000109589 001__ 109589
000109589 005__ 20230519145404.0
000109589 0247_ $$2doi$$a10.1021/acs.joc.0c02438
000109589 0248_ $$2sideral$$a123284
000109589 037__ $$aART-2021-123284
000109589 041__ $$aeng
000109589 100__ $$aTejeda-Orusco, V.
000109589 245__ $$aTwisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4 H-Pyranylidene Donor: Synthesis and Optical Properties
000109589 260__ $$c2021
000109589 5060_ $$aAccess copy available to the general public$$fUnrestricted
000109589 5203_ $$aThree 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).
000109589 536__ $$9info:eu-repo/grantAgreement/ES/DGA-FEDER-FSE 2014–2020/E14-17R$$9info:eu-repo/grantAgreement/ES/MICINN/PID2019-104307GB-I00-AEI-10.13039-501100011033$$9info:eu-repo/grantAgreement/ES/UZ/UZ2019-CIE-01
000109589 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000109589 590__ $$a4.198$$b2021
000109589 592__ $$a0.983$$b2021
000109589 591__ $$aCHEMISTRY, ORGANIC$$b12 / 57 = 0.211$$c2021$$dQ1$$eT1
000109589 593__ $$aOrganic Chemistry$$c2021$$dQ1
000109589 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/submittedVersion
000109589 700__ $$0(orcid)0000-0002-3206-9868$$aAndreu, R.$$uUniversidad de Zaragoza
000109589 700__ $$0(orcid)0000-0003-3514-2570$$aOrduna, J.
000109589 700__ $$0(orcid)0000-0001-9814-0834$$aVillacampa, B.$$uUniversidad de Zaragoza
000109589 700__ $$0(orcid)0000-0001-9747-1789$$aFranco, S.$$uUniversidad de Zaragoza
000109589 700__ $$0(orcid)0000-0001-7719-6388$$aCivera, A.$$uUniversidad de Zaragoza
000109589 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000109589 7102_ $$12003$$2395$$aUniversidad de Zaragoza$$bDpto. Física Materia Condensa.$$cÁrea Física Materia Condensada
000109589 7102_ $$12008$$2780$$aUniversidad de Zaragoza$$bDpto. Produc.Animal Cienc.Ali.$$cÁrea Tecnología de Alimentos
000109589 773__ $$g86 (2021), 3152-3163$$pJ. org. chem.$$tJournal of Organic Chemistry$$x0022-3263
000109589 8564_ $$s1378155$$uhttps://zaguan.unizar.es/record/109589/files/texto_completo.pdf$$yPreprint
000109589 8564_ $$s1118454$$uhttps://zaguan.unizar.es/record/109589/files/texto_completo.jpg?subformat=icon$$xicon$$yPreprint
000109589 909CO $$ooai:zaguan.unizar.es:109589$$particulos$$pdriver
000109589 951__ $$a2023-05-18-13:44:27
000109589 980__ $$aARTICLE