Abstract
A series of three iron(III) salen complexes was synthesized and successfully used for copolymerization of cyclohexene oxide and phthalic anhydride. Catalytic systems based on an iron(III) salen complex in combination with 4-(dimethylamino)pyridine (DMAP) or bis(triphenylphosphine)iminium chloride (PPNCl) cocatalysts produced purely alternating copolymer with narrow molar mass distributions. [N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexylenediamine] iron(III) chloride was the most active complex and afforded the copolymer even in the absence of the cocatalysts. Other iron complexes were completely inactive in absence of a cocatalyst. Both DMAP and PPNCl alone were able to catalyze the copolymerization, affording purely alternating copolymers in good yields.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
I. Vroman and L. Tighzert, Materials, 2, 307 (2009).
R. F. Fischer, J. Polym. Sci., 44, 155 (1960).
T. Aida and S. Inoue, J. Am. Chem. Soc., 107, 1358 (1985).
Y. Maeda, A. Nakayama, N. Kawasaki, K. Hayashi, S. Aiba, and N. Yamamoto, Polymer, 38, 4719 (1997).
R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 123, 11498 (2001).
D. J. Darensbourg and J. C. Yarbrough, J. Am. Chem. Soc., 124, 6335 (2002).
M. Cheng, E. B. Lobkovsky, and G. W. Coates, J. Am. Chem. Soc., 120, 11018 (1998).
R. Reichardt, S. Vagin, R. Reithmeier, A. K. Ott, and B. Rieger, Macromolecules, 43, 9311 (2010).
L. R. Rieth, D. R. Moore, E. B. Lobkovsky, and G. W. Coates, J. Am. Chem. Soc., 124, 15239 (2002).
M. Zintl, F. Molnar, T. Urban, V. Bernhart, P. Preishuber-Pflügl, and B. Rieger, Angew. Chem. Int. Ed., 47, 3458 (2008).
A. M. DiCiccio and G. W. Coates, J. Am. Chem. Soc., 133, 10724 (2011).
E. H. Nejad, C. G. W. van Melis, T. J. Vermeer, C. E. Koning, and R. Duchateau, Macromolecules, 45, 1770 (2012).
R. C. Jeske, A. M. DiCiccio, and G. W. Coates, J. Am. Chem. Soc., 129, 11330 (2007).
N. E. Hosseini, A. Paoniasari, C. E. Koning, and R. Duchateau, Polym. Chem., 3, 1308 (2012).
E. H. Nejad, A. Paoniasari, C. G. W. van Melis, C. E. Koning, and R. Duchateau, Macromolecules, 46, 631 (2013).
J. Liu, Y.-Y. Bao, Y. Liu, W.-M. Ren, and X.-B. Lu, Polym. Chem., 4, 1439 (2013).
R. C. Jeske, J. M. Rowley, and G. W. Coates, Angew. Chem. Int. Ed., 47, 6041 (2008).
S. Huijser, E. HosseiniNejad, R. Sablong, C. D. Jong, C. E. Koning, and R. Duchateau, Macromolecules, 44, 1132 (2011).
A. Fuerstner, A. Leitner, M. Mendez, and H. Krause, J. Am. Chem. Soc., 124, 13856 (2002).
M. Bagherzadeh and M. Zare, J. Sulfur Chem., 32, 335 (2011).
J. P. Collman, L. Zeng, and J. I. Brauman, Inorg. Chem., 43, 2672 (2004).
R. Odhiambo, G. Muthakia, and S. Kagwanja, Transit. Metal. Chem., 37, 431 (2012).
G. Socrates, Infrared and Raman Characteristic Group Frequencies: Tables and Charts, 3rd ed., John Wiley & Sons, Chichester, 2004.
D. J. Darensbourg, R. R. Poland, and C. Escobedo, Macromolecules, 45, 2242 (2012).
D. J. Darensbourg, Chem. Rev., 107, 2388 (2007).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mundil, R., Hošt’álek, Z., Šeděnková, I. et al. Alternating ring-opening copolymerization of cyclohexene oxide with phthalic anhydride catalyzed by iron(III) salen complexes. Macromol. Res. 23, 161–166 (2015). https://doi.org/10.1007/s13233-015-3022-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13233-015-3022-4