Abstract
Ferrocene-containing polymers (FcPs) have attracted much research interest in the last decade, due to their unique properties and enormous applications. However, it is a great synthetic challenge to prepare FcPs before the advent of click chemistry. In this review, we summarized the recent research efforts on synthesizing FcPs through click reactions, which include click modification of preformed polymers and click polymerization of ferrocene (Fc) containing monomers. Due to the containing Fc moieties, the FcPs enjoy excellent redox activity, thermal stability, electrochemical property, and magnetism. Accordingly, they are promising to be used as electrochemical sensors, catalysts, magneto-ceramics, electrode modifiers, optical devices, etc.
References
A.S. Abd-El-Aziz, P.O. Shipman, B.N. Boden, W.S. McNeil, Prog. Polym. Sci. 35, 714 (2010)
K.A. Williams, A.J. Boydston, C.W. Bielawski, Chem. Soc. Rev. 36, 729 (2007)
C.K.A. Gregson, V.C. Gibson, N.J. Long, E.L. Marshall, P.J. Oxford, A.J.P. White, J. Am. Chem. Soc. 128, 7410 (2006)
G.R. Newkome, E. He, C.N. Moorefield, Chem. Rev. 99, 1689 (1999)
V. Ganesh, V.S. Sudhir, T. Kundu, S. Chandrasekaran, Chem. Asian J. 6, 2670 (2011)
J.Q. Lu, T.E. Kopley, N. Moll, D. Roitman, D. Chamberlin, Q. Fu, J. Liu, T.P. Russell, D.A. Rider, I. Manners, M.A. Winnik, Chem. Mater. 17, 2227 (2005)
D.J. Caruana, A. Heller, J. Am. Chem. Soc. 121, 769 (1999)
P.L. Pauson, J. Am. Chem. Soc. 76, 2187 (1954)
G. Wilkinson, J. Organomet. Chem. 100, 273 (1975)
E.W. Neuse, L. Bednarik, Macromolecules 12, 187 (1979)
F. Wurm, F.J.L. Villanueva, H. Frey, J. Polym. Sci. Part A 47, 2518 (2009)
C. Ornelas, J. Ruiz, C. Belin, D. Astruc, J. Am. Chem. Soc. 131, 590 (2009)
J.O. Enlow, H. Jiang, J.T. Grant, K. Eyink, W. Su, T.J. Bunning, Polymer 49, 4042 (2008)
M. Cazacu, G. Munteanu, C. Racles, A. Vlad, M. Marcu, J. Organomet. Chem. 691, 3700 (2006)
J.C. Eloi, D.A. Rider, J.Y. Wang, T.P. Russell, I. Manners, Macromolecules 41, 9474 (2008)
R. Jain, R.A. Lalancette, J.B. Sheridan, Organometallics 24, 1458 (2005)
N. Zhou, Z. Zhang, J. Zhu, Z. Cheng, X. Zhu, Macromolecules 42, 3898 (2009)
F.S. Arimoto, A.C. Hven, J. Am. Chem. Soc. 77(23), 6295 (1955)
C.U. Pittman, J.C. Lai, D.P. Vanderpool, M. Good, R. Prado, Macromolecules 3, 746 (1970)
D.L. Compton, T.B. Rauchfuss, Organometallics 13, 4367 (1994)
M.A. Buretea, T.D. Tilley, Organometallics 16, 1507 (1997)
R.W. Heo, F.B. Somoza, T.R. Lee, J. Am. Chem. Soc. 120, 1621 (1998)
P. Nguyen, P. Gomez-Elipe, I. Manners, Chem. Rev. 99, 1515 (1999)
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)
Z. Li, J.W.Y. Lam, Y.Q. Dong, Y.P. Dong, H.H.Y. Sung, I.D. Williams, B.Z. Tang, Macromolecules 39, 6458 (2006)
J. Shi, C.K.W. Jim, F. Mahtab, J. Liu, J.W.Y. Lam, H.H.Y. Sung, I.D. Williams, Y. Dong, B.Z. Tang, Macromolecules 43, 680 (2010)
C.K.W. Jim, J.W.Y. Lam, A. Qin, C.W.T. Leung, J. Liu, H.H.Y. Sung, I.D. Williams, B.Z. Tang, J. Inorg. Organomet. Polym. Mater. 23, 147 (2013)
H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40, 2004 (2001)
V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596 (2002)
C.W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 67, 3057 (2002)
R. Hoogenboom, Angew. Chem. Int. Ed. 49, 3415 (2010)
P.L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 39, 1338 (2010)
D. Fournier, R. Hoogenboom, U.S. Schubert, Chem. Soc. Rev. 36, 1369 (2007)
Y. Yagci, M.A. Tasdelen, Prog. Polym. Sci. 31, 1133 (2006)
G.W. Goodal, W. Hayes, Chem. Soc. Rev. 35, 280 (2006)
B. Helms, J.L. Mynar, C.J. Hawker, J.M.J. Fréchet, J. Am. Chem. Soc. 126, 15020 (2004)
T. Hasegawa, M. Umeda, M. Numata, T. Fujisawa, S. Haraguchi, K. Sakurai, S. Shinkai, Chem. Lett. 35, 82 (2006)
H. Ritter, B. Knudsen, B.E. Mondrzik, R. Branscheid, U. Kolb, Polym. Int. 61, 1245 (2012)
S. Eyley, S. Shariki, S.E.C. Dale, S. Bending, F. Marken, W. Thielemans, Langmuir 28, 6514 (2012)
C.K.W. Jim, A. Qin, J.W.Y. Lam, M. Häußler, B.Z. Tang, J. Inorg. Organomet. Polym. Mater. 17, 289 (2007)
C.K.W. Jim, A. Qin, F. Mahtab, J.W.Y. Lam, B.Z. Tang, Chem. Asian J. 6, 2753 (2011)
J. Xu, Y. Tian, R. Peng, Y. Xian, Q. Ran, L. Jin, Electrochem. Commun. 11, 1972 (2009)
E. Scavetta, R. Mazzoni, F. Mariani, R.G. Margutta, A. Bonfiglio, M. Demelas, S. Fiorilli, M. Marzocchid, B. Frabonid, J. Mater. Chem. B 2, 2861 (2014)
P. Camurlu, N. Karagoren, React. Funct. Polym. 73, 847 (2013)
Z. Bicil, P. Camurlu, B. Yucel, B. Becer, J. Polym. Res. 20, 228 (2013)
M. Pawlak, E. Grygolowicz-Pawlak, E. Bakker, Anal. Chem. 82, 6887 (2010)
O. Karagollu, M. Gorur, F. Gode, B. Sennik, F. Yilmaz, Sens. Actuators, B 193, 788 (2014)
I. Martínez-Montero, S. Bruña, A.M. González-Vadillo, I. Cuadrado, Macromolecules 47, 1301 (2014)
B.Y. Kim, E.L. Ratcliff, N.R. Armstrong, T. Kowalewski, J. Pyun, Langmuir 26, 2083 (2010)
B. Yu, H.Y. Hu, D.A. Wang, W.T.S. Huck, F. Zhou, W.M. Liu, J. Mater. Chem. 19, 8129 (2009)
Y.F. Wu, S.Q. Liu, L. He, Anal. Chem. 81, 7015 (2009)
Z.B. Zhang, S.J. Yuan, X.L. Zhu, K.G. Neoh, E.T. Kang, Biosens. Bioelectron. 25, 1102 (2010)
L. Xu, D. Wan, H.F. Gong, K. Neoh, E. Kang, G. Fu, Langmuir 26, 15376 (2010)
G. Rydzek, A. Parat, P. Polavarapu, C. Baehr, J. Voegel, J. Hemmerlé, B. Senger, B. Frisch, P. Schaaf, L. Jierry, F. Boulmedais, Soft Matter 8, 446 (2012)
G. Rydzek, T. Garnier, P. Schaaf, J. Voegel, B. Senger, B. Frisch, Y. Haikel, C. Petit, G. Schlatter, L. Jierry, F. Boulmedais, Langmuir 29, 10776 (2013)
C. Ornelas, J.R. Aranzaes, E. Cloutet, S. Alves, D. Astruc, Angew. Chem. Int. Ed. 46, 872 (2007)
C. Ornelas, L. Salmon, J.R. Aranzaes, D. Astruc, Chem. Commun. 46, 4946 (2007)
C. Ornelas, J.R. Aranzaes, L. Salmon, D. Astruc, Chem. Eur. J. 14, 50 (2008)
J. Camponovo, J. Ruiz, E. Cloutet, D. Astruc, Chem. Eur. J. 15, 2990 (2009)
D. Astruc, C. Ornelas, J.R. Aranzaes, J. Inorg. Organomet. Polym. 18, 4 (2008)
D. Astruc, C. Ornelas, J. Ruiz, Acc. Chem. Res. 41, 841 (2008)
I. Javakhishvili, S. Hvilsted, Polym. Chem. 1, 1650 (2010)
O. Eren, M. Gorur, B. Keskin, F. Yilmaz, React. Funct. Polym. 73, 244 (2013)
J. Liu, J.W.Y. Lam, C.K.W. Jim, J.C.Y. Ng, J. Shi, H. Su, K.F. Yeung, Y. Hong, M. Faisal, Y. Yu, K.S. Wong, B.Z. Tang, Macromolecules 44, 68 (2011)
C. Lang, D. Voll, A.J. Inglis, N. Dingenouts, A.S. Goldmann, L. Barner, C. Barner-Kowollik, Macromol. Chem. Phys. 212, 831 (2011)
A. Qin, L. Tang, J.W.Y. Lam, C.K.W. Jim, Y. Yu, H. Zhao, J.Z. Sun, B.Z. Tang, Adv. Funct. Mater. 19, 1891 (2009)
C.K.W. Jim, A. Qin, J.W.Y. Lam, F. Mahtab, Y. Yu, B.Z. Tang, Adv. Funct. Mater. 20, 1319 (2010)
B. Yao, J. Mei, J. Li, J. Wang, H. Wu, J.Z. Sun, A. Qin, B.Z. Tang, Macromolecules 47, 1325 (2014)
H. Li, H. Wu, E. Zhao, J. Li, J.Z. Sun, A. Qin, B.Z. Tang, Macromolecules 46, 3907 (2013)
Q. Wei, J. Wang, X. Shen, X. Zhang, J.Z. Sun, A. Qin, B.Z. Tang, Sci. Rep. 3, 1093 (2013)
Q. Wang, H. Li, Q. Wei, J.Z. Sun, J. Wang, X. Zhang, A. Qin, B.Z. Tang, Polym. Chem. 4, 1396 (2013)
H. Li, J. Wang, J.Z. Sun, R. Hu, A. Qin, B.Z. Tang, Polym. Chem. 3, 1075 (2012)
H. Li, L. Li, H. Wu, J.W.Y. Lam, J.Z. Sun, A. Qin, B.Z. Tang, Polym. Chem. 4, 5537 (2013)
Acknowledgments
This work was partially supported by the National Science Foundation of China (21222402 and 21174120); the key project of the Ministry of Science and Technology of China (2013CB834702), and the Research Grants Council of Hong Kong (604711, 602212 and HKUST2/CRF/10). A. Q. and B.Z.T. thank the support from Guangdong Innovative Research Team Program (201101C0105067115).
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Yao, B., Sun, J.Z., Qin, A. et al. Click Chemistry: A Powerful and Versatile Methodology for Preparation of Ferrocene-Containing Polymers. J Inorg Organomet Polym 25, 37–46 (2015). https://doi.org/10.1007/s10904-014-0106-0
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DOI: https://doi.org/10.1007/s10904-014-0106-0