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Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization

Nistanaki, Sepand K. and Nelson, Hosea M. (2020) Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization. ACS Macro Letters, 9 (5). pp. 731-735. ISSN 2161-1653. PMCID PMC8297915. doi:10.1021/acsmacrolett.0c00227.

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We report the utility of readily available heterocycles as precursors to unique ring-opening metathesis polymerization (ROMP) monomers. Photochemical valence isomerization reactions of pyridones, dihydropyridines, and pyrones dearomatize the parent heterocycles to their highly strained Dewar isomers, which readily engage in controlled ROMP reactions using Grubbs catalysts. This strategy is used to access polymer backbones that contain strained β-lactam and azetidine cores, which can be further derivatized using postpolymerization chemistries. We demonstrate this through the synthesis of water-soluble β-amino acid polymers that have potential applications as biomedical materials, along with the synthesis of highly soluble poly(acetylene) derivatives, which have potential applications as organic conductive materials derived from biofeedstock chemicals.

Item Type:Article
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URLURL TypeDescription CentralArticle Paper
Nistanaki, Sepand K.0000-0002-5252-803X
Nelson, Hosea M.0000-0002-4666-2793
Additional Information:© 2020 American Chemical Society. Received 23 March 2020. Accepted 23 April 2020. Published online 1 May 2020. Published in issue 19 May 2020. We thank the David and Lucile Packard Foundation (to H.M.N.), Pew Charitable Trusts (to H.M.N.), and the Alfred P. Sloan Foundation (to H.M.N.) for generous support. S.K.N. acknowledges the USPHS National Research Service Award (T32GM008496). We thank Heather D. Maynard, Douglas Rose, Garret M. Miyake, and Daniel A. Estabrook for useful discussions. We thank Ignacio B. Martini and the UCLA Molecular Instrumentation Center for help and access to GPC instrumentation. We also thank Craig J. Hawker, Allison Abdilla, and the Materials Research Laboratory at UCSB for help with GPC experiments. The authors declare no competing financial interest.
Funding AgencyGrant Number
David and Lucile Packard FoundationUNSPECIFIED
Pew Charitable TrustUNSPECIFIED
Alfred P. Sloan FoundationUNSPECIFIED
NIH Predoctoral FellowshipT32GM008496
Subject Keywords:Monomers, Polymerization, Heterocyclic compounds, Catalysts, Polymers
Issue or Number:5
PubMed Central ID:PMC8297915
Record Number:CaltechAUTHORS:20210811-225351442
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Official Citation:Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization Sepand K. Nistanaki and Hosea M. Nelson ACS Macro Letters 2020 9 (5), 731-735 DOI: 10.1021/acsmacrolett.0c00227
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:110212
Deposited By: George Porter
Deposited On:12 Aug 2021 19:32
Last Modified:16 Aug 2021 21:42

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