., Jérôme C., Jérôme R., Poli R., and Detrembleur C. Cobalt mediated radical polymerization of acrylonitrile: kinetics investigations and DFT calculations. Chem Eur J 14 (2008) 7623-7637
105. Bernhauer K., Mueller O., and Wagner F. New chemical and biochemical developments. The vitamin b12 field. Angew Chem Int Ed 3 (1964) 200-211
106. Schrauzer G.N., and Windgassen R.J. Alkylcobaloximes and their relation to alkylcobalamins. J Am Chem Soc 88 (1966) 3738-3743
107. Dolphin D., Halko D.J., and Jonhson E. Reversible cobalt-nitrogen alkyl and acyl group migration in cobalt porphyrins. Inorg Chem 20 (1981) 4348-4351
108. Marzilli L.G., Summers M.F., Bresciani-Pahor N., Zangrando E., Charland J.P., and Randaccio L. Rare examples of structurally characterized five-coordinate organocobalt complexes. Novel dynamic nmr evidence for synergistic enhancement of cis and trans effects in b12 models. J Am Chem Soc 107 (1985) 6880-6888
109. Dölker N., Maseras F., and Lledos A. A density functional study on the effect of the trans axial ligand of cobalamin on the homolytic cleavage of the Co-C bond. J Phys Chem B 105 (2001) 7564-7571
110. Jensen K.P., and Ryde U. The axial n-base has minor influence on Co-C bond cleavage in cobalamins. J Mol Struct Theochem 585 (2002) 239-255
111. Jensen K.P., and Ryde U. Theoretical prediction of the Co-C bond strength in cobalamins. J Phys Chem A 107 (2003) 7539-7545
112. Dölker N., Morreale A., and Maseras F. Computational study on the difference between the Co-C bond dissociation energy in methylcobalamin and adenosylcobalamin. J Biol Inorg Chem 10 (2005) 509-517
113. Jensen K.P., and Ryde U. How the Co-C bond is cleaved in coenzyme b12 enzymes: a theoretical study. J Am Chem Soc 127 (2005) 9117-9128
114. Salomon O., Reiher M., and Hess B.A. Assertion and validation of the performance of the b3lyp* functional for the first transition metal row and the g2 test set. J Chem Phys 117 (2002) 4729-4737
115. Harvey J.N., and Aschi M. Modelling spin-forbidden reactions: recombination of carbon monoxide with iron tetracarbonyl. Faraday Discuss 124 (2003) 129-143
116. Conradie J., and Ghosh A. Electronic structure of trigonal-planar transition-metal-imido complexes: spin-state energetics, spin-density profiles, and the remarkable performance of the olyp functional. J Chem Theory Comput 3 (2007) 689-702
117. Wasbotten I.H., and Ghosh A. Spin-state energetics and spin-crossover behavior of pseudotetrahedral cobalt(III)-imido complexes. The role of the tripodal supporting ligand. Inorg Chem 46 (2007) 7890-7898
118. Ng F.T.T., Rempel G.L., and Halpern J. Steric influences on cobalt-alkyl bond dissociation energies. Inorg Chim Acta 77 (1983) L165-L166
119. Harvey J.N., Aschi M., Schwarz H., and Koch W. The singlet and triplet states of phenyl cation. A hybrid approach for locating minimum energy crossing points between non-interacting potential energy surfaces. Theor Chem Acc 99 (1998) 95-99
120. Harvey J.N., Poli R., and Smith K.M. Understanding the reactivity of transition metal complexes involving multiple spin states. Coord Chem Rev 238-239 (2003) 347-361
121. Debuigne A., Caille J.-R., Detrembleur C., and Jerome R. Effective cobalt mediation of the radical polymerization of vinyl acetate in suspension. Angew Chem Int Ed 44 (2005) 3439-3442
122. Detrembleur C., Debuigne A., Bryaskova R., Charleux B., and Jerome R. Cobalt-mediated radical polymerization of vinyl acetate in miniemulsion: very fast formation of stable poly(vinyl acetate) latexes at low temperature. Macromol Rapid Commun 27 (2006) 37-41
123. Bryaskova R., Detrembleur C., Debuigne A., and Jerome R. Cobalt-mediated radical polymerization (cmrp) of vinyl acetate initiated by redox systems: toward the scale-up of CMRP. Macromolecules 39 (2006) 8263-8268
124. Debuigne A., Caille J.-R., and Jerome R. Synthesis of end-functional poly(vinyl acetate) by cobalt-mediated radical polymerization. Macromolecules 38 (2005) 5452-5458
125. Sciannamea V., Debuigne A., Piette Y., Jerome R., and Detrembleur C. Supported cobalt mediated radical polymerization (SCMRP) of vinyl acetate and recycling of the cobalt complex. Chem Commun (2006) 4180-4182
126. In: Matyjaszewski K. (Ed). Controlled radical polymerization. ACS Symp Ser, vol. 685 (1998), Am Chem Soc, Washington, DC
127. In: Matyjaszewski K. (Ed). Controlled/living radical polymerization. ACS Symp Ser, vol. 768 (2000), Am Chem Soc, Washington, DC
128. In: Matyjaszewski K. (Ed). Advances in controlled/living radical polymerization. ACS Symp Ser, vol. 854 (2002), Am Chem Soc, Washington, DC
129. In: Matyjaszewski K. (Ed). Controlled/living radical polymerization. ACS Symp Ser, vol. 944 (2006), Am Chem Soc, Washington, DC
130. McAllister R.M., and Weber J.H. Preparation and reactions of alkyl-cobalt complexes containing schiff base ligands. J Organomet Chem 77 (1974) 91-105
131. Dodd D., and Johnson M.D. Organic compounds of cobalt(III). J Organomet Chem 52 (1973) 1-232
132. Kemmitt R.D.W., and Russell D.R. In: Wilkinson G., Stone F.G.A., and Abel E.W. (Eds). Comprehensive organometallic chemistry vol. 5 (1982), Pergamon Press, Oxford 1-276
133. Debuigne A., Caille J.-R., Willet N., and Jerome R. Synthesis of poly(vinyl acetate) and poly(vinyl alcohol) containing block copolymers by combination of cobalt-mediated radical polymerization and ATRP. Macromolecules 38 (2005) 9488-9496
134. Ciriano M.V., Korth H.-G., Van Scheppingen W.B., and Mulder P. Thermal stability of 2,2,6,6-tetramethylpiperidine-1-oxyl (tempo) and related n-alkoxyamines. J Am Chem Soc 121 (1999) 6375-6381
135. Detrembleur C., Stoilova O., Bryaskova R., Debuigne A., Mouithys-Mickalad A., and Jerome R. Preparation of well-defined pvoh/c60 nanohybrids by cobalt-mediated radical polymerization of vinyl acetate. Macromol Rapid Commun 27 (2006) 498-504
136. Hurtgen M. Synthesis of poly(vinyl alcohol) and poly(n-vinyl pyrrolidone) containing nanohybrids c60 as photodynamic cancer therapy agents. Masters dissertation. University of Liège; 2007.
137. Kaneyoshi H., and Matyjaszewski K. Radical (co)polymerization of vinyl chloroacetate and n-vinylpyrrolidone mediated by bis(acetylacetonate)cobalt derivatives. Macromolecules 39 (2006) 2757-2763
138. Kaneyoshi H., and Matyjaszewski K. Synthesis of poly(vinyl acetate)-graft-polystyrene by a combination of cobalt-mediated radical polymerization and atom transfer radical polymerization. J Polym Sci Part A: Polym Chem 45 (2007) 447-459
139. Bryaskova R., Willet N., Debuigne A., Jerome R., and Detrembleur C. Synthesis of poly(vinyl acetate)-b-polystyrene and poly(vinyl alcohol)-b-polystyrene copolymers by cobalt-mediated radical polymerization. J Polym Sci Part A: Polym Chem 45 (2007) 81-89
140. Bryaskova R., Willet N., Degee P., Dubois P., Jerome R., and Detrembleur C. Copolymerization of vinyl acetate with 1-octene and ethylene by cobalt-mediated radical polymerization. J Polym Sci Part A: Polym Chem 45 (2007) 2532-2542
141. Debuigne A., Willet N., Jerome R., and Detrembleur C. Amphiphilic poly(vinyl acetate)-b-poly(n-vinylpyrrolidone) and novel double hydrophilic poly(vinyl alcohol)-b-poly(n-vinylpyrrolidone) block copolymers prepared by cobalt-mediated radical polymerization. Macromolecules 40 (2007) 7111-7118
142. Debuigne A., Warnant J., Jerome R., Voets I., De Keizer A., Cohen Stuart M.A., et al. Synthesis of novel well-defined poly(vinyl acetate)-b-poly(acrylonitrile) and derivatized water-soluble poly(vinyl alcohol)-b-poly(acrylic acid) block copolymers by cobalt-mediated radical polymerization. Macromolecules 41 (2008) 2353-2360
143. Warnant J. Preparation of poly(vinyl acetate)-b-poly(acrylonitrile) block copolymers by controlled radical polymerization. Master dissertation. University of Liège; 2007.