Self-Catalyzed Coupling between Brønsted-Acidic Imidazolium Salts and Epoxy-Based Materials: A Theoretical/Experimental Study

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dc.contributor.authorPerchacz M.
dc.contributor.authorMatejka L.
dc.contributor.authorKonefal R.
dc.contributor.authorSeixas L.
dc.contributor.authorLivi S.
dc.contributor.authorBaudoux J.
dc.contributor.authorBenes H.
dc.contributor.authorDonato R.K.
dc.date.accessioned2024-03-12T23:50:51Z
dc.date.available2024-03-12T23:50:51Z
dc.date.issued2019
dc.description.abstractCopyright © 2019 American Chemical Society.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.
dc.description.firstpage19050
dc.description.issuenumber23
dc.description.lastpage19061
dc.description.volume7
dc.identifier.doi10.1021/acssuschemeng.9b04810
dc.identifier.issn2168-0485
dc.identifier.urihttps://dspace.mackenzie.br/handle/10899/35143
dc.relation.ispartofACS Sustainable Chemistry and Engineering
dc.rightsAcesso Restrito
dc.subject.otherlanguageCatalysis
dc.subject.otherlanguageIonic liquid
dc.subject.otherlanguageMechanism
dc.subject.otherlanguageOne-pot reaction
dc.subject.otherlanguageRing-opening
dc.subject.otherlanguageSolvent-free
dc.titleSelf-Catalyzed Coupling between Brønsted-Acidic Imidazolium Salts and Epoxy-Based Materials: A Theoretical/Experimental Study
dc.typeArtigo
local.scopus.citations5
local.scopus.eid2-s2.0-85075183404
local.scopus.subjectFTIR spectroscopy
local.scopus.subjectImidazolium ionic liquids
local.scopus.subjectMaterials synthesis
local.scopus.subjectOne-pot reaction
local.scopus.subjectPhenyl glycidyl ethers
local.scopus.subjectReaction mechanism
local.scopus.subjectRing opening
local.scopus.subjectSolvent free
local.scopus.updated2024-05-01
local.scopus.urlhttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85075183404&origin=inward
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