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Crystal structure determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with selected properties of imine in neutral and protonated form with camforosulphonic acid: theoretical and experimental studies

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dc.abstract.enThe crystal structure was determined for the first time for 4-[(di-p-tolyl-amino)benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine (trans-PPL9) by X-ray diffraction. The imine crystallized in the monoclinic P21/n space group with a = 18.9567(7) Å, b = 6.18597(17) Å, c = 22.5897(7) Å, and β = 114.009(4)°. Intermolecular interactions in the PPL9 crystal were only weak C−H⋯N hydrogen bonds investigated using the Hirshfeld surface. The electronic and geometric structure of the imine were investigated by the density functional theory and the time-dependent density-functional theory. The properties of the imine in neutral and protonated form with camforosulphonic acid (CSA) were investigated using cyclic voltammetry, UV–vis and 1H NMR spectroscopy. Theoretical and experimental studies showed that for the 1:1 molar ratio the protonation occured on nitrogen in pyridine in the PPL9 structure, as an effect of Brönsted acid–base interactions. Thermographic camera was used to defined defects in constructed simple devices with ITO/PPL9 (or PPL9:CSA)/Ag/ITO architecture. In conclusion, a thermally stable imine was synthesized in crystalline form and by CSA doping, a modification of absorption spectra together with reduction of overheating process was observed, suggesting its potential application in optoelectronics.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorIWAN, Agnieszka
dc.contributor.authorBOGDANOWICZ, Krzysztof
dc.contributor.authorPRZYBYŁ, WOJCIECH
dc.contributor.authorDYLONG, Agnieszka
dc.contributor.authorKonieczny, Krzysztof A.
dc.contributor.authorDYSZ, Karolina
dc.contributor.authorTUROWSKA-TYRK, ILONA
dc.contributor.authorKONIECZNY, KRZYSZTOF
dc.contributor.authorKaim, Andrzej
dc.date.accessioned2024-01-24T20:55:51Z
dc.date.available2024-01-24T20:55:51Z
dc.date.copyright2021-04-13
dc.date.issued2021
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number8
dc.description.versionFINAL_PUBLISHED
dc.description.volume14
dc.identifier.doi10.3390/MA14081952
dc.identifier.issn1996-1944
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/103996
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofMaterials
dc.relation.pages1952
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enimines
dc.subject.enazomethines
dc.subject.encrystal structure
dc.subject.ennon-covalent interactions
dc.subject.encamforosulphonic acid
dc.subject.enthermographic camera
dc.subject.enprotonation
dc.titleCrystal structure determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with selected properties of imine in neutral and protonated form with camforosulphonic acid: theoretical and experimental studies
dc.typeJournalArticle
dspace.entity.typePublication