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Conventional vs. microwave- or mechanically-assisted synthesis of dihomooxacalix[4]arene phthalimides: NMR, X-ray and photophysical analysis

2021-03Journal article Open access
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dc.contributor.authorSantos Miranda, Alexandre
dc.contributor.authorMarcos, Paula M.
dc.contributor.authorJ.R., Ascenso
dc.contributor.authorRobalo, M. Paula
dc.contributor.authorBonifácio, Vasco D. B.
dc.contributor.authorBerberan-Santos, Mario
dc.contributor.authorHickey, Neal
dc.contributor.authorGeremia, Silvano
dc.date.accessioned2021-05-27T10:02:55Z
dc.date.available2021-05-27T10:02:55Z
dc.date.issued2021-03
dc.description.abstractDirect O-alkylation of p-tert-butyldihomooxacalix[4]arene (1) with N-(bromopropyl)- or N-(bromoethyl)phthalimides and K2CO3 in acetonitrile was conducted under conventional heating (reflux) and using microwave irradiation and ball milling methodologies. The reactions afforded mono- and mainly distal di-substituted derivatives in the cone conformation, in a total of eight compounds. They were isolated by column chromatography, and their conformations and the substitution patterns were established by NMR spectroscopy (H-1, C-13, COSY and NOESY experiments). The X-ray structures of four dihomooxacalix[4]arene phthalimide derivatives (2a, 3a, 3b and 5a) are reported, as well as their photophysical properties. The microwave (MW)-assisted alkylations drastically reduced the reaction times (from days to less than 45 min) and produced higher yields of both 1,3-di-substituted phthalimides (3a and 6a) with higher selectivity. Ball milling did not reveal to be a good method for this kind of reaction.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationMIRANDA, Alexandre S.; [et al] – Conventional vs. microwave- or mechanically-assisted synthesis of dihomooxacalix[4]arene phthalimides: NMR, X-ray and photophysical analysis. Molecules. eISSN 1420-3049. Vol. 26, N.º 6 (2021), pp. 1-19pt_PT
dc.identifier.doi10.3390/molecules26061503pt_PT
dc.identifier.eissn1420-3049
dc.identifier.urihttp://hdl.handle.net/10400.21/13385
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationUIDB/00100/2020 - FCT European Commissionpt_PT
dc.relationUIDB/04565/2020 - FCT European Commissionpt_PT
dc.relationPTDC/MEC-ONC/29327/2017 - FCT European Commissionpt_PT
dc.relationSFRH/BD/129323/2017 - FCT European Commissionpt_PT
dc.subjectDihomooxacalix[4]arenespt_PT
dc.subjectPhthalimide derivativespt_PT
dc.subjectConventional synthesispt_PT
dc.subjectMicrowave irradiationpt_PT
dc.subjectBall millingpt_PT
dc.subjectNMR spectroscopypt_PT
dc.subjectX-ray diffractionpt_PT
dc.subjectElectronic absorptionpt_PT
dc.subjectFluorescence studiespt_PT
dc.titleConventional vs. microwave- or mechanically-assisted synthesis of dihomooxacalix[4]arene phthalimides: NMR, X-ray and photophysical analysispt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage19pt_PT
oaire.citation.issue6pt_PT
oaire.citation.startPage1pt_PT
oaire.citation.titleMoleculespt_PT
oaire.citation.volume26pt_PT
person.familyNameSantos Miranda
person.familyNameMarcos
person.familyNameAscenso
person.familyNameRobalo
person.familyNameBonifácio
person.familyNameBerberan-Santos
person.familyNameHickey
person.familyNameGeremia
person.givenNameAlexandre
person.givenNamePaula Maria
person.givenNameJose
person.givenNameMaria Paula
person.givenNameVasco
person.givenNameMario
person.givenNameNeal
person.givenNameSilvano
person.identifier385575
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person.identifier.orcid0000-0003-1271-5719
person.identifier.orcid0000-0002-0711-5113
person.identifier.ridP-7388-2015
person.identifier.ridB-2002-2012
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rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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