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Self-catalyzed coupling between Brønsted-acidic imidazolium salts and epoxy-based materials: a theoretical/experimental study
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SYSNO ASEP 0512147 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Self-catalyzed coupling between Brønsted-acidic imidazolium salts and epoxy-based materials: a theoretical/experimental study Author(s) Perchacz, Magdalena (UMCH-V) RID
Matějka, Libor (UMCH-V) RID
Konefal, Rafal (UMCH-V) RID, ORCID
Seixas, L. (BR)
Livi, S. (FR)
Baudoux, J. (FR)
Beneš, Hynek (UMCH-V) RID, ORCID
Donato, Ricardo Keitel (UMCH-V) ORCIDSource Title ACS Sustainable Chemistry & Engineering. - : American Chemical Society - ISSN 2168-0485
Roč. 7, č. 23 (2019), s. 19050-19061Number of pages 12 s. Language eng - English Country US - United States Keywords imidazolium salt ; ionic liquid ; epoxy Subject RIV CD - Macromolecular Chemistry OECD category Polymer science R&D Projects GA17-08273S GA ČR - Czech Science Foundation (CSF) LO1507 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support UMCH-V - RVO:61389013 UT WOS 000500650400033 EID SCOPUS 85075183404 DOI 10.1021/acssuschemeng.9b04810 Annotation Herein we present a comprehensive study on the role of Brønsted-acidic imidazolium ionic liquids (ILs) and imidazolium salts promoting the reaction between carboxyl and epoxide groups in a controlled manner at solvent-free and mild conditions. ILs were evaluated toward their ability to self-catalyze reactions between carboxyl groups and epoxy rings. Thus, an epoxy model reactant denoted phenyl glycidyl ether (PGE) was reacted with different ILs, and the reaction kinetics was followed by time-dependent FTIR spectroscopy. The resulting products were characterized by 1H NMR and MALDI-TOF, which also allowed a comprehensive investigation of the reaction mechanism by following the reaction intermediates formation. The detected intermediates were then evaluated by density functional theory (DFT) simulations to calculate their energy profiles, revealing the preferred mechanism pathways. These mono-, bi-, and tetra-functionalized ILs (with carboxyl groups) acted as all-in-one reaction systems for materials synthesis or modification, with the potential of producing a broad range of epoxy based materials via metal catalyst-free coupling reactions. Workplace Institute of Macromolecular Chemistry Contact Eva Čechová, cechova@imc.cas.cz ; Tel.: 296 809 358 Year of Publishing 2020 Electronic address https://pubs.acs.org/doi/10.1021/acssuschemeng.9b04810
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