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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 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Self-catalyzed coupling between Brønsted-acidic imidazolium salts and epoxy-based materials: a theoretical/experimental study Tvůrce(i) 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) ORCIDZdroj.dok. ACS Sustainable Chemistry & Engineering. - : American Chemical Society - ISSN 2168-0485
Roč. 7, č. 23 (2019), s. 19050-19061Poč.str. 12 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova imidazolium salt ; ionic liquid ; epoxy Vědní obor RIV CD - Makromolekulární chemie Obor OECD Polymer science CEP GA17-08273S GA ČR - Grantová agentura ČR LO1507 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Způsob publikování Omezený přístup Institucionální podpora UMCH-V - RVO:61389013 UT WOS 000500650400033 EID SCOPUS 85075183404 DOI 10.1021/acssuschemeng.9b04810 Anotace 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. Pracoviště Ústav makromolekulární chemie Kontakt Eva Čechová, cechova@imc.cas.cz ; Tel.: 296 809 358 Rok sběru 2020 Elektronická adresa https://pubs.acs.org/doi/10.1021/acssuschemeng.9b04810
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