Thiophene- and bithiophene-based π-conjugated Schiff base oligomers containing binaphthalene moieties in the backbone. Properties and computational simulations

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dc.contributor.authorGonzalez, Alexis F.
dc.contributor.authorMariman, Andrea P.
dc.contributor.authorHauyon, Rene A.
dc.contributor.authorPavez-Lizana, Danitza
dc.contributor.authorSaldias, Cesar
dc.contributor.authorSchott, Eduardo
dc.contributor.authorZarate, Ximena
dc.contributor.authorGarcia, Luis
dc.contributor.authorGonzalez-Henriquez, Carmen M.
dc.contributor.authorJessop, Ignacio A.
dc.contributor.authorTundidor-Camba, Alain
dc.contributor.authorSobarzo, Patricio A.
dc.contributor.authorTerraza, Claudio A.
dc.date.accessioned2025-01-20T17:09:58Z
dc.date.available2025-01-20T17:09:58Z
dc.date.issued2024
dc.description.abstractNew pi-conjugated Schiff base oligomers (o-AZdAN1Th and o-AZdAN2Th) based on a binaphthalene core and containing thiophene or bithiophene units in their backbone were synthesized from the reaction between [1,1 '-binaphthalene]-4,4 '-diamine with thiophene-2,5-dicarbaldehyde and [2,2 '-bithiophene]-5,5 '-dicarbaldehyde by a high-temperature polycondensation method. These new materials were slightly soluble in non-protic polar solvents, such as chloroform and dichloromethane. From GPC analysis of the CHCl3-soluble fraction, o-AZdAN1Th was found to be a tetramer, whereas o-AZdAN2Th was a trimer with 1.4 kDa and 1.3 kDa average molecular weight (Mn), respectively. Both samples exhibited high thermal stability with T5% values of 452 degrees C and 456 degrees C and relatively high Tg values of 346 degrees C and 384 degrees C, for o-AZdAN1Th and o-AZdAN2Th, respectively. The samples showed absorptions in the deep-blue (o-AZdAN1Th) and blue (o-AZdAN2Th) regions of the visible spectrum, and emission responses at 387 nm and 447 nm, respectively, with moderate Stokes shifts (77-95 nm). Their optical and electronic properties were similar to those described for thiophene-based materials, with optical bandgap values close to 2.4 eV. HOMO energy values of -5.98 and -5.95 eV and LUMO energy values of -3.87 eV and -3.84 eV were obtained for o-AZdAN1Th and o-AZdAN2Th, respectively. Theoretical DFT and TD-DFT calculations were used to compare the effect of increasing thiophene units along the backbone for the real and also theoretical o-AZdANxTh samples (x = 3 and 4 thiophene units). According to our study, these two new thiophene-based can be proposed for optoelectronic applications.
dc.description.abstractSchiff base oligomers based on a binaphthalene core were synthesized from [1,1 '-binaphthalene]-4,4 '-diamine with thiophene-2,5-dicarbaldehyde and [2,2 '-bithiophene]-5,5 '-dicarbaldehyde by a high-temperature polycondensation method.
dc.description.funderFondo Nacional de Desarrollo Cientifico y Tecnologico, FONDECYT
dc.fuente.origenWOS
dc.identifier.doi10.1039/d3py01383a
dc.identifier.eissn1759-9962
dc.identifier.issn1759-9954
dc.identifier.urihttps://doi.org/10.1039/d3py01383a
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/91079
dc.identifier.wosidWOS:001144217500001
dc.issue.numero7
dc.language.isoen
dc.pagina.final651
dc.pagina.inicio639
dc.revistaPolymer chemistry
dc.rightsacceso restringido
dc.subject.ods07 Affordable and Clean Energy
dc.subject.odspa07 Energía asequible y no contaminante
dc.titleThiophene- and bithiophene-based π-conjugated Schiff base oligomers containing binaphthalene moieties in the backbone. Properties and computational simulations
dc.typeartículo
dc.volumen15
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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