Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10773/37535 |
Resumo: | The hexadentate ligand, 2,2′-bis(salicylideneamino)azobenzene, 1 has been synthesized from 2,2′-diaminoazobenzene and salicylaldehyde in refluxing diethyl ether. Reaction of ligand 1 with Cu(II) acetate and Cu(II) perchlorate separately in methanol afforded tetradentate (N,N,N,O) Cu(II) complexes, Cu(L) & [Cu(HL)]ClO4 respectively [where H2L represent the one imine moiety cleavage product of ligand 1 (H represents the dissociable amino and phenolic protons)]. These were characterized by microanalytical data and spectroscopic studies. In addition, the crystal structures of the ligand 1 and complexes Cu(L) & [Cu(HL)]ClO4 were determined by X-ray diffraction analysis. The diffraction analysis revealed that the ligand (H2L) binds Cu(II) centers in (N,N,N,O) tetra dentate fashion in distorted square planer geometry. In complex [Cu(HL)]ClO4 the apical position of copper center is weakly coordinated with one perchlorate ion. The dimeric structure of the molecule [Cu(HL)]ClO4 is stabilized through NH2···O hydrogen bonds. The fluorescence and redox property of ligand 1 and complexes Cu(L) & [Cu(HL)]ClO4 were studied. Preliminary DFT calculations were carried out using crystallographic coordinates to understand the electronic spectra and redox properties of the ligand and complexes. The complex Cu(L) shows very good catalytic activities towards oxidation of benzyl alcohol to benzaldeyhde (under solvent-free condition) and organic thioethers to sulfoxide and sulfones using H2O2 as the oxidant. |
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Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexesCopper(II)C=N bond cleavageCrystal structuresRedoxEmissionOxidation reactionsThe hexadentate ligand, 2,2′-bis(salicylideneamino)azobenzene, 1 has been synthesized from 2,2′-diaminoazobenzene and salicylaldehyde in refluxing diethyl ether. Reaction of ligand 1 with Cu(II) acetate and Cu(II) perchlorate separately in methanol afforded tetradentate (N,N,N,O) Cu(II) complexes, Cu(L) & [Cu(HL)]ClO4 respectively [where H2L represent the one imine moiety cleavage product of ligand 1 (H represents the dissociable amino and phenolic protons)]. These were characterized by microanalytical data and spectroscopic studies. In addition, the crystal structures of the ligand 1 and complexes Cu(L) & [Cu(HL)]ClO4 were determined by X-ray diffraction analysis. The diffraction analysis revealed that the ligand (H2L) binds Cu(II) centers in (N,N,N,O) tetra dentate fashion in distorted square planer geometry. In complex [Cu(HL)]ClO4 the apical position of copper center is weakly coordinated with one perchlorate ion. The dimeric structure of the molecule [Cu(HL)]ClO4 is stabilized through NH2···O hydrogen bonds. The fluorescence and redox property of ligand 1 and complexes Cu(L) & [Cu(HL)]ClO4 were studied. Preliminary DFT calculations were carried out using crystallographic coordinates to understand the electronic spectra and redox properties of the ligand and complexes. The complex Cu(L) shows very good catalytic activities towards oxidation of benzyl alcohol to benzaldeyhde (under solvent-free condition) and organic thioethers to sulfoxide and sulfones using H2O2 as the oxidant.Elsevier2023-05-05T11:01:36Z2018-07-01T00:00:00Z2018-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/37535eng0020-169310.1016/j.ica.2018.04.042Pratihar, Jahar LalMandal, ParitoshBrandão, PaulaMal, DasarathFélix, Vítorinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-02-22T12:12:35Zoai:ria.ua.pt:10773/37535Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:08:09.450182Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes |
title |
Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes |
spellingShingle |
Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes Pratihar, Jahar Lal Copper(II) C=N bond cleavage Crystal structures Redox Emission Oxidation reactions |
title_short |
Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes |
title_full |
Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes |
title_fullStr |
Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes |
title_full_unstemmed |
Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes |
title_sort |
Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes |
author |
Pratihar, Jahar Lal |
author_facet |
Pratihar, Jahar Lal Mandal, Paritosh Brandão, Paula Mal, Dasarath Félix, Vítor |
author_role |
author |
author2 |
Mandal, Paritosh Brandão, Paula Mal, Dasarath Félix, Vítor |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Pratihar, Jahar Lal Mandal, Paritosh Brandão, Paula Mal, Dasarath Félix, Vítor |
dc.subject.por.fl_str_mv |
Copper(II) C=N bond cleavage Crystal structures Redox Emission Oxidation reactions |
topic |
Copper(II) C=N bond cleavage Crystal structures Redox Emission Oxidation reactions |
description |
The hexadentate ligand, 2,2′-bis(salicylideneamino)azobenzene, 1 has been synthesized from 2,2′-diaminoazobenzene and salicylaldehyde in refluxing diethyl ether. Reaction of ligand 1 with Cu(II) acetate and Cu(II) perchlorate separately in methanol afforded tetradentate (N,N,N,O) Cu(II) complexes, Cu(L) & [Cu(HL)]ClO4 respectively [where H2L represent the one imine moiety cleavage product of ligand 1 (H represents the dissociable amino and phenolic protons)]. These were characterized by microanalytical data and spectroscopic studies. In addition, the crystal structures of the ligand 1 and complexes Cu(L) & [Cu(HL)]ClO4 were determined by X-ray diffraction analysis. The diffraction analysis revealed that the ligand (H2L) binds Cu(II) centers in (N,N,N,O) tetra dentate fashion in distorted square planer geometry. In complex [Cu(HL)]ClO4 the apical position of copper center is weakly coordinated with one perchlorate ion. The dimeric structure of the molecule [Cu(HL)]ClO4 is stabilized through NH2···O hydrogen bonds. The fluorescence and redox property of ligand 1 and complexes Cu(L) & [Cu(HL)]ClO4 were studied. Preliminary DFT calculations were carried out using crystallographic coordinates to understand the electronic spectra and redox properties of the ligand and complexes. The complex Cu(L) shows very good catalytic activities towards oxidation of benzyl alcohol to benzaldeyhde (under solvent-free condition) and organic thioethers to sulfoxide and sulfones using H2O2 as the oxidant. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-07-01T00:00:00Z 2018-07-01 2023-05-05T11:01:36Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10773/37535 |
url |
http://hdl.handle.net/10773/37535 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
0020-1693 10.1016/j.ica.2018.04.042 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
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1799137735115538432 |