Sequential Modification of ADMET Polyketone via Oxime Chemistry and Electrophilic Alkoxyetherification
Fu-Rong Zeng A , Qi-Lin Zhu A and Zi-Long Li A BA Department of Chemistry, College of Science, Huazhong Agricultural University, Wuhan, Hubei 430070, China.
B Corresponding author. Email: lizilong@mail.hzau.edu.cn
Australian Journal of Chemistry 71(6) 449-454 https://doi.org/10.1071/CH18120
Submitted: 19 March 2018 Accepted: 29 April 2018 Published: 17 May 2018
Abstract
Post-polymerization modification is a facile and efficient method for the generation of diverse functional polymers. Herein, polymer-based molecular arrays were obtained by using sequential modification. First, periodic polyketone P0 was synthesized via acyclic diene metathesis (ADMET) polymerization of α,ω-diene M0. Oxime chemistry was employed in the functionalization of the ketone moieties of P0 using three commercially available alkoxyamine hydrochlorides. Finally, electrophilic alkoxyetherification, a four-component reaction, was employed in the modification of alkene groups on polymer main chains using N-bromosuccinimide (NBS), tetrahydrofuran, and fluorinated carboxylic acid. Complete conversion of reactive sites was observed in both steps, and the two modification reactions exhibited excellent compatibility. The thermal properties of the polymers as thermal stability, and glass transition and melting behaviours were investigated by thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC).
References
[1] A. Nakamura, T. M. J. Anselment, J. Claverie, B. Goodall, R. F. Jordan, S. Mecking, B. Rieger, A. Sen, P. W. N. M. van Leeuwen, K. Nozaki, Acc. Chem. Res. 2013, 46, 1438.| Crossref | GoogleScholarGoogle Scholar |
[2] L. Caire da Silva, G. Rojas, M. D. Schulz, K. B. Wagener, Prog. Polym. Sci. 2017, 69, 79.
| Crossref | GoogleScholarGoogle Scholar |
[3] E. Blasco, M. B. Sims, A. S. Goldmann, B. S. Sumerlin, C. Barner-Kowollik, Macromolecules 2017, 50, 5215.
| Crossref | GoogleScholarGoogle Scholar |
[4] (a) M. M. Brubaker, D. D. Coffman, H. H. Hoehn, J. Am. Chem. Soc. 1952, 74, 1509.
| Crossref | GoogleScholarGoogle Scholar |
(b) E. Drent, J. A. M. van Broekhoven, M. J. Doyle, J. Organomet. Chem. 1991, 417, 235.
| Crossref | GoogleScholarGoogle Scholar |
(c) E. Drent, P. H. M. Budzelaar, Chem. Rev. 1996, 96, 663.
| Crossref | GoogleScholarGoogle Scholar |
(d) S. DeVito, S. Bronco, Polym. Degrad. Stabil. 1999, 63, 399.
| Crossref | GoogleScholarGoogle Scholar |
(e) E. Drent, R. van Dijk, R. van Ginkel, B. van Oort, R. I. Pugh, Chem. Commun. 2002, 964.
| Crossref | GoogleScholarGoogle Scholar |
(f) A. K. Hearley, R. J. Nowack, B. Rieger, Organometallics 2005, 24, 2755.
| Crossref | GoogleScholarGoogle Scholar |
(g) L. Bettucci, C. Bianchini, C. Claver, E. J. Garcia Suarez, A. Ruiz, A. Meli, W. Oberhauser, Dalton Trans. 2007, 5590.
| Crossref | GoogleScholarGoogle Scholar |
(h) D. K. Newsham, S. Borkar, A. Sen, D. M. Conner, B. L. Goodall, Organometallics 2007, 26, 3636.
| Crossref | GoogleScholarGoogle Scholar |
(i) R. Luo, D. K. Newsham, A. Sen, Organometallics 2009, 28, 6994.
| Crossref | GoogleScholarGoogle Scholar |
(j) E. J. García Suárez, C. Godard, A. Ruiz, C. Claver, Eur. J. Inorg. Chem. 2007, 2582.
| Crossref | GoogleScholarGoogle Scholar |
(k) S. S. Soomro, D. Cozzula, W. Leitner, H. Vogt, T. E. Müller, Polym. Chem. 2014, 5, 3831.
| Crossref | GoogleScholarGoogle Scholar |
[5] (a) M. D. Watson, K. B. Wagener, Macromolecules 2000, 33, 3196.
| Crossref | GoogleScholarGoogle Scholar |
(b) P. Ortmann, F. P. Wimmer, S. Mecking, ACS Macro Lett. 2015, 4, 704.
| Crossref | GoogleScholarGoogle Scholar |
[6] (a) J. Collins, Z. Xiao, M. Müllner, L. A. Connal, Polym. Chem. 2016, 7, 3812.
| Crossref | GoogleScholarGoogle Scholar |
(b) D. K. Kölmel, E. T. Kool, Chem. Rev. 2017, 117, 10358.
| Crossref | GoogleScholarGoogle Scholar |
[7] (a) K. Brzezinska, K. B. Wagener, Macromolecules 1992, 25, 2049.
| Crossref | GoogleScholarGoogle Scholar |
(b) Z.-L. Li, A. Lv, F.-S. Du, Z.-C. Li, Macromolecules 2014, 47, 5942.
| Crossref | GoogleScholarGoogle Scholar |
(c) J. A. van Hensbergen, T. W. Gaines, K. B. Wagener, R. P. Burford, A. B. Lowe, Polym. Chem. 2014, 5, 6225.
| Crossref | GoogleScholarGoogle Scholar |
(d) M. Unverferth, M. A. R. Meier, Polymer 2014, 55, 5571.
| Crossref | GoogleScholarGoogle Scholar |
(e) L. Vlaminck, K. De Bruycker, O. Türünç, F. E. Du Prez, Polym. Chem. 2016, 7, 5655.
| Crossref | GoogleScholarGoogle Scholar |
(f) G. Becker, L. Vlaminck, M. M. Velencoso, F. E. Du Prez, F. R. Wurm, Polym. Chem. 2017, 8, 4074.
| Crossref | GoogleScholarGoogle Scholar |
[8] (a) C. M. Geiselhart, J. T. Offenloch, H. Mutlu, C. Barner-Kowollik, ACS Macro Lett. 2016, 5, 1146.
| Crossref | GoogleScholarGoogle Scholar |
(b) J. T. Offenloch, J. Willenbacher, P. Tzvetkova, C. Heiler, H. Mutlu, C. Barner-Kowollik, Chem. Commun. 2017, 775.
| Crossref | GoogleScholarGoogle Scholar |
[9] (a) T. E. Hopkins, K. B. Wagener, Macromolecules 2003, 36, 2206.
| Crossref | GoogleScholarGoogle Scholar |
(b) S. Beer, I. Teasdale, O. Brueggemann, Polym. Degrad. Stabil. 2014, 110, 336.
| Crossref | GoogleScholarGoogle Scholar |
[10] P. A. Fokou, M. A. R. Meier, J. Am. Chem. Soc. 2009, 131, 1664.
| Crossref | GoogleScholarGoogle Scholar |
[11] Z.-L. Li, L. Li, X.-X. Deng, L.-J. Zhang, B.-T. Dong, F.-S. Du, Z.-C. Li, Macromolecules 2012, 45, 4590.
| Crossref | GoogleScholarGoogle Scholar |
[12] E. Boz, K. B. Wagener, A. Ghosal, R. Fu, R. G. Alamo, Macromolecules 2006, 39, 4437.
| Crossref | GoogleScholarGoogle Scholar |
[13] Z.-L. Li, A. Lv, L. Li, X.-X. Deng, L.-J. Zhang, F.-S. Du, Z.-C. Li, Polymer 2013, 54, 3841.
| Crossref | GoogleScholarGoogle Scholar |
