Organocatalytic Synthesis of Alkyne-Functional Aliphatic Polycarbonates via Ring-Opening Polymerization of an Eight-Membered-N-Cyclic Carbonate
Panagiotis Bexis
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK
Search for more papers by this authorJulien De Winter
Organic Synthesis and Mass Spectrometry Laboratory, Interdisciplinary Center for Mass Spectrometry (CISMa), University of Mons, Place du Parc 23, Mons, B-7000 Belgium
Search for more papers by this authorMaria C. Arno
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK
Search for more papers by this authorCorresponding Author
Olivier Coulembier
Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons, Place du Parc 23, Mons, B-7000 Belgium
E-mail: [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Andrew P. Dove
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK
E-mail: [email protected]; [email protected]
Search for more papers by this authorPanagiotis Bexis
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK
Search for more papers by this authorJulien De Winter
Organic Synthesis and Mass Spectrometry Laboratory, Interdisciplinary Center for Mass Spectrometry (CISMa), University of Mons, Place du Parc 23, Mons, B-7000 Belgium
Search for more papers by this authorMaria C. Arno
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK
Search for more papers by this authorCorresponding Author
Olivier Coulembier
Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons, Place du Parc 23, Mons, B-7000 Belgium
E-mail: [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Andrew P. Dove
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK
E-mail: [email protected]; [email protected]
Search for more papers by this authorAbstract
The synthesis of well-defined propargyl-functional aliphatic polycarbonates is achieved via the organocatalytic ring-opening polymerization of prop-2-yn-1-yl 2-oxo-1,3,6-dioxazocane-6-carboxylate (P-8NC) using a wide variety of commercially available or readily made, shelf-stable organocatalysts. The resulting homopolymers show low dispersities and end-group fidelity, with the versatility of the system being demonstrated by the synthesis of telechelic copolymers and block copolymers with molar mass up to 40 kDa.
Conflict of Interest
The authors declare no conflict of interest.
Supporting Information
Filename | Description |
---|---|
marc202000378-sup-0001-SuppMat.pdf1.3 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1M. R. Gregory, Philos. Trans. R. Soc., B 2009, 364, 2013.
- 2R. U. Halden, Annu. Rev. Public Health 2010, 31, 179.
- 3X. Zhang, M. Fevre, G. O. Jones, R. M. Waymouth, Chem. Rev. 2018, 118, 839.
- 4D. K. Schneiderman, M. A. Hillmyer, Macromolecules 2017, 50, 3733.
- 5F. Nederberg, E. F. Connor, M. Möller, T. Glauser, J. L. Hedrick, Angew. Chem., Int. Ed. 2001, 40, 2712.
10.1002/1521-3773(20010716)40:14<2712::AID-ANIE2712>3.0.CO;2-Z CAS PubMed Web of Science® Google Scholar
- 6D. Bourissou, B. Martin-Vaca, A. Dumitrescu, M. Graullier, F. Lacombe, Macromolecules 2005, 38, 9993.
- 7A. P. Dove, R. C. Pratt, B. G. G. Lohmeijer, R. M. Waymouth, J. L. Hedrick, J. Am. Chem. Soc. 2005, 127, 13798.
- 8B. G. G. Lohmeijer, R. C. Pratt, F. Leibfarth, J. W. Logan, D. A. Long, A. P. Dove, F. Nederberg, J. Choi, C. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 8574.
- 9R. C. Pratt, B. G. G. Lohmeijer, D. A. Long, R. M. Waymouth, J. L. Hedrick, J. Am. Chem. Soc. 2006, 128, 4556.
- 10L. Zhang, F. Nederberg, R. C. Pratt, R. M. Waymouth, J. L. Hedrick, C. G. Wade, Macromolecules 2007, 40, 4154.
- 11S. Gazeau-Bureau, D. Delcroix, B. Martín-Vaca, D. Bourissou, C. Navarro, S. Magnet, Macromolecules 2008, 41, 3782.
- 12R. Kakuchi, Y. Tsuji, K. Chiba, K. Fuchise, R. Sakai, T. Satoh, T. Kakuchi, Macromolecules 2010, 43, 7090.
- 13N. Nomura, A. Akita, R. Ishii, M. Mizuno, J. Am. Chem. Soc. 2010, 132, 1750.
- 14D. J. Coady, K. Fukushima, H. W. Horn, J. E. Rice, J. L. Hedrick, Chem.Comm. 2011, 47, 3105.
- 15C. Wang, Y. Xiao, A. Heise, M. Lang, J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 5293.
- 16C. Thomas, F. Peruch, B. Bibal, RSC Adv. 2012, 2, 12851.
- 17R. Todd, G. Rubio, D. J. Hall, S. Tempelaar, A. P. Dove, Chem. Sci. 2013, 4, 1092.
- 18X. Zhang, G. O. Jones, J. L. Hedrick, R. M. Waymouth, Nat. Chem. 2016, 8, 1047.
- 19B. Lin, R. M. Waymouth, J. Am. Chem. Soc. 2017, 139, 1645.
- 20N. Spassky, M. Wisniewski, C. Pluta, A. Le Borgne, Macromol. Chem. Phys. 1996, 197, 2627.
- 21T. M. Ovitt, G. W. Coates, J. Am. Chem. Soc. 1999, 121, 4072.
- 22T. M. Ovitt, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 1316.
- 23Z. Zhong, P. J. Dijkstra, J. Feijen, Angew. Chem., Int. Ed. 2002, 41, 4510.
10.1002/1521-3773(20021202)41:23<4510::AID-ANIE4510>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 24K. Mikami, A. T. Lonnecker, T. P. Gustafson, N. F. Zinnel, P. J. Pai, D. H. Russell, K. L. Wooley, J. Am. Chem. Soc. 2013, 135, 6826.
- 25S. Tempelaar, I. A. Barker, V. X. Truong, D. J. Hall, L. Mespouille, P. Dubois, A. P. Dove, Polym. Chem. 2013, 4, 174.
- 26S. Tempelaar, L. Mespouille, P. Dubois, A. P. Dove, Macromolecules 2011, 44, 2084.
- 27R. Wang, W. Chen, F. Meng, R. Cheng, C. Deng, J. Feijen, Z. Zhong, Macromolecules 2011, 44, 6009.
- 28H. Zhang, X. Lin, S. Chin, M. W. Grinstaff, J. Am. Chem. Soc. 2015, 137, 12660.
- 29J. M. W. Chan, X. Ke, H. Sardon, A. C. Engler, Y. Y. Yang, J. L. Hedrick, Chem. Sci. 2014, 5, 3294.
- 30A. C. Engler, J. M. W. Chan, D. J. Coady, J. M. O'Brien, H. Sardon, A. Nelson, D. P. Sanders, Y. Y. Yang, J. L. Hedrick, Macromolecules 2013, 46, 1283.
- 31P. Olsén, K. Odelius, A.-C. Albertsson, Macromolecules 2014, 47, 6189.
- 32R. J. Ono, S. Q. Liu, S. Venkataraman, W. Chin, Y. Y. Yang, J. L. Hedrick, Macromolecules 2014, 47, 7725.
- 33S. Tempelaar, L. Mespouille, O. Coulembier, P. Dubois, A. P. Dove, Chem. Soc. Rev. 2013, 42, 1312.
- 34J. Mindemark, T. Bowden, Polym. Chem. 2012, 3, 1399.
- 35J. V. Olsson, D. Hult, Y. Cai, S. Garcia-Gallego, M. Malkoch, Polym. Chem. 2014, 5, 6651.
- 36R. Pratt, F. Nederberg, R. M. Waymouth, J. L. Hedrick, Chem. Commun. 2008, 114.
- 37S. Venkataraman, V. W. Ng, D. J. Coady, H. W. Horn, G. O. Jones, T. S. Fung, H. Sardon, R. M. Waymouth, J. L. Hedrick, Y. Y. Yang, J. Am. Chem. Soc. 2015, 137, 13851.
- 38S. Venkataraman, N. Veronica, Z. X. Voo, J. L. Hedrick, Y. Y. Yang, Polym. Chem. 2013, 4, 2945.
- 39A. Pascual, J. P. K. Tan, A. Yuen, J. M. W. Chan, D. J. Coady, D. Mecerreyes, J. L. Hedrick, Y. Y. Yang, H. Sardon, Biomacromolecules 2015, 16, 1169.
- 40S. Venkataraman, V. W. L. Ng, D. J. Coady, H. W. Horn, G. O. Jones, T. S. Fung, H. Sardon, R. M. Waymouth, J. L. Hedrick, Y. Y. Yang, J. Am. Chem. Soc. 2015, 137, 13851.
- 41Y. A. Chang, A. E. Rudenko, R. M. Waymouth, ACS Macro Lett. 2016, 5, 1162.
- 42F. Y. Qiu, L. Yu, F. S. Du, Z. C. Li, Macromol. Rapid Commun. 2017, 38, 1700400.
- 43S. Venkataraman, J. P. K. Tan, V. W. L. Ng, E. W. P. Tan, J. L. Hedrick, Y. Y. Yang, Biomacromolecules 2017, 18, 178.
- 44A. Y. Yuen, E. Lopez-Martinez, E. Gomez-Bengoa, A. L. Cortajarena, R. H. Aguirresarobe, A. Bossion, D. Mecerreyes, J. L. Hedrick, Y. Y. Yang, H. Sardon, ACS Biomater. Sci. Eng. 2017, 3, 1567.
- 45S. Venkataraman, K. P. Mineart, V. M. Prabhu, J. L. Hedrick, Y. Y. Yang, Polym. Chem. 2018, 9, 2434.
- 46S. Tempelaar, L. Mespouille, P. Dubois, A. P. Dove, Macromolecules 2011, 44, 2084.
- 47S. Onbulak, S. Tempelaar, R. J. Pounder, O. Gok, R. Sanyal, A. P. Dove, A. Sanyal, Macromolecules 2012, 45, 1715.
- 48S. Tempelaar, I. A. Barker, V. X. Truong, D. J. Hall, L. Mespouille, P. Dubois, A. P. Dove, Polym. Chem. 2013, 4, 174.
- 49S. Tempelaar, L. Mespouille, O. Coulembier, P. Dubois, A. P. Dove, Chem. Soc. Rev. 2013, 42, 1312.
- 50D. J. Coady, H. W. Horn, G. O. Jones, H. Sardon, A. C. Engler, R. M. Waymouth, J. E. Rice, Y. Y. Yang, J. L. Hedrick, ACS Macro Lett. 2013, 2, 306.
- 51D. P. Sanders, K. Fukushima, D. J. Coady, A. Nelson, M. Fujiwara, M. Yasumoto, J. L. Hedrick, J. Am. Chem. Soc. 2010, 132, 14724.
- 52J. M. W. Chan, H. Sardon, A. C. Engler, J. M. García, J. L. Hedrick, ACS Macro Lett. 2013, 2, 860.
- 53A. C. Engler, J. M. W. Chan, D. J. Coady, J. M. O'Brien, H. Sardon, A. Nelson, D. P. Sanders, Y. Y. Yang, J. L. Hedrick, Macromolecules 2013, 46, 1283.
- 54A. Y. Yuen, A. Bossion, A. Veloso, D. Mecerreyes, J. L. Hedrick, A. P. Dove, H. Sardon, Polym. Chem. 2018, 9, 2458.
- 55R. C. Pratt, B. G. G. Lohmeijer, D. A. Long, P. N. P. Lundberg, A. P. Dove, H. Li, C. G. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 7863.
- 56K. Makiguchi, T. Satoh, T. Kakuchi, Macromolecules 2011, 44, 1999.
- 57K. Makiguchi, S. Kikuchi, K. Yanai, Y. Ogasawara, S.-i. Sato, T. Satoh, T. Kakuchi, J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1047.
- 58D. Delcroix, B. Martín-Vaca, D. Bourissou, C. Navarro, Macromolecules 2010, 43, 8828.
- 59F. Suriano, O. Coulembier, J. L. Hedrick, P. Dubois, Polym. Chem. 2011, 2, 528.