Synthesis and characterization of aromatic compounds containing imine and amine groups via oxidative polycondensation

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dc.authoridKaya, Ismet/0000-0002-9813-2962
dc.contributor.authorSenol, Dilek
dc.contributor.authorKaya, İsmet
dc.date.accessioned2025-01-27T20:48:01Z
dc.date.available2025-01-27T20:48:01Z
dc.date.issued2014
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractIn this study, Schiff bases compounds were synthesized from the condensation of 3,5-diaminobenzoic acid and 4,4-diaminobenzanilit with salicylaldehyde, o-vanillin, 4-hydroxy benzaldehyde, and 2-hydroxy-l-naphthaldehyde. The derived monomers were changed into their polyphenol species by oxidative polycondensation in aqueous alkaline medium by using NaOCl as the oxidant. At the optimum reaction conditions, the yield of 3,5-bis((2-hydroxynaphthalen-1-yl)metyleneamino) benzoic acid was 69%. The structures of the monomers and polymers were confirmed by FTIR, ultraviolet-visible (UV-vis), H-1-NMR, and C-13-NMR analyses. The H-1-NMR and C-13-NMR data showed that polymerization preceded by C-C and C-O couplings of the monomer units (phenylene and oxyphenylene groups). The molecular weight distribution of the product was determined by size exclusion chromatography. The number-average molecular weight (M-n), weight-average molecular weight (M-w), and polydispersity index of P-4,4-DABAVA were 20,970, 15,420gmol(-1), and 1.36 for NaOCl oxidant, respectively. The CV behaviors electrochemical HOMO, LUMO, and energy gaps (E-g) were investigated using glassy carbon electrode as the working electrode. Optical E-g band gaps were made UV-vis measurements. Solid-state electrical conductivities of both doped and undoped states of the synthesized polyphenols were evaluated showing that conductivity of P-3,5-DABAHNA is better than other polymers. Optical properties were investigated by UV-vis and fluorescence analyses. Maximum fluorescence intensity was obtained from the solution of P-3,5-DABAVA.
dc.identifier.doi10.1080/15685551.2013.876754
dc.identifier.endpage575
dc.identifier.issn1385-772X
dc.identifier.issn1568-5551
dc.identifier.issue6
dc.identifier.scopus2-s2.0-84899456756
dc.identifier.scopusqualityQ3
dc.identifier.startpage557
dc.identifier.urihttps://doi.org/10.1080/15685551.2013.876754
dc.identifier.urihttps://hdl.handle.net/20.500.12428/25113
dc.identifier.volume17
dc.identifier.wosWOS:000334333500005
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTaylor & Francis Ltd
dc.relation.ispartofDesigned Monomers and Polymers
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectSchiff base polymers
dc.subjectpolyphenols
dc.subjectoxidative polycondensation
dc.subjectoptimum reaction conditions
dc.titleSynthesis and characterization of aromatic compounds containing imine and amine groups via oxidative polycondensation
dc.typeArticle

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