Inverse Vulcanization of Activated Norbornenyl Esters-A Versatile Platform for Functional Sulfur Polymers.

Autor: Grimm AP; Institute for Biological Interfaces III (IBG-3) Soft Matter Synthesis Laboratory, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany., Plank M; Institute of Functional Interfaces (IFG) Soft Matter Synthesis Laboratory, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany., Stihl A; Institute of Organic Chemistry and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena (FSU), Lessingstraße 8, 07743, Jena, Germany.; Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena (FSU), Philosophenweg 7, 07743, Jena, Germany., Schmitt CW; Institute for Biological Interfaces III (IBG-3) Soft Matter Synthesis Laboratory, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany., Voll D; Institute for Technical Chemistry and Polymer Chemistry (ITCP), Karlsruhe Institute of Technology (KIT), Engesserstraße 18, 76131, Karlsruhe, Germany., Schacher FH; Institute of Organic Chemistry and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena (FSU), Lessingstraße 8, 07743, Jena, Germany.; Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena (FSU), Philosophenweg 7, 07743, Jena, Germany.; Helmholtz Institute for Polymers in Energy Applications Jena (HIPOLE Jena), Lessingstraße 12-14, 07743, Jena, Germany., Lahann J; Institute of Functional Interfaces (IFG) Soft Matter Synthesis Laboratory, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.; Biointerfaces Institute, University of Michigan, 2800 Plymouth Road, Ann Arbor, MI 48109, USA., Théato P; Institute for Biological Interfaces III (IBG-3) Soft Matter Synthesis Laboratory, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.; Institute for Technical Chemistry and Polymer Chemistry (ITCP), Karlsruhe Institute of Technology (KIT), Engesserstraße 18, 76131, Karlsruhe, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Sep 02; Vol. 63 (36), pp. e202411010. Date of Electronic Publication: 2024 Aug 02.
DOI: 10.1002/anie.202411010
Abstrakt: Elemental sulfur has shown to be a promising alternative feedstock for development of novel polymeric materials with high sulfur content. However, the utilization of inverse vulcanized polymers is restricted by the limitation of functional comonomers suitable for an inverse vulcanization. Control over properties and structure of inverse vulcanized polymers still poses a challenge to current research due to the dynamic nature of sulfur-sulfur bonds and high temperature of inverse vulcanization reactions. In here, we report for the first time the inverse vulcanization of norbornenyl pentafluorophenyl ester (NB-PFPE), allowing for post-modification of inverse vulcanized polymers via amidation of reactive PFP esters to yield high sulfur content polymers under mild conditions. Amidation of the precursor material with three functional primary amines (α-amino-ω-methoxy polyethylene glycol, aminopropyl trimethoxy silane, allylamine) was investigated. The resulting materials were applicable as sulfur containing poly(ethylene glycol) nanoparticles in aqueous environment. Cross-linked mercury adsorbents, sulfur surface coatings, and high-sulfur content networks with predictable thermal properties were achievable using aminopropyl trimethoxy silane and allylamine for post-polymerization modification, respectively. With the broad range of different amines available and applicable for post-polymerization modification, the versatility of poly(sulfur-random-NB-PFPE) as a platform precursor polymer for novel specialized sulfur containing materials was showcased.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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