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

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dc.catalogadorpva
dc.contributor.authorGonzález Guzmán, Alexis Fabián
dc.contributor.authorMariman Marchant, Andrea Paz
dc.contributor.authorHauyón Sepúlveda, René Alejandro
dc.contributor.authorPavéz Lizana, Danitza Belén
dc.contributor.authorSaldías Barros, César Antonio
dc.contributor.authorSchott Verdugo, Eduardo
dc.contributor.authorZarate, Ximena
dc.contributor.authorGarcía Paredes, Luis Enrique
dc.contributor.authorGonzalez-Henriquez, Carmen M.
dc.contributor.authorJessop, Ignacio A.
dc.contributor.authorTundidor Camba, Alain
dc.contributor.authorSobarzo Aucal, Patricio Antonio
dc.contributor.authorTerraza Inostroza, Claudio
dc.date.accessioned2025-05-06T20:57:56Z
dc.date.available2025-05-06T20:57:56Z
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., Schiff 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.format.extent13 páginas
dc.fuente.origenSRIA
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/11534/104037
dc.identifier.wosidWOS:001144217500001
dc.information.autorucEscuela de Química; González Guzmán, Alexis Fabián; S/I; 231896
dc.information.autorucEscuela de Química; Mariman Marchant, Andrea Paz; S/I; 1027496
dc.information.autorucEscuela de Química; Hauyón Sepúlveda, René Alejandro; S/I; 205191
dc.information.autorucEscuela de Química; Pavéz Lizana, Danitza Belén; S/I; 1088612
dc.information.autorucEscuela de Química; Saldías Barros, César Antonio; S/I; 125097
dc.information.autorucEscuela de Química; Schott Verdugo, Eduardo; 0000-0002-2546-304X; 1020229
dc.information.autorucEscuela de Química; García Paredes, Luis Enrique; S/I; 1289482
dc.information.autorucEscuela de Química; Tundidor Camba, Alain; 0000-0001-8653-8722; 189143
dc.information.autorucEscuela de Química; Sobarzo Aucal, Patricio Antonio; 0000-0003-3684-7636; 250231
dc.information.autorucEscuela de Química; Terraza Inostroza, Claudio; 0000-0002-6326-8771; 1001668
dc.issue.numero7
dc.language.isoen
dc.nota.accesocontenido parcial
dc.pagina.final651
dc.pagina.inicio639
dc.publisherRoyal Sociaty of Chemistry
dc.revistaPolymer Chemistry
dc.rightsacceso restringido
dc.subject.ddc510
dc.subject.deweyMatemática física y químicaes_ES
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.codpersvinculados231896
sipa.codpersvinculados1027496
sipa.codpersvinculados205191
sipa.codpersvinculados1088612
sipa.codpersvinculados125097
sipa.codpersvinculados1020229
sipa.codpersvinculados1289482
sipa.codpersvinculados189143
sipa.codpersvinculados250231
sipa.codpersvinculados1001668
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