Abstract
This review describes the synthesis of functional dimeric metal carbonyl complexes and their subsequent polymerization to afford polymers containing metal–metal bonds in the main chain. Such polymers are photodegradable because the metal–metal bonds are cleavable by visible light. The functionalization of the dimeric complexes and their polymerization is challenging due to the reactivity of the M–M bond, and therefore many standard synthesis and polymerization methods cannot be used. Various polymerization methods are discussed including ring-opening metathesis polymerization, acyclic diene metathesis polymerization, ring-opening polymerization, traditional step polymerization, and copper-catalyzed step polymerization using click chemistry.
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References
I. Manners, Synthetic Metal-Containing Polymers (Wiley–VCH, Weinheim, 2004)
D.R. Tyler, Coord. Chem. Rev. 246, 291 (2003)
S.C. Tenhaeff, Synthesis, Characterization, and Reactivity of Photosensitive Polymers (University of Oregon, 1991)
A. Kohler, H.F. Wittman, R.H. Friend, M.S. Kahn, J. Lewis, Synth. Met. 67, 245 (1994)
W. Lu, B.S. Mi, M.C.W. Chan, J. Am. Chem. Soc. 126, 4958 (2004)
C. Carraher, D. Siegmann-Louda, Biomedical Applications. Macromolecules Containing Metal and Metal-like Elements (Wiley, Hoboken, 2005)
A.S. Abd-El-Aziz, I. Manners, Frontiers in Metal-Containing Polymers (Wiley-Interscience, New Jersey, 2007)
I. Manners, Angew. Chem. Int. Ed. Engl. 35, 1602 (1996)
P. Nguyen, P. Gmez-Elipe, I. Manners, Chem. Rev. 99, 1515 (1999)
A.S. Abd-El-Aziz, C. Carraher, C.U. Pittman Jr., M. Zeldin, Inorganic and Organometallic Macromolecules; Design and Applications (Springer, New York, 2008)
D.R. Tyler, Mechanistic Aspects of the Photodegradation of Polymers Containing Metal–Metal Bonds Along Thier Backbones (John Wiley & Sons Inc., 2006)
B.C. Daglen, D.R. Tyler, Macromolecules 41, 9525 (2008)
D.R. Tyler, J.J. Wolcott, G.F. Nieckarz, S.C. Tenhaeff, ACS Symp. Ser. 572, 481 (1994)
C.U. Pittman, M.D. Rausch Jr., Pure Appl. Chem. 58, 617 (1986)
K.E. Gonsalves, R.W. Lenz, M.D. Rausch, Appl. Organomet. Chem. 81, 1 (1987)
K. Gonsalves, L. Zhan-Ru, M.D. Rausch, J. Am. Chem. Soc. 106, 3862 (1984)
F.W. Knobloch, W.H. Rauscher, J. Polym. Sci. 54, 651 (1961)
W.J. Patterson, S.P. McManus, C.U. Pittman Jr, J. Polym. Sci., Polym. Chem. Ed. 12, 837 (1974)
A.E. Stiegman, D.R. Tyler, Coord. Chem. Rev. 63, 217 (1985)
R. Birdwhistell, P. Hackett, A.R. Manning, J. Organomet. Chem. 157, 239 (1978)
G.V. Shultz, Polymerization Methods for the Synthesis of Photosensitive Organometallic Polymers with Mo–Mo Bonds in the Backbone (University of Oregon, 2009)
B.E. Lindfors, J.L. Male, K.J. Covert, D.R. Tyler, Chem. Commun. 1687 (1997)
T.S. Coolbaugh, R.J. Coots, B.D. Santarsiero, R.H. Grubbs, Inorg. Chim. Acta 98, 99 (1985)
S.C. Tenhaeff, D.R. Tyler, Organometallics 10, 1116 (1991)
C. Nataro, J. Angelici, Inorg. Chem. 37, 2975 (1998)
G.V. Shultz, O.R. Berryman, L.V. Zakharov, D.R. Tyler, J. Inorg. Organomet. Polym. Mater. 18, 149 (2008)
V. Riera, M.A. Ruiz, J. Organomet. Chem. 382, 407 (1990)
D.J. Brauer, J. Organomet. Chem. 321, 339 (1987)
K.A. Azam, A.J. Deeming, M.S. Felix, Polyhedron 7, 1793 (1988)
V. Riera, M.A. Miguel, Organometallics 11, 2854 (1992)
R. Chen, D.R. Tyler, Macromolecules 37, 5430 (2004)
S.C. Tenhaeff, D.R. Tyler, Organometallics 10, 473 (1991)
G.F. Nieckarz, The Synthesis, Characterization, and Photoreactivity of Polyamides and Bis-Amide Model Compounds Containing Mo–Mo Bonds (University of Oregon, Eugene, 1996)
M. Moran, M.C. Pascual, I. Cuadrado, J. Losada, Organometallics 12, 811 (1993)
M.D. Randles, N.T. Lucas, M.P. Cifuentes, M.G. Humphrey, M.K. Smith, A.C. Willis, M. Samoc, Macromolecuels 40, 7807 (2007)
N.T. Lucas, A.D. Rae, M.G. Humphrey, Macromolecules 34, 6188 (2001)
B.C. Daglen, D.R. Tyler, J. Inorg. Organomet. Polym. Mater. 19, 91 (2009)
B.C. Daglen, J.D. Harris, D.R. Tyler, J. Inorg. Organomet. Polym. Mater. 17, 267 (2007)
R.H. Grubbs, Angew. Chem. Int. Ed. 45, 3760 (2006)
Y. Chauvin, Angew. Chem. Int. Ed. 45, 3741 (2006)
S.H. Hong, R.H. Grubbs, J. Am. Chem. Soc. 128, 3508 (2006)
C. Wirth-Pfeifer, A. Michel, K. Wiess, Novel Metathesis Chemistry (Kluwer Academic Publishing, Boston, 2003)
G. Odian, Principles of Polymerization, 4th edn. (Wiley-Interscience, New Jersey, 2004)
J.E. Schwenderman, A.C. Church, K.B. Wagener, Adv. Syn. Catal. 344, 597 (2002)
I. Dragutan, V. Dragutan, H. Fischer, J. Inorg. Organomet. Polym. Mater. 15, 439 (2008)
J.D. Gilbertson, T.J.R. Weakley, F. Han, J.J. Wolcott, D.R. Tyler, J. Inorg. Organomet. Polym. Mater. 15, 439 (2005)
R.W. Heo, T.R. Somoza, T.R. Lee, J. Am. Chem. Soc. 120, 1621 (1998)
R.J. Haines, A.L. DuPreez, J. Organomet. Chem. 21, 181 (1970)
G.V. Shultz, J.M. Zemke, D.R. Tyler, Macromolecules 42, 7644 (2009)
J. Heck, K. Kriebisch, H. Mellinghoff, Chem. Ber. 121, 1753 (1988)
V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596 (2002)
M. Meldel, Macromol. Rapid Commun. 29, 1016 (2008)
H. Nandivada, X. Jiang, J. Lahann, Adv. Mater. 19, 2197 (2007)
X. Wang, A. Kimyonok, M. Weck, Chem. Commun. 3933 (2006)
C. Haensch, M. Chiper, C. Ulbricht, A. Winter, S. Hoeppner, U.S. Schubert, Langmuir 24, 12981 (2008)
K. Matyjaszewski, Y. Nakagawa, S.G. Gaynor, Macromol. Rapid Commun. 18, 2057 (1997)
Acknowledgments
Acknowledgment is made to the Petroleum Research Fund, administered by the American Chemical Society and to the National Science Foundation for the support of this research. This research was also supported by the National Science Foundation IGERT Fellowship Program under Grant No. DGE-0549503.
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Shultz, G.V., Tyler, D.R. Preparation of Functionalized Organometallic Metal–Metal Bonded Dimers Used in the Synthesis of Photodegradable Polymers. J Inorg Organomet Polym 19, 423–435 (2009). https://doi.org/10.1007/s10904-009-9307-3
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DOI: https://doi.org/10.1007/s10904-009-9307-3