Architectural Control of Isosorbide-Based Polyethers via Ring-Opening Polymerization

Derek J. Saxon, Mohammadreza Nasiri, Mukunda Mandal, Saurabh Maduskar, Paul J. Dauenhauer, Christopher J. Cramer, Anne M. Lapointe, Theresa M. Reineke

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Isosorbide is a rigid, sugar-derived building block that has shown promise in high-performance materials, albeit with a lack of available controlled polymerization methods. To this end, we provide mechanistic insights into the cationic and quasi-zwitterionic ring-opening polymerization (ROP) of an annulated isosorbide derivative (1,4:2,5:3,6-trianhydro-d-mannitol, 5). Ring-opening selectivity of this tricyclic ether was achieved, and the polymerization is selectively directed toward different macromolecular architectures, allowing for formation of either linear or cyclic polymers. Notably, straightforward recycling of unreacted monomer can be accomplished via sublimation. This work provides the first platform for tailored polymer architectures from isosorbide via ROP.

Original languageEnglish (US)
Pages (from-to)5107-5111
Number of pages5
JournalJournal of the American Chemical Society
Volume141
Issue number13
DOIs
StatePublished - Apr 3 2019

Bibliographical note

Funding Information:
This work was supported by the National Science Foundation under the Center for Sustainable Polymers (CHE-1413862). Mass spectrometry analysis was performed at The University of Minnesota Department of Chemistry Mass Spectrometry Laboratory (MSL), supported by the Office of the Vice President of Research, College of Science and Engineering, and the Department of Chemistry at the University of Minnesota, as well as The National Science Foundation (NSF, Award CHE-1336940). The authors acknowledge the Minnesota Supercomputing Institute (MSI) at the University of Minnesota for providing resources that contributed to the research results reported within this paper. This work also made use of the NMR facility at Cornell University which is supported, in part, by the National Science Foundation (CHE-1531632).

Funding Information:
This work was supported by the National Science Foundation under the Center for Sustainable Polymers (CHE-1413862). Mass spectrometry analysis was performed at The University of Minnesota Department of Chemistry Mass Spectrometry Laboratory (MSL), supported by the Office of the Vice President of Research, College of Science and Engineering, and the Department of Chemistry at the University of Minnesota, as well as The National Science Foundation (NSF, Award CHE-1336940). The authors acknowledge the Minnesota Supercomputing Institute (MSI) at the University of Minnesota for providing resources that contributed to the research results reported within this paper. This work also made use of the NMR facility at Cornell University, which is supported, in part, by the National Science Foundation (CHE-1531632). The authors acknowledge Dr. Leon Lillie for helpful discussions.

Publisher Copyright:
© 2019 American Chemical Society.

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