Academic Journal
Twisted one-dimensional charge transfer and related Y-shaped chromophores with a 4H-pyranylidene donor: Synthesis and optical properties
| العنوان: | Twisted one-dimensional charge transfer and related Y-shaped chromophores with a 4H-pyranylidene donor: Synthesis and optical properties |
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| المؤلفون: | Tejeda-Orusco, Víctor, Andreu, Raquel, Orduna, Jesús, Villacampa, Belén, Franco, Santiago, Civera, Alba |
| المساهمون: | Ministerio de Ciencia, Innovación y Universidades (España), Agencia Estatal de Investigación (España), European Commission, Gobierno de Aragón, Universidad de Zaragoza |
| بيانات النشر: | American Chemical Society |
| سنة النشر: | 2021 |
| المجموعة: | Digital.CSIC (Consejo Superior de Investigaciones Científicas / Spanish National Research Council) |
| الوصف: | 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 π-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 μβ values (except for thiobarbiturate derivatives). ; Financial support from the Ministerio de Ciencia e Innovación (PID2019-104307GB-I00/AEI/10.13039/501100011033), Gobierno de Aragón-FEDER-Fondo Social Europeo 2014–2020 (E14_17R), and University of Zaragoza (UZ2019-CIE-01) is gratefully acknowledged. ; Peer reviewed |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| تدمد: | 1520-6904 |
| Relation: | #PLACEHOLDER_PARENT_METADATA_VALUE#; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-104307GB-I00/ES/DISEÑO Y EVALUACION DE SISTEMAS PI CONJUGADOS PARA APLICACIONES OPTICAS Y FOTOVOLTAICAS/; Postprint; https://doi.org/10.1021/acs.joc.0c02438; Sí; Journal of Organic Chemistry 86(4): 3152-3163 (2021); http://hdl.handle.net/10261/266322; http://dx.doi.org/10.13039/501100007041; http://dx.doi.org/10.13039/501100011033; http://dx.doi.org/10.13039/501100000780; http://dx.doi.org/10.13039/501100010067 |
| DOI: | 10.1021/acs.joc.0c02438 |
| DOI: | 10.13039/501100007041 |
| DOI: | 10.13039/501100011033 |
| DOI: | 10.13039/501100000780 |
| DOI: | 10.13039/501100010067 |
| الاتاحة: | http://hdl.handle.net/10261/266322 https://doi.org/10.1021/acs.joc.0c02438 https://doi.org/10.13039/501100007041 https://doi.org/10.13039/501100011033 https://doi.org/10.13039/501100000780 https://doi.org/10.13039/501100010067 |
| Rights: | open |
| رقم الانضمام: | edsbas.EAE50A5E |
| قاعدة البيانات: | BASE |
| تدمد: | 15206904 |
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| DOI: | 10.1021/acs.joc.0c02438 |