Electron transfer reactions relevant to atom transfer radical polymerization

Journal of Organometallic Chemistry

Volumn 692, Issue 15, 2007, Pages 3212-3222

  Tsarevsky, Nicolay V ^a   Braunecker, Wade A ^a   Matyjaszewski, Krzysztof ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

Atom transfer radical polymerization; Disproportionation; Electron transfer; Radical coordination

Indexed keywords

CATALYST ACTIVITY; ELECTRON TRANSPORT PROPERTIES; FREE RADICALS; POSITIVE IONS; REACTION KINETICS; REDUCTION;

CARBOCATIONS; ELECTRON TRANSFER REACTIONS; RADICAL COORDINATION;

ATOM TRANSFER RADICAL POLYMERIZATION;

EID: 34250197563     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.01.051     Document Type: Article

References (157)

1. Wang J.-S., and Matyjaszewski K.J. Am. Chem. Soc. 117 (1995) 5614
2. Kato M., Kamigaito M., Sawamoto M., and Higashimura T. Macromolecules 28 (1995) 1721
3. Matyjaszewski K., and Xia J. J. Chem. Rev. 101 (2001) 2921
4. Kamigaito M., Ando T., and Sawamoto M. Chem. Rev. 101 (2001) 3689
5. Matyjaszewski K., and Spanswick J. Mat. Today 8 3 (2005) 26
6. Patten T.E., and Matyjaszewski L. Acc. Chem. Res. 32 (1999) 895-903
7. Coessens V., Pintauer T., and Matyjaszewski K. Prog. Polym. Sci. 26 (2001) 337
8. Davis K.A., and Matyjaszewski K. Adv. Polym. Sci. 159 (2002) 1
9. Matyjaszewski K. Prog. Polym. Sci. 30 (2005) 858
10. In: Matyjaszewski K. (Ed). Controlled/Living Radical Polymerization. From Synthesis to Materials (ACS Symp. Ser. 944); (2006), ACS, Washington, DC
11. Braunecker W.A., and Matyjaszewski K.J. Mol. Catal. A: Chem. 254 (2006) 155
12. Braunecker W.A., and Matyjaszewski K. Prog. Polym. Sci. 32 (2007) 93
13. In: Matyjaszewski K., and Davis T.P. (Eds). Handbook of Radical Polymerization; (2002), Wiley, Hoboken
14. Qiu J., Matyjaszewski K., Thouin L., and Amatore C. Macromol. Chem. Phys. 201 (2000) 1625
15. Matyjaszewski K., Goebelt B., Paik H.-j., and Horwitz C.P. Macromolecules 34 (2001) 430
16. Tang H., Arulsamy N., Sun J., Radosz M., Shen Y., Tsarevsky N.V., Braunecker W.A., Tang W., and Matyjaszewski K.J. Am. Chem. Soc. 128 (2006) 16277
17. Tsarevsky N.V., Braunecker W.A., Tang W., Brooks S.J., Matyjaszewski K., Weisman G.R., and Wong E.H.J. Mol. Catal. A: Chem. 257 (2006) 132
18. Kabachii Y.A., Kochev S.Y., Bronstein L.M., Blagodatskikh I.B., and Valetsky P.M. Polym. Bull. 50 (2003) 271
19. Brandts J.A.M., van de Geijn P., van Faassen E.E., Boersma J., and Van Koten G.J. Organomet. Chem. 584 (1999) 246
20. Le Grognec E., Claverie J., and Poli R.J. Am. Chem. Soc. 123 (2001) 9513
21. Stoffelbach F., Claverie J., and Poli R. Compt. Rend. Chim. 5 (2002) 37
22. Stoffelbach F., Haddleton D.M., and Poli R. Eur. Polym. J. 39 (2003) 2099
23. Kotani Y., Kamigaito M., and Sawamoto M. Macromolecules 32 (1999) 2420
24. Kotani Y., Kamigaito M., and Sawamoto M. Macromolecules 33 (2000) 6746
25. Uegaki H., Kotani Y., Kamigaito M., and Sawamoto M. ACS Symp. Ser. 760 (2000) 196
26. Percec V., Barboiu B., Neumann A., Ronda J.C., and Zhao M. Macromolecules 29 (1996) 3665
27. Ando T., Kamigaito M., and Sawamoto M. Tetrahedron 53 (1997) 15445
28. Simal F., Demonceau A., and Noels A.F. Angew. Chem., Int. Ed. 38 (1999) 538
29. Simal F., Sebille S., Hallet L., Demonceau A., and Noels A.F. Macromol. Symp. 161 (2000) 73
30. De Clercq B., and Verpoort F. Tetrahedron Lett. 43 (2002) 4687
31. Opstal T., and Verpoort F. Angew. Chem., Int. Ed. 42 (2003) 2876
32. Haas M., Solari E., Nguyen Q.T., Gautier S., Scopelliti R., and Severin K. Adv. Synth. Catal. 348 (2006) 439
33. Ando T., Kamigaito M., and Sawamoto M. Macromolecules 30 (1997) 4507
34. Matyjaszewski K., Wei M., Xia J., and McDermott N.E. Macromolecules 30 (1997) 8161
35. Moineau G., Dubois P., Jerome R., Senninger T., and Teyssie P. Macromolecules 31 (1998) 545
36. Xia J., Paik H.-j., and Matyjaszewski K. Macromolecules 32 (1999) 8310
37. Teodorescu M., Gaynor S.G., and Matyjaszewski K. Macromolecules 33 (2000) 2335
38. Zhu S., and Yan D. Macromolecules 33 (2000) 8233
39. Zhu S., Yan D., Zhang G., and Li M. Macromol. Chem. Phys. 201 (2000) 2666
40. Gibson V.C., O'Reilly R.K., Reed W., Wass D.F., White A.J.P., and Williams D.J. Chem. Commun. (2002) 1850
41. Gibson V.C., O'Reilly R.K., Wass D.F., White A.J.P., and Williams D.J. Macromolecules 36 (2003) 2591
42. Moineau G., Granel C., Dubois P., Jerome R., and Teyssie P. Macromolecules 31 (1998) 542
43. Mecerreyes D., Moineau G., Dubois P., Jerome R., Hedrick J.L., Hawker C.J., Malmstrom E.E., and Trollsas M. Angew. Chem., Int. Ed. 37 (1998) 1274
44. Opstal T., Zednik J., Sedlacek J., Svoboda J., Vohlidal J., and Verpoort F. Coll. Czech. Chem. Commun. 67 (2002) 1858
45. Vohlidal J., Pacovska M., Sedlacek J., Svoboda J., Zednik J., and Balcar H. NATO Sci. Ser., II: Math., Phys. Chem. 122 (2003) 131
46. Granel C., Dubois P., Jerome R., and Teyssie P. Macromolecules 29 (1996) 8576
47. Uegaki H., Kotani Y., Kamigaito M., and Sawamoto M. Macromolecules 30 (1997) 2249
48. Uegaki H., Kotani Y., Kamigaito M., and Sawamoto M. Macromolecules 31 (1998) 6756
49. Carrot G., Hilborn J., Hedrick J.L., and Trollsas M. Macromolecules 32 (1999) 5171
50. Husseman M., Malmstrom E.E., McNamara M., Mate M., Mecerreyes D., Benoit D.G., Hedrick J.L., Mansky P., Huang E., Russell T.P., and Hawker C.J. Macromolecules 32 (1999) 1424
51. Moineau G., Minet M., Dubois P., Teyssie P., Senninger T., and Jerome R. Macromolecules 32 (1999) 27
52. Moineau C., Minet M., Teyssie P., and Jerome R. Macromolecules 32 (1999) 8277
53. Uegaki H., Kamigaito M., and Sawamoto M.J. Polym. Sci.: Part A: Polym. Chem. 37 (1999) 3003
54. Lecomte P., Drapier I., Dubois P., Teyssie P., and Jerome R. Macromolecules 30 (1997) 7631
55. Wang B., Zhuang Y., Luo X., Xu S., and Zhou X. Macromolecules 36 (2003) 9684
56. Braunecker W.A., Itami Y., and Matyjaszewski K. Macromolecules 38 (2005) 9402
57. Wang J.S., and Matyjaszewski K. Macromolecules 28 (1995) 7901
58. Xia J., and Matyjaszewski K. Macromolecules 30 (1997) 7697
59. Haddleton D.M., Jasieczek C.B., Hannon M.J., and Shooter A.J. Macromolecules 30 (1997) 2190
60. Matyjaszewski K. Macromolecules 31 (1998) 4710
61. Haddleton D.M., Crossman M.C., Dana B.H., Duncalf D.J., Heming A.M., Kukulj D., and Shooter A.J. Macromolecules 32 (1999) 2110
62. Xia J., and Matyjaszewski K. Macromolecules 32 (1999) 2434
63. Teodorescu M., and Matyjaszewski K. Macromolecules 32 (1999) 4826
64. Xia J., Gaynor S.G., and Matyjaszewski K. Macromolecules 31 (1998) 5958
65. Xia J., Zhang X., and Matyjaszewski K. ACS Symp. Ser. 760 (2000) 207
66. Queffelec J., Gaynor S.G., and Matyjaszewski K. Macromolecules 33 (2000) 8629
67. Inoue Y., and Matyjaszewski K. Macromolecules 36 (2003) 7432
68. Ding S., Shen Y., and Radosz M.J. Polym. Sci.: Part A: Polym. Chem. 42 (2004) 3553
69. Pintauer T., McKenzie B., and Matyjaszewski K. ACS Symp. Ser. 854 (2003) 130
70. Ando T., Kamigaito M., and Sawamoto M. Macromolecules 33 (2000) 5825
71. Fischer H.J. Polym. Sci.: Part A: Polym. Chem. 37 (1999) 1885
72. Fischer H. Chem. Rev. 101 (2001) 3581
73. Goto A., and Fukuda T. Prog. Polym. Sci. 29 (2004) 329
74. Tang W., Tsarevsky N.V., and Matyjaszewski K.J. Am. Chem. Soc. 128 (2006) 1598
75. Berry R.S., Reimann C.W., and Spokes G.N.J. Chem. Phys. 37 (1962) 2278
76. Berry R.S., and Reimann C.W.J. Chem. Phys. 38 (1963) 1540
77. Pandey J.D., and Saxena O.C.J. Chem. Soc. (A) (1969) 397
78. Gillies M.B., Matyjaszewski K., Norrby P.-O., Pintauer T., Poli R., and Richard P. Macromolecules 36 (2003) 8551
79. Tsarevsky N.V., Braunecker W.A., Brooks S.J., and Matyjaszewski K. Macromolecules 39 (2006) 6817
80. Tsarevsky N.V., Tang W., Brooks S.J., and Matyjaszewski K. ACS Symp. Ser. 944 (2006) 56
81. Lingane J.J. Chem. Rev. 29 (1941) 1
82. Stability constants of metal-ion complexes. suppl. No 1. Special Publication No 25. The Chemical Society: London, 1971.
83. Navon N., Golub G., Cohen H., Paoletti P., Valtancoli B., Bencini A., and Meyerstein D. Inorg. Chem. 38 (1999) 3484
84. Ambundo E.A., Deydier M.-V., Grall A.J., Aguera-Vega N., Dressel L.T., Cooper T.H., Heeg M.J., Ochrymowycz L.A., and Rorabacher D.B. Inorg. Chem. 38 (1999) 4233
85. Golub G., Lashaz A., Cohen H., Paoletti P., Bencini A., Valtancoli B., and Meyerstein D. Inorg. Chim. Acta 255 (1997) 111
86. Lever A.B.P. Inorg. Chem. 29 (1990) 1271
87. Lever A.B.P. In: McCleverty J.A., and Meyer T.J. (Eds). Comprehensive Coordination Chemistry II Vol. 2 (2004), Elsevier, Amsterdam 251-268
88. Pintauer T., and Matyjaszewski K. Coord. Chem. Rev. 249 (2005) 1155
89. In: Zanello P., and Bernal I.: I. (Eds). Stereochemical Control, Bonding and Steric Rearrangements Vol. 4 (1990), Elsevier, Amsterdam 181-366
90. Zhang C.X., Kaderli S., Costas M., Kim E.-i., Neuhold Y.-M., Karlin K.D., and Zuberbuehler A.D. Inorg. Chem. 42 (2003) 1807
91. Zhang C.X., Liang H.-C., Kim E.-i., Shearer J., Helton M.E., Kim E., Kaderli S., Incarvito C.D., Zuberbuehler A.D., Rheingold A.L., and Karlin K.D.J. Am. Chem. Soc. 125 (2003) 634
92. Hatcher L.Q., Vance M.A., Sarjeant A.A.N., Solomon E.I., and Karlin K.D. Inorg. Chem. 45 (2006) 3004
93. Addison A.W. Inorg. Chim. Acta 162 (1989) 217
94. Rorabacher D.B. Chem. Rev. 104 (2004) 651
95. Fenwick F.J. Am. Chem. Soc. 48 (1926) 860
96. Anderegg G. Helv. Chim. Acta 46 (1963) 2397
97. Ciavatta L., Ferri D., and Palombari R.J. Inorg. Nucl. Chem. 42 (1980) 593
98. Malyszko J., and Scendo M.J. Electroanal. Chem. 269 (1989) 113
99. Randles J.E.B.J. Chem. Soc. (1941) 802
100. Desmarquest J.P., Trinh-Dinh C., and Bloch O.J. Electroanal. Chem. 27 (1970) 101
101. Molodov A.I., Yanov L.A., and Golodnitskaya D.V. Elektrokhimiia 13 (1977) 300
102. Foll A., Le Demezet M., and Courtot-Coupez J.J. Electroanal. Chem. 35 (1972) 41
103. Ahrland S., Blauenstein P., Tagesson B., and Tuhtar D. Acta Chem. Scand. A 34 (1980) 265
104. Malyszko J., and Scendo M. Monatsh. Chem. 118 (1987) 435
105. Datta D. Indian J. Chem. 26 A (1987) 605
106. Ahrland S., Ishiguro S., and Persson I. I. Acta Chem. Scand. A 40 (1986) 418
107. Lewandowski A., and Malinska J. Electrochim. Acta 34 (1989) 333
108. Ahrland S., Nilsson K., and Tagesson B. Acta Chem. Scand. A 37 (1983) 193
109. Yanov L.A., and Molodov A.I. Elektrokhimiia 11 (1975) 1112
110. Singh P., MacLeod I.D., and Parker A.J.J. Solution Chem. 11 (1982) 495
111. Calligaris M., and Carugo O. Coord. Chem. Rev. 153 (1996) 83
112. Walton R.A. Quart. Rev. Chem. Soc. 19 (1965) 126
113. Storhoff B.N., and Lewis Jr. H.C. Coord. Chem. Rev. 23 (1977) 1
114. Schwarzenbach G. Die Komplexometrische Titration. second ed. (1956), Enke, Stuttgart
115. Ringbom A. Complexation in Analytical Chemistry (1963), Interscience, New York
116. Golub G., Cohen H., Paoletti P., Bencini A., Messori L., Bertini I., and Meyerstein D.J. Am. Chem. Soc. 117 (1995) 8353
117. Tsarevsky N.V., and Matyjaszewski K. ACS Symp. Ser. 937 (2006) 79
118. Paoletti P., Fabbrizzi L., and Barbucci R. Inorg. Chim. Acta Rev. 7 (1973) 43
119. Tsarevsky N.V., and Matyjaszewski K.J. Polym. Sci.: Part A: Polym. Chem. 44 (2006) 5098
120. Bernardo M.M., Heeg M.J., Schroeder R.R., Ochrymowycz L.A., and Rorabacher D.B. Inorg. Chem. 31 (1992) 191
121. Ahrland S., and Bjork N.O. Coord. Chem. Rev. 16 (1975) 115
122. Lewandowski A., and Malinska J. New J. Chem. 20 (1996) 653
123. Rudd D.P., and Taube H. Inorg. Chem. 10 (1971) 1543
124. Binstead R.A., Stultz L.K., and Meyer T.J. Inorg. Chem. 34 (1995) 546
125. Masllorens E., Rodriguez M., Romero I., Roglans A., Parella T., Benet-Buchholz J., Poyatos M., and Llobet A.J. Am. Chem. Soc. 128 (2006) 5306
126. Therien M.J., Ni C.L., Anson F.C., Osteryoung J.G., and Trogler W.C.J. Am. Chem. Soc. 108 (1986) 4037
127. Song L., and Trogler W.C.J. Am. Chem. Soc. 114 (1992) 3355
128. Griller D., and Wayner D.D.M. Pure & Appl. Chem. 61 (1989) 717
129. Wayner D.D.M., and Houmam A. Acta Chem. Scand. 52 (1998) 377
130. Daasbjerg K., Pedersen S.U., and Lund H. General Aspects of the Chemistry of Radicals. In: Alfassi Z.B. (Ed) (1999), Wiley, Chichester 385-427
131. Kern J.M., and Federlin P. Tetrahedron 34 (1978) 661
132. Niyazymbetov M.E., Rongfeng Z., and Evans D.H.J. Chem. Soc., Perkin Trans. 2 (1996) 1957
133. Isse A.A., and Gennaro A.J. Phys. Chem. A 108 (2004) 4180
134. Wayner D.D.M., McPhee D.J., and Griller D.J. Am. Chem. Soc. 110 (1988) 132
135. Wada K., and Hashimoto H. Bull. Chem. Soc. Jpn. 41 (1968) 3001
136. Jacobson R.R., Tyeklar Z., and Karlin K.D. Inorg. Chim. Acta 181 (1991) 111
137. Matyjaszewski K., Jo S.M., Paik H.-j., and Gaynor S.G. Macromolecules 30 (1997) 6398
138. Jakubowski W., and Matyjaszewski K. Angew. Chem., Int. Ed. 45 (2006) 4482
139. Jakubowski W., Min K., and Matyjaszewski K. Macromolecules 39 (2006) 39
140. Pietrasik J., Dong H., and Matyjaszewski K. Macromolecules 39 (2006) 6384
141. Kochi J.K. Science 155 (1967) 415
142. Kochi J.K. Acc. Chem. Res. 7 (1974) 351
143. Jenkins C.L., and Kochi J.K.J. Am. Chem. Soc. 94 (1972) 843
144. Jenkins C.L., and Kochi J.K.J. Am. Chem. Soc. 94 (1972) 856
145. Wada K., Yamashita J., and Hashimoto H. Bull. Chem. Soc. Jpn. 40 (1967) 2410
146. Matyjaszewski K., Davis K., Patten T.E., and Wei M. Tetrahedron 53 (1997) 15321
147. Lutz J.-F., and Matyjaszewski K. Macromol. Chem. Phys. 203 (2002) 1385
148. Lutz J.-F., and Matyjaszewski K.J. Polym. Sci.: Part A: Polym. Chem. 43 (2005) 897
149. Qiu J., and Matyjaszewski K. Macromolecules 30 (1997) 5643
150. Fuerstner A., and Shi N.J. Am. Chem. Soc. 118 (1996) 12349
151. Freiberg M., and Meyerstein D.J. Chem. Soc., Chem. Comm. (1977) 127
152. Ferraudi G. Inorg. Chem. 17 (1978) 2506
153. Matyjaszewski K., and Woodworth B.E. Macromolecules 31 (1998) 4718
154. Poli R., Stoffelbach F., and Maria S. Polym. Prepr. 46 2 (2005) 305
155. Poli R. Angew. Chem., Int. Ed. 45 (2006) 5058
156. W.A. Braunecker, B. Morelli, W.C. Brown, R. Poli, K. Matyjaszewski, in preparation.
157. Matyjaszewski K., Jakubowski W., Min K., Tang W., Huang J., Braunecker W.A., and Tsarevsky N.V. Proc. Natl. Acad. Sci. USA 103 (2006) 15309