Hülya ARSLAN, Yasemin KÜÇÜK, - Ayfer

A kinetic study of atom transfer radical polymerization of styrene with bis(2-pyridyl)ethylenedimethanimine derivative ligands

Atom transfer radical polymerization (ATRP) of styrene was carried out with multidentate nitrogen-based ligands, namely N,N'-bis[phenyl(pyrid-2-yl)methylene] ethane-1,2-diamine (BPDA) and N,N'-bis[methyl(pyrid-2-yl)methylene] ethane-1,2-diamine (BMDA), and catalyst systems at catalyst/ligand molar ratios of 1/0.33, 1/0.5, 1/1, and 1/1.5 by using 2 different initiators, (1-bromoethyl)benzene (BEB) and ethyl-2-bromopropionate (EBP). Linear first-order kinetic plots were observed for ATRP of styrene upon using BPDA as a ligand with both initiators. Even though the linear slopes indicate that radical concentration remains constant during reactions, high molecular weights were obtained at low conversion and showed a linear relation thereafter. To investigate the molecular weight effect, reactions were also performed in the presence of (1-bromoethyl)benzene initiator in dimethylformamide (DMF) for BPDA and in toluene for BMDA using a catalyst/ligand ratio of 1/1.

Anahtar Kelimeler:

Polymer synthesis, controlled radical polymerization, ATRP, imine ligand

A kinetic study of atom transfer radical polymerization of styrene with bis(2-pyridyl)ethylenedimethanimine derivative ligands

Keywords:

Polymer synthesis, controlled radical polymerization, ATRP, imine ligand,

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Wang, J. S.; Matyjaszewski K. J. Am. Chem. Soc. 1995, 117, 5614–5615.
Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721–1723.
Percec, V.; Barboiu B. Macromolecules 1995, 28, 7970–7972.
Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689–3746.
Quchi, M.; Terashima, T.; Sawamoto, M. Chem. Rev. 2009, 109, 4963–5050.
Lena, F.; Matyjaszewski, K. Prog. Polym. Sci. 2010, 35, 959–1021.
Pintauer, T.; Matyjaszewski, K. Coordin. Chem. Rev. 2005, 249, 1155–1184.
Tsarevsky, N. V.; Matyjaszewski, K. Chem. Rev. 2007, 107, 2270–2299.
Tang, W.; Matyjaszewski, K. Macromolecules 2006, 39, 4953–4959.
Davis, K. A.; Matyjaszewski, K. Macromolecules 2000, 33, 4039–4047.
Gurr, P. A.; Mills, M. F.; Qiao, G. G.; Solomon, D. H. Polymer 2005, 46, 2097–2104.
Muhlebach, A.; Gaynor, S. G.; Matyjaszewski, K. Macromolecules 1998, 31, 6046–6052.
Shen, Y.; Zhu, S.; Zeng, F.; Pelton, R. Macromolecules 2000, 33, 5427–5431.
Teodorescu, M.; Matyjaszewski, K. Macromolecules 1999, 32, 4826–4831.
Tsarevsky, N. V.; Braunecker, W. A.; Tang, W.; Brooks, S. J.; Matyjaszewski, K.; Weisman, G. R.; Wong, E. H. J. Mol. Catal. A-Chem. 2006, 257, 132–140.
Wootthikanokkhan, J.; Peesan, M.; Phinyocheep, P. Eur. Polym. J. 2001, 37, 2063–2071.
Brar, A. S.; Kaur, S. J. Polym. Sci. Pol. Chem. 2005, 43, 5906–5922.
Inoue, Y.; Matyjaszewski, K. Macromolecules 2004, 37, 4014–4021.
Zhang, H.; Klumperman, B.; van der Linde, R. Macromolecules 2002, 35, 2261–2267.
Zhang, H.; van der Linde, R. J. Polym. Sci. Pol Chem. 2002, 40, 3549–3561.
Haddleton, D. M.; Clark, A. J.; Crossman, M. C.; Duncalf, D. J.; Heming, A. M.; Morsley, S. R.; Shooter, A. J. Chem. Commun. 1997, 1173–1174.
Raghunadh, V.; Baskaran, D.; Sivaram, S. Polymer 2004, 45, 3149–3155.
Mittal, A.; Sivaram, S. J. Polym. Sci. Pol. Chem. 2005, 43, 4996–5008.
Haddleton, D. M.; Crossman, M. C.; Dana, B. H.; Duncalf, D. J.; Heming, A. M.; Kukulj, D.; Shooter, A. J. Macromolecules 1999, 32, 2110–2119.
Iovu, M.; Maithufi, N.; Mapolie, S. Macromol. Symp. 2003, 193, 209–226.
Haddleton, D. M.; Jackson, S. G.; Bon, S. A. F. J. Am. Chem. Soc. 2000, 122, 1542–1543.
Sarbu, T.; Lin, K.; Spanswick, J.; Gil, R. R.; Siegwart, D. J. Macromolecules 2004, 37, 9694–9700.
Cai, Y.; Hartenstein, M.; M¨ uller, A. H. E. Macromolecules 2004, 37, 7484–7490.
Chung, I. S.; Matyjaszewski, K. Macromolecules 2003, 36, 2995–2998.
Coessens, V.; Pintauer, T.; Matyjaszewski, K. Prog. Polym. Sci. 2001, 26, 337–377.
Yuan, X.; Lu, J.; Xu, Q.; Wang, L. Polymer 2005, 46, 9186–9191.
Muthukrishnan, S.; Jutz, G.; Andre, X.; Mori, H.; M¨ uller, A. H. E. Macromolecules 2005, 38, 9–18.
Muthukrishnan, S.; Mori, H.; M¨ uller, A. H. E. Macromolecules 2005, 38, 3108–3119.
Senkal, B. F.; Hizal, G.; Bicak, N. J. Polym. Sci. Pol. Chem. 2001, 39, 2691–2695.
Ydens, I.; Degee, P.; Dubois, P.; Libiszowski, J.; Duda, A.; Penczek, S. Macromol. Chem. Physic. 2003, 204, 171–179.
Beers, K. L.; Matyjaszewski, K. J. Macromol. Sci. Pure. Appl. Chem. 2001, 3, 731–739.
Zhang, Z.; Ying, S.; Zhang, Q.; Xu, X. J. Polym. Sci. Pol. Chem. 2001, 39, 2670–2676.
Batt-Coutrot, D.; Haddleton, D. M.; Jarvis, A. P.; Kelly, R. L. Eur Polym J. 2003, 39, 2243–2252.
Strissel, C.; Matyjaszewski, K.; Nuyken, O. Macromol. Chem. Physic. 2003, 204, 1169–1177.
Lee, S. B.; Russell, A. J.; Matyjaszewski, K. Biomacromolecules 2003, 4, 1386–1393.
Cassebras, M.; Pascual, S.; Polton, A.; Tardi, M.; Vairon, J. P. Macromol. Rapid Comm. 1999, 20, 261–264. Zhu, S.; Yan, D. Macromolecules 2000, 33, 8233–8238.
Zhang, M.; Breiner, T.; Mori, H.; M¨ uller, A. H. E. Polymer 2003, 44, 1449–1458.
Arslan, H.; Yesilyurt, N.; Hazer, B. J. Appl. Polym Sci. 2007, 106, 1742–1750.
Iovu, M. C.; Maithufi, N. G.; Mapolie, S. F. Polym. Int. 2003, 52, 899–907.
Acar, M. H.; Bicak, N. J. Polym. Sci. Pol. Chem. 2003, 41, 1677–1680.
Acar, M. H.; Becer, C. R.; Ondur, H. A.; Inceoglu, S. Polymer Preprints 2005, 46, 433–434.
Acar, M. H.; Becer, C. R.; Ondur, H. A.; Inceoglu, S. Alkylated linear amine ligands for homogeneous atom transfer radical polymerization; Matyjaszewski, K., Ed. ACS Symp. Series No. 944; Am. Chem. Soc.: Controlled/Living Radical Polymerization: From Synthesis to Materials, Washington, USA, 2006, pp. 98–110.
Zorvaryan, A.; Inceoglu, S.; Acar, M. H. Polymer 2011, 52, 617–621.
Mentes, A.; Sezek, S.; Hanhan, M. E.; B¨ uy¨ ukg¨ ung¨ or O. Turk. J. Chem. 2007, 31, 667–676.
Hong, S. C.; Matyjaszewski, K. Macromolecules 2002, 35, 7592–7605.
Zhu, C. Y.; Sun, F.; Zhang, M.; Jin, R. Polymer 2004, 45, 1141–1146.