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Synthesis and structure of copper complexes of a N6O4 macrocyclic ligand and catalytic application in alcohol oxidation

2019-05-07Journal article Restricted access
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dc.contributor.authorMa, Zhen
dc.contributor.authorWang, Qijun
dc.contributor.authorAlegria, Elisabete
dc.contributor.authorGuedes Da Silva, M. Fátima C.
dc.contributor.authorMartins, Luisa
dc.contributor.authorJ. P. Telo, João P. Telo, João Paulo Telo
dc.contributor.authorCorreia, Isabel
dc.contributor.authorPombeiro, Armando
dc.date.accessioned2019-07-22T13:50:06Z
dc.date.available2019-07-22T13:50:06Z
dc.date.issued2019-05-07
dc.description.abstractReactions between N6O4 macrocyclic 1,4,19,22,25,40-hexaaza-10,13,31,34-tetraoxa-6,14,27,35(1,4)-tetrabenzenacyclopentacontane (L) and several copper salts (viz. trifuoromethane and toluene sulfonates, nitrate, perchlorate, benzoate, and acetate) led to the formation of dinuclear compounds [Cu-2(OSO2CF3)(2)(DMF)(2)L](SO3CF3)(2) (1), [Cu-2(p-OSO2C6H4Me)(2)L(DMF)(2)](SO3C6H4Me)(2) (2), [Cu-2(ONO2)(2)L(DMF)(2)](NO3)(2) (3), [Cu-2(OClO3)(2)(DMF)(2)L](ClO4)(2) (4), [Cu-2(OOCPh)(2)L(H2O)(2)](O2CPh)(2) (5), and [Cu-2(OOCMe)(4)L] (6), which were characterized by IR, elemental analysis and TG-DTA (thermogravimetric-differential thermal analysis), as well as by single-crystal X-ray diffraction, EPR (electron paramagnetic resonance) spectroscopy, and electrochemical techniques (cyclic voltammetry and controlled potential electrolysis). The molecular structures of compounds 1-6 reveal a considerable conformational flexibility of the ligand L, which allowed its readjustment for the formation of the metal compounds and confirmed the presence of dinuclear endo macrocyclic species. In every case, the L ligand coordinates to each copper cation via three nitrogen atoms, with the remaining coordination positions of the metal square pyramid environment being accomplished by neutral or anionic ligands. The macrocyclic cavities appear to be adequate for the enclosure of a neutral species as proved by compound 6 with 1,4-dioxane. The compounds, in combination with the TEMPO (2,2,6,6-tetramethyl-piperidinyloxyl) radical and in alkaline aqueous solution, act as efficient catalysts in the aerobic oxidation of different alcohols to the corresponding aldehydes (yields up to 99% and TON up 232) after 20 h at 70 degrees C. In addition, the microwave-assisted solvent-free peroxidative oxidation (by tert-butylhydroperoxide, TBHP) of 1-phenylethanol led to acetophenone yields up to 99% and TOF of 1.1 x 10(3) after 0.5 h, without any additive.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationMA, Zhen; [et al] – Synthesis and structure of copper complexes of a N6O4 macrocyclic ligand and catalytic application in alcohol oxidation. Catalysts. ISSN 2073-4344. Vol. 9, N.º 5 (2019), pp. 1-23pt_PT
dc.identifier.doi10.3390/catal9050424pt_PT
dc.identifier.issn2073-4344
dc.identifier.urihttp://hdl.handle.net/10400.21/10351
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relation21261002 - Science Foundation of Chinapt_PT
dc.relationUID/QUI/00100/2019 - FCTpt_PT
dc.relationPTDC/QEQ-QIN/3967/2014 - FCTpt_PT
dc.relationSYNTHESIS, ELECTROCHEMICAL AND LUMINESCENT BEHAVIOURS OF POLYAZA-COMPLEXES
dc.subjectMacrocyclicpt_PT
dc.subjectCopper complexespt_PT
dc.subjectCatalysispt_PT
dc.subjectAlcohol oxidationpt_PT
dc.titleSynthesis and structure of copper complexes of a N6O4 macrocyclic ligand and catalytic application in alcohol oxidationpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleSYNTHESIS, ELECTROCHEMICAL AND LUMINESCENT BEHAVIOURS OF POLYAZA-COMPLEXES
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F24691%2F2005/PT
oaire.citation.endPage23pt_PT
oaire.citation.issue5pt_PT
oaire.citation.startPage1pt_PT
oaire.citation.titleCatalystspt_PT
oaire.citation.volume9pt_PT
person.familyNameAlegria
person.familyNameGuedes da Silva
person.familyNameMartins
person.familyNameTelo
person.familyNameCorreia
person.familyNamePombeiro
person.givenNameElisabete
person.givenNameM. Fátima C.
person.givenNameLuisa
person.givenNameJoão
person.givenNameIsabel
person.givenNameArmando
person.identifier863202
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person.identifier.ciencia-idA51A-5072-8FE7
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person.identifier.ciencia-id8311-38FA-CEFB
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person.identifier.ridE-9945-2012
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person.identifier.scopus-author-id6603591261
person.identifier.scopus-author-id7003557498
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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