Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties

Three series of push-pull derivatives bearing 4H-pyranylidene as electron donor group and a variety of acceptors were designed. On one hand, one-dimensional chromophores with a thiophene ring (series 1H) or 5-dimethylaminothiophene moiety (series 1N) as an auxiliary donor, non-coplanar with the p-co...

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Autores: Tejeda-Orusco, V., Andreu, R., Orduna, J., Villacampa, B., Franco, S., Civera, A.
Tipo de recurso: artículo
Estado:Versión enviada para evaluación y publicación
Fecha de publicación:2021
País:España
Institución:Universidad de Zaragoza
Repositorio:Zaguán. Repositorio Digital de la Universidad de Zaragoza
OAI Identifier:oai:zaguan.unizar.es:109589
Acceso en línea:http://zaguan.unizar.es/record/109589
Access Level:acceso abierto
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spelling Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical PropertiesTejeda-Orusco, V.Andreu, R.Orduna, J.Villacampa, B.Franco, S.Civera, A.Three series of push-pull derivatives bearing 4H-pyranylidene as electron donor group and a variety of acceptors were designed. On one hand, one-dimensional chromophores with a thiophene ring (series 1H) or 5-dimethylaminothiophene moiety (series 1N) as an auxiliary donor, non-coplanar with the p-conjugated system, were synthesized. On the other hand, related two-dimensional (2D) Y-shaped chromophores (series 2) were also prepared to compare how the diverse architectures affect the electrochemical, linear, and second-order nonlinear optical (NLO) properties. The presence of the 5-dimethylaminothiophene moiety in the exocyclic C= C bond of the pyranylidene unit gives rise to oxidation potentials rarely low, and the protonation (with an excess of trifluoroacetic acid) of its derivatives results in the apparition of a new blue-shifted band in the UV-visible spectra. The analysis of the properties of derivatives with and without the additional thiophene ring shows that this auxiliary donor leads to a higher NLO response, accompanied by an enhanced transparency. Y-shaped chromophores of series 2 present a blue-shifted absorption, higher molar extinction coefficients, and higher Eox values compared to their linear twisted counterparts. As concerns NLO properties, 2D Y-shaped architecture gives rise to somewhat lower µß values (except for thiobarbiturate derivatives).2021info:eu-repo/semantics/articleinfo:eu-repo/semantics/submittedVersionapplication/pdfhttp://zaguan.unizar.es/record/109589reponame:Zaguán. Repositorio Digital de la Universidad de Zaragozainstname:Universidad de ZaragozaInglésinfo:eu-repo/grantAgreement/ES/DGA-FEDER-FSE 2014–2020/E14-17Rinfo:eu-repo/grantAgreement/ES/MICINN/PID2019-104307GB-I00-AEI-10.13039-501100011033info:eu-repo/grantAgreement/ES/UZ/UZ2019-CIE-01info:eu-repo/semantics/openAccessoai:zaguan.unizar.es:1095892026-05-29T13:59:51Z
dc.title.none.fl_str_mv Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
title Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
spellingShingle Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
Tejeda-Orusco, V.
title_short Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
title_full Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
title_fullStr Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
title_full_unstemmed Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
title_sort Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
dc.creator.none.fl_str_mv Tejeda-Orusco, V.
Andreu, R.
Orduna, J.
Villacampa, B.
Franco, S.
Civera, A.
author Tejeda-Orusco, V.
author_facet Tejeda-Orusco, V.
Andreu, R.
Orduna, J.
Villacampa, B.
Franco, S.
Civera, A.
author_role author
author2 Andreu, R.
Orduna, J.
Villacampa, B.
Franco, S.
Civera, A.
author2_role author
author
author
author
author
description Three series of push-pull derivatives bearing 4H-pyranylidene as electron donor group and a variety of acceptors were designed. On one hand, one-dimensional chromophores with a thiophene ring (series 1H) or 5-dimethylaminothiophene moiety (series 1N) as an auxiliary donor, non-coplanar with the p-conjugated system, were synthesized. On the other hand, related two-dimensional (2D) Y-shaped chromophores (series 2) were also prepared to compare how the diverse architectures affect the electrochemical, linear, and second-order nonlinear optical (NLO) properties. The presence of the 5-dimethylaminothiophene moiety in the exocyclic C= C bond of the pyranylidene unit gives rise to oxidation potentials rarely low, and the protonation (with an excess of trifluoroacetic acid) of its derivatives results in the apparition of a new blue-shifted band in the UV-visible spectra. The analysis of the properties of derivatives with and without the additional thiophene ring shows that this auxiliary donor leads to a higher NLO response, accompanied by an enhanced transparency. Y-shaped chromophores of series 2 present a blue-shifted absorption, higher molar extinction coefficients, and higher Eox values compared to their linear twisted counterparts. As concerns NLO properties, 2D Y-shaped architecture gives rise to somewhat lower µß values (except for thiobarbiturate derivatives).
publishDate 2021
dc.date.none.fl_str_mv 2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/submittedVersion
format article
status_str submittedVersion
dc.identifier.none.fl_str_mv http://zaguan.unizar.es/record/109589
url http://zaguan.unizar.es/record/109589
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/ES/DGA-FEDER-FSE 2014–2020/E14-17R
info:eu-repo/grantAgreement/ES/MICINN/PID2019-104307GB-I00-AEI-10.13039-501100011033
info:eu-repo/grantAgreement/ES/UZ/UZ2019-CIE-01
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
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publisher.none.fl_str_mv
dc.source.none.fl_str_mv reponame:Zaguán. Repositorio Digital de la Universidad de Zaragoza
instname:Universidad de Zaragoza
instname_str Universidad de Zaragoza
reponame_str Zaguán. Repositorio Digital de la Universidad de Zaragoza
collection Zaguán. Repositorio Digital de la Universidad de Zaragoza
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