Synthesis and unexpected reactivity of iron tris(bipyridine) complexes with poly(ethylene glycol) macroligands

Biomacromolecules

Volumn 7, Issue 2, 2006, Pages 459-468

  Pfister, Anne ^a   Fraser, Cassandra L ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANIONIC POLYMERIZATION; CHELATION; COPOLYMERS; CROSSLINKING; DERIVATIVES; MACROMOLECULES; MOLECULAR WEIGHT; OXIDES; POLYETHYLENE GLYCOLS; SOLUTIONS; SYNTHESIS (CHEMICAL); TITRATION;

BIPYRIDINE; ETHYLENE OXIDE; HYDROXYL END GROUPS;

IRON COMPOUNDS;

ARGON; BIPYRIDINE DERIVATIVE; COPOLYMER; CROSS LINKING REAGENT; ETHYLENE OXIDE; FERROUS SULFATE; HYDROXYL GROUP; LIGAND; MACROGOL;

AQUEOUS SOLUTION; ARTICLE; BLEACHING; CHELATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHROMATOPHORE; CONTROLLED STUDY; KINETICS; MOLECULAR WEIGHT; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS; TITRIMETRY;

2,2'-DIPYRIDYL; FERROUS COMPOUNDS; KINETICS; LIGANDS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; POLYETHYLENE GLYCOLS; TIME FACTORS; TITRIMETRY;

EID: 33644603204     PISSN: 15257797     EISSN: None     Source Type: Journal    
DOI: 10.1021/bm050652l     Document Type: Article

References (116)

1. (a) Manners, I. Synthetic Metal-Containing Polymers; Wiley-VCH: Weinheim, Germany, 2004.
2. (b) Wöhrle, D.; Pomogailo, A. D. Metal Complexes and Metals in Macromolecules; Wiley-VCH: Weinheim, Germany, 2003.
3. Fraser, C. L.; Smith, A. P. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4704.
4. Schubert, U. S.; Eschbaumer, C. Angew. Chem., Int. Ed. 2002, 41, 2892.
5. Pollino, J. M.; Weck, M. Chem. Soc. Rev. 2005, 34, 193.
6. Shenhar, R.; Norsten, T. B.; Rotello, V. M. Adv. Mater. 2005, 17, 657.
7. Hofmeier, H.; Schubert, U. S. Chem. Commun. 2005, 19, 2423.
8. (a) Hjelm, J.; Handel, R. W.; Hagfeldt, A.; Constable, E. C.; Housecroft, C. E.; Forster, R. J. Inorg. Chem. 2005, 44, 1073.
9. (b) Gould, S.; Strouse, G. F.; Meyer, T. J.; Sullivan, B. P. Inorg. Chem. 1991, 30, 2942.
10. (a) Higley, M. N.; Pollino, J. M.; Hollenbeak, E.; Weck, M. Chem. Eur. J. 2005, 11, 2946.
11. (b) Hofmeier, H.; Hoogenboom, R.; Wouters, M. E. L.; Schubert, U. S. J. Am. Chem. Soc. 2005, 127, 2913.
12. Ogoshi, T.; Itoh, H.; Kim, K.-M.; Chujo, Y. Macromolecules 2002, 35, 334.
13. For examples, see Beck, J. B.; Ineman, J. M.; Rowan, S. J. Macromolecules 2005, 38, 5060 and references therein.
14. Andres, P. R.; Schubert, U. S. Adv. Mater. 2004, 16, 1043.
15. (a) Li, M.; Mann, S. J. Mater. Chem. 2004, 14, 2260.
16. (b) Arvizo, R. R.; Verma, A.; Rotello, V. M. Supramol. Chem. 2005, 17, 155.
17. (c) Hofmeier, H.; Pahnke, J.; Weidl, C. H.; Schubert, U. S. Biomacromolecules 2004, 5, 2055.
18. (d) Torchilin, V. Bioconjugate Chem. 1999, 10, 146.
19. (a) Bender, J. L.; Corbin, P. S.; Fraser, C. L.; Metcalf, D. H.; Richardson, F. S.; Thomas, E. L.; Urbas, A. M. J. Am. Chem. Soc. 2002, 124, 8526.
20. (b) Park, C.; McAlvin, J. E.; Fraser, C. L.; Thomas, E. L. Chem. Mater. 2002, 14, 1225.
21. Fustin, C.-A.; Lohmeijer, B. G. G.; Duwez, A.-S.; Jonas, A. M.; Schubert, U. S.; Gohy, J.-F. Adv. Mater. 2005, 17, 1162.
22. Zhou, G.; Harruna, I. I. Macromolecules 2005, 38, 4114.
23. For example, see Mann, S. Chem. Commun. 2004, 1, 1.
24. (a) Zimmermann, N.; Meggers, E.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 13684.
25. (b) Atwell, S.; Meggers, E.; Spraggon, G.; Schultz, P. G. J. Am. Chem. Soc. 2001, 123, 12364.
26. Popescu, D.-L.; Parolin, T. J.; Achim, C. J. Am. Chem. Soc. 2003, 125, 6354.
27. (a) Wang, C.; Stewart, R. J.; Kopecek, J. Nature 1999, 397, 417.
28. (b) For a related example, see Xu, C.; Breedveld, V.; Kopecek, J. Biomacromolecules 2005, 6, 1739.
29. Tor, Y. C. R. Chim. 2003, 6, 755.
30. For example, see (a) Gorczynski, J. L.; Chen, J.; Fraser, C. L. J. Am. Chem. Soc. 2005, 127, 14956.
31. (b) McAlvin, J. E.; Scott, S. B.; Fraser. C. L. Macromolecules 2000, 33, 6953.
32. For an interesting example of a temperature-sensitive metallopolymer, see Beck, J. B.; Rowan, S. J. J. Am. Chem. Soc. 2003, 125, 13922.
33. Zhao, Y.; Beck, J. B.; Rowan, S. J.; Jamieson, A. M. Macromolecules 2004, 37, 3529.
34. (a) Clarke, Y.; Xu, W.; Demas, J. N.; DeGraff, B. A. Anal. Chem. 2000, 72, 3468.
35. (b) Bare, W. D.; Mack, N. H.; Xu, W.; Demas, J. N.; DeGraff, B. A. Anal. Chem. 2002, 74, 2198.
36. (c) Parker, D.; Senanayake, K.; Williams, J. A. G. Chem. Commun. 1997, 18, 1777.
37. (a) Haskins-Glusac, K.; Pinto, M. R.; Tan, C.; Schanze, K. S. J. Am. Chem. Soc. 2004, 126, 14964.
38. (b) Han, B.-H.; Manners, I.; Winnik, M. A. Chem. Mater. 2005, 17, 3160.
39. (a) Wang, J.; Luthey-Schulten, Z. A.; Suslick, K. S. Proc. Natl. Acad. Sci. 2003, 100, 3035.
40. (b) Suslick, K. S.; Rakow, N. A.; Sen, A. Tetrahedron 2004, 60, 11133.
41. Demas, J. N.; DeGraff, B. A. Coord. Chem. Rev. 2001, 211, 317.
42. Fraser, C. L.; Smith, A. P. Comprehensive Coordination Chemistry II; Meyer, T. J., McCleverty, J. A., Eds; Elsevier Ltd.: Oxford, U.K., 2004; Vol. 1, Chapt. 1, pp 1-23.
43. Poly(ethylene glycol) Chemistry and Biological Applications; Harris, J. M., Zalipsky, S. Eds.; ACS Symposium Series 680; American Chemical Society: Washington, DC, 1997.
44. (a) Mrksich, M.; Whitesides, G. M. Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 55.
45. (b) Nath, N.; Hyun, J.; Ma, H.; Chilkoti, A. Surf. Sci. 2004, 570, 98.
46. (a) Duncan, R. Nat. Rev. 2003, 2, 347.
47. (b) Uhrich, K. E.; Cannizzaro, S. M.; Langer, R. S.; Shakesheff, K. M. Chem. Rev. 1999, 99, 3181.
48. Allen, T. M.; Cullis, P. R. Science 2004, 303, 1818.
49. (a) Hubbell, J. A. Curr. Opin. Biotechnol. 2003, 14, 551.
50. (b) Levenberg, S.; Langer, R. Curr. Top. Dev. Biol. 2004, 61, 113.
51. Roberts, M. J.; Bentley, M. D.; Harris, J. M. Adv. Drug Delivery Rev. 2002, 54, 459.
52. (a) Long, J. W.; Velazquez, C. S.; Murray, R. W. J. Phys. Chem. 1996, 100, 5492.
53. (b) Chujo, Y.; Naka, A.; Kraemer, M.; Sada, K.; Saegusa, T. J. Macromol. Sci., Pure Appl. Chem. 1995, A32, 1213.
54. (c) Naka, K.; Kobayashi, A.; Chujo, Y. Macromol. Rapid Commun. 1997, 18, 1025.
55. (d) Marin, V.; Holder, E.; Meier, M. A. R.; Hoogenboom, R.; Schubert, U. S. Macromol. Rapid Commun. 2004, 25, 793.
56. Schmatloch, S.; van den Berg, A. M. J.; Alexeev, A. S.; Hofmeier, H.; Schubert, U. S. Macromolecules 2003, 36, 9943.
57. (a) Zalipsky, S. Bioconjugate Chem. 1995, 6, 150.
58. (b) Akiyama, Y.; Otsuka, H.; Nagasaki, Y.; Kato, M.; Kataoka, K. Bioconjugate Chem. 2000, 11, 947.
59. Lee, Y.; Koo, H.; Jin, G.; Mo, H.; Cho, M. Y.; Park, J.-Y.; Choi, J. S.; Park, J. S. Biomacromolecules 2005, 6, 24.
60. For examples of responsive materials, see (a) Rehor, A.; Hubbell, J. A.; Tirelli, N. Langmuir 2005, 21, 411.
61. (b) Kost, J.; Langer, R. Adv. Drug Delivery Rev. 2001, 46, 125.
62. (c) Jeong, B.; Kim, S. W.; Bae, Y. H. Adv. Drug Delivery Rev. 2002, 54, 37.
63. Langer, R.; Tirrell, D. A. Nature 2004, 428, 487 and examples therein.
64. Hawker, P. N.; Twigg, M. V. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, U.K., 1987; Vol. 4, pp 1214-9.
65. Johnson, R. M.; Pfister, A.; Fraser, C. L. in Metal-Containing and Metallo-Supramolecular Polymers and Materials; Newkome, G. R., Manner, I., Schubert, U. S., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005; in press.
66. (a) Schaggar, R. S.; Hall, A. J.; Miller, J. D. Polymer 1996, 37, 5313.
67. (b) Viau, L.; Even, M.; Maury, O.; Haddleton, D. M.; Le Bozec, H. Macromol. Rapid Commun. 2003, 24, 630.
68. (c) Chujo, Y.; Sada, K.; Saegusa, T. Macromolecules 1993, 26, 6315.
69. (d) Card, R. J.; Neckers, D. C. Inorg. Chem. 1978, 17, 2345.
70. Johnson, R. M.; Fraser, C. L. Macromolecules 2004, 37, 2718.
71. (a) Groves, J. T. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3569.
72. (b) Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd ed.; Oxford University Press: Oxford, U.K., 1999.
73. Ma, W.; Li, J.; Tao, X.; He, J.; Xu, Y.; Yu, J. C.; Zhao, J. Angew. Chem., Int. Ed. 2003, 42, 1029.
74. Li, J.; Ma, W.; Huand, Y.; Tao, X.; Zhao, J.; Xu, Y. Appl. Catal. B: Environ. 2004, 48, 17.
75. Li, J.; Ma, W.; Huang, Y.; Cheng, M.; Zhao, J.; Yu, J. C. Chem. Commun. 2003, 2214.
76. Smith, A. P.; Corbin, P. S.; Fraser, C. L. Tetrahedron Lett. 2000, 41, 2787.
77. Jiang, Y. X.; Song, W. B., Liu, Y.; Wei, B.; Cao, X. C.; Xu, H. D. Mater. Chem. Phys. 2000, 62, 109.
78. Smith, A. P.; Fraser, C. L. Macromolecules 2003, 36, 2654.
79. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.
80. Yasuji, K.; Nakamura, T.; Nagasaki, Y.; Kato, M.; Kataoka, K. Macromolecules 1999, 32, 8024.
81. Hillmyer, M. A.; Bates, F. S. Macromolecules 1996, 29, 6994.
82. Goddu, R. F.; Hume, D. N. Anal. Chem. 1954, 26, 1740.
83. Knischka, R.; Lutz, P. J.; Sunder, A.; Mülhaupt, R.; Frey, H. Macromolecules 2000, 33, 315.
84. Angot, S.; Taton, D.; Gnanou, Y. Macromolecules 2000, 33, 5418.
85. Reed, N. N.; Janda, K. D. J. Org. Chem. 2000, 65, 5843.
86. Corbin, P. S.; Webb, M. P.; McAlvin, J. E.; Fraser, C. L. Biomacromolecules 2001, 2, 223.
87. 2 titration studies. After it stood in air for ∼6.5 h there was no detectable change in the concentration of iron(II) in the stock solution. However, titration of the iron stock solution with bpy after 1 day under ambient conditions indicates some loss of Fe(II) (86% of original amount). Thus, iron solutions were freshly prepared and titrated for each experiment.
88. (a) Bernson, A.; Lindgren, J.; Huang, W.; Frech, R. Polymer 1995, 36, 4471.
89. (b) Caminiti, R.; Carbone, M.; Panero, S.; Sadun, C. J. Phys. Chem. B 1999, 103, 10348.
90. (a) Wu, X.; Fraser, C. L. Macromolecules 2000, 33, 4053.
91. (b) Wu, X.; Fraser, C. L. Macromolecules 2000, 33, 7776.
92. (a) Hill, R. Proc. R. Soc. (London) 1930, B107, 205.
93. (b) Moss, M. L.; Mellon, M. G. Ind. Eng. Chem., Anal. Ed. 1942, 14, 862.
94. (c) Alexander, R. D.; Buisson, D. H.; Dudeney, W. L.; Irving, R. J. J. Chem. Soc., Faraday Trans. 1: Phys. Chem. Condensed Phases 1978, 74, 1081.
95. 4) exposed to air were stable after a month when monitored by UV-vis spectroscopy.
96. Krumholz, P. J. Am. Chem. Soc. 1949, 71, 3654.
97. Blandamer, M. J.; Burgess, J.; Chambers, J. G. J. Chem. Soc., Dalton Trans. 1976, 606.
98. Josceanu, A. M.; Moore, P. J. Chem. Soc., Dalton Trans. 1998, 369.
99. Nord, G.; Pedersen, B.; Bjergbakke, E. J. Am. Chem. Soc. 1983, 105, 1913.
100. Szacilowski, K.; Macyk, W.; Drzewiecka-Matuszek, A.; Brindell, M.; Stochel, G. Chem. Rev. 2005, 105, 2647.
101. (a) Wardman, P., Candeias, L. P. Radiat. Res. 1996, 145, 523.
102. (b) Liochev, S. I. In Metal Ions in Biological Systems; Sigel, A., Sigel, H., Eds.; Marcel Dekker: New York, 1999; Vol. 36, pp 1-39.
103. Welch, K. D.; Davis, T. Z.; Aust, S. D. Arch. Biochem. Biophys. 2002, 397, 360.
104. (a) Sobkowiak, A.; Narog, D.; Sawyer, D. T. J. Mol. Catal. A: Chem. 200, 159, 247.
105. (b) Lei, Z.-Q.; Wang, Y.-P. React. Polym. 1992, 16, 223.
106. Johnson, R. M.; Fraser, C. L.; Turro, C. Unpublished results.
107. Also see (a) Ferrere, S. Chem. Mater. 2000, 12, 1083.
108. (b) Nguyen, T. H.; Shannon, P. J.; Hoggard, P. E. Inorg. Chim. Acta 1999, 291, 136.
109. Brand, N.; Mailhot, G.; Bolte, M. Chemosphere 2000, 40, 395.
110. Kaczmarek, H.; Rabek, F. Angew. Makromol. Chem. 1997, 247, 111.
111. Duval, M.; Sarazin, D. Macromolecules 2003, 36, 1318.
112. (a) For an interesting example of an oxygen-sensitive gelation reaction that is facilitated by Fenton chemistry, see Goessl, A.; Tirelli, N.; Hubbell, J. A. J. Biomater. Sci., Polym. Ed. 2004, 15, 895.
113. (b) For a related example, see Napoli, A.; Valentini, M.; Tirelli, N.; Muller, M.; Hubbell, J. A. Nat. Mater. 2004, 3, 183.
114. Sawhney, A.; Pathak, C. P.; Hubbell, J. A. Macromolecules 1993, 26, 581.
115. Rydholm, A. E.; Bowman, C. N.; Anseth, K. S. Biomaterials 2005, 26, 4495.
116. Fuller, Z. J.; Bare, W. D.; Kneas, K. A.; Xu, W.-Y.; Demas, J. N.; DeGraff, B. A. Anal. Chem. 2003, 75, 2670.