109589 20230519145404.0 doi 10.1021/acs.joc.0c02438 sideral 123284 ART-2021-123284 eng Tejeda-Orusco, V. Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties 2021 Access copy available to the general public Unrestricted 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). 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 info:eu-repo/semantics/openAccess by http://creativecommons.org/licenses/by/3.0/es/ 4.198 2021 CHEMISTRY, ORGANIC 12 / 57 = 0.211 2021 Q1 T1 0.983 2021 Organic Chemistry 2021 Q1 info:eu-repo/semantics/article info:eu-repo/semantics/submittedVersion Andreu, R. Universidad de Zaragoza (orcid)0000-0002-3206-9868 Orduna, J. (orcid)0000-0003-3514-2570 Villacampa, B. Universidad de Zaragoza (orcid)0000-0001-9814-0834 Franco, S. Universidad de Zaragoza (orcid)0000-0001-9747-1789 Civera, A. Universidad de Zaragoza (orcid)0000-0001-7719-6388 2013 765 Universidad de Zaragoza Dpto. Química Orgánica Área Química Orgánica 2003 395 Universidad de Zaragoza Dpto. Física Materia Condensa. Área Física Materia Condensada 2008 780 Universidad de Zaragoza Dpto. Produc.Animal Cienc.Ali. Área Tecnología de Alimentos 86 (2021), 3152-3163 J. org. chem. Journal of Organic Chemistry 0022-3263 1378155 http://zaguan.unizar.es/record/109589/files/texto_completo.pdf Preprint 1118454 http://zaguan.unizar.es/record/109589/files/texto_completo.jpg?subformat=icon icon Preprint oai:zaguan.unizar.es:109589 articulos driver 2023-05-18-13:44:27 ARTICLE