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A copper-amidocarboxylate based metal organic macrocycle and framework: synthesis, structure and catalytic activities towards microwave assisted alcohol oxidation and Knoevenagel reactions

2019-07-07Journal article Restricted access
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dc.contributor.authorKarmakar, Anirban
dc.contributor.authorSoliman, Mohamed Mostafa Aboelhassan
dc.contributor.authorAlegria, Elisabete
dc.contributor.authorRubio, Guilherme
dc.contributor.authorGuedes Da Silva, M. Fátima C.
dc.contributor.authorPombeiro, Armando
dc.date.accessioned2019-07-19T10:47:30Z
dc.date.available2019-07-19T10:47:30Z
dc.date.issued2019-07-07
dc.description.abstractReactions of 3,3 '-{(pyridine-2,6-dicarbonyl)bis(azanediyl)}dibenzoic acid (H2L) with copper(ii) nitrate were studied and the obtained compounds [Cu-2(1:2 kappa(OO2)-O-1,2:3 kappa(OO4)-O-3-L)(mu-NO3)(mu(3)-OH)(MeOH)(2)](2)center dot 2MeOH center dot 1DMF (1) and [Cu(mu-1 kappa O-1:2 kappa O-2,3 kappa O-3:4 kappa O-4-L)(DMF)](n)center dot 4n(DMF) (2) were characterized by elemental analysis, FT-IR spectroscopy, and single-crystal and powder X-ray diffraction. Compound 1 is a macrocyclic tetranuclear Cu(ii) complex possessing a central, quasi-planar rhomboid shaped {Cu-4} cluster, which is the first example of a Cu(ii) based macrocyclic tetranuclear complex using such a linker. Compound 2 is a 2D metal organic framework having dinuclear paddlewheel type Cu(ii) assemblies that act as secondary building blocks. The topological analysis of framework 2 revealed that it has a 2,4-connected binodal net. Both compounds act as heterogeneous, easily recovered and reusable catalysts (the catalysts could be reused at least four times without significant loss of activity) for the microwave-assisted oxidation of several alcohols, as well as for the Knoevenagel condensation reaction of various aldehydes. The effect of reaction parameters such as temperature, time and type of oxidant was investigated. This study demonstrates that compound 1 can act as an efficient catalyst for the conversion of secondary alcohols (1-phenylethanol) to the corresponding ketones with high selectivity and yields up to 93% after 1 h of reaction at 120 degrees C and using t-BuOOH as an oxidant. Moreover, these compounds effectively catalyze the Knoevenagel condensation reactions of aldehydes with malononitrile and produce reaction yields between 64 and 99% within a very short period (10 min) under low power microwave irradiation. Furthermore, we have also studied the effectiveness of our catalyst 1 towards peroxidative oxidation/Knoevenagel condensation cascade reactions under microwave conditions.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationKARMAKAR, Anirban; [et al] – A copper-amidocarboxylate based metal organic macrocycle and framework: synthesis, structure and catalytic activities towards microwave assisted alcohol oxidation and Knoevenagel reactions. New Journal of Chemistry. ISSN 1144-0546. Vol. 43, N.º 25 (2019), pp. 9843-9854pt_PT
dc.identifier.doi10.1039/c9nj02064kpt_PT
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.urihttp://hdl.handle.net/10400.21/10339
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherRoyal Society of Chemistrypt_PT
dc.relationUID/QUI/00100/2019 - FCTpt_PT
dc.relationPTDC/QEQ-QIN/3967/2014 - FCTpt_PT
dc.relationPTDC/QUI-QIN/29778/2017 - FCTpt_PT
dc.relationSYNTHESIS OF NANOPOROUS HOMOCHIRAL METAL-ORGANIC FRAMEWORKS AND THEIR APPLICATION IN ENANTIOSELECTIVE CATALYSIS
dc.relation.publisherversionhttps://pubs.rsc.org/en/content/articlepdf/2019/nj/c9nj02064kpt_PT
dc.subjectCopper-amidocarboxylatept_PT
dc.subjectMetal organic macrocyclept_PT
dc.subjectKnoevenagel reactionspt_PT
dc.titleA copper-amidocarboxylate based metal organic macrocycle and framework: synthesis, structure and catalytic activities towards microwave assisted alcohol oxidation and Knoevenagel reactionspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleSYNTHESIS OF NANOPOROUS HOMOCHIRAL METAL-ORGANIC FRAMEWORKS AND THEIR APPLICATION IN ENANTIOSELECTIVE CATALYSIS
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F76192%2F2011/PT
oaire.citation.endPage9854pt_PT
oaire.citation.issue25pt_PT
oaire.citation.startPage9843pt_PT
oaire.citation.titleNew Journal of Chemistrypt_PT
oaire.citation.volume43pt_PT
person.familyNameKarmakar
person.familyNameSoliman
person.familyNameAlegria
person.familyNameRúbio
person.familyNameGuedes da Silva
person.familyNamePombeiro
person.givenNameAnirban
person.givenNameMohamed Mostafa Aboelhassan
person.givenNameElisabete
person.givenNameGuilherme
person.givenNameM. Fátima C.
person.givenNameArmando
person.identifier863202
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person.identifier.ciencia-id8311-38FA-CEFB
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person.identifier.orcid0000-0003-4060-1057
person.identifier.orcid0000-0002-6889-0703
person.identifier.orcid0000-0003-4836-2409
person.identifier.orcid0000-0001-8323-888X
person.identifier.ridG-3990-2012
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person.identifier.scopus-author-id14037235600
person.identifier.scopus-author-id8315848300
person.identifier.scopus-author-id6701761571
person.identifier.scopus-author-id7006067269
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
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