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Synthesis, optical, electrochemical, and magnetic properties of new ferrocenyl chalcone semiconductors for optoelectronic applications

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Abstract

A ferrocenyl chalcone (OFcPV) with attractive optical and magnetic properties for its potential application in optoelectronic devices, excellent processability in solution, and thermal stability is reported. It was derived from the synthesis of ferrocenyl chalcone with different degrees of conjugation and the preliminary selection of the most attractive molecule based on its linear optical and electrochemical properties, and processability. Three ferrocene-derived compounds: a low-molecular weight molecule (3FcPV), an oligomer (OFcPV), and a polymer (PFcPV) were synthesized through Friedel–Crafts reactions and aldol condensations. The chemical structure of the compounds has been elucidated by proton nuclear magnetic resonance and Fourier-transform infrared spectroscopies. UV–Vis and fluorescence spectroscopies were used to evaluate the optical properties of these new compounds. The frontier orbitals levels of the materials deposited as films were determined using cyclic voltammetry. The optical bandgaps for 3FcPV, OFcPV, and PFcPV were 2.8, 2.4, and 2.36 eV, respectively. These results place these materials within the organic semiconductors and evidence the influence of the degree of electronic conjugation of the molecule in the reduction of the bandgap. The results showed that the oligomer and the polymer possess similar electronic and optical properties. However, the oligomer solubility improves the processability necessary for the manufacturing photonic devices. OFcPV was characterized by Z-scan technique, and the results indicate that OFcPV is candidate to be used as an optical limiter, fast optical switch, or optical logic gates. Also, OFcPV exhibits quasi-superparamagnetic behavior resulting from the iron disposal in the structure.

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Acknowledgements

The authors acknowledge support of project CONACyT-FSSEP02-C-2018-2. First author acknowledges the support for a scholarship given by CONACYT: 330199 and SEP-PROJECT 221360. We would also like to thank Fidel Pérez and Felix Sánchez for technical assistance.

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Authors and Affiliations

  1. Área Académica de Ciencias de la Tierra y Materiales, Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Carretera Pachuca-Tulancingo Km. 4.5, Ciudad del Conocimiento, Mineral de la Reforma, Hidalgo, Mexico

    Oscar Javier Hernández-Ortiz, Jesús Emmanuel Cerón-Castelán, Verónica Salazar-Pereda, María Aurora Veloz-Rodríguez, Azdrúbal Lobo-Guerrero & Rosa Angeles Vázquez-García

  2. CONACYT-Centro de Investigación en Química Aplicada, Parque de Innovación e Investigación Tecnológica (PIIT), Apodaca, NL, Mexico

    Arian Espinosa-Roa

  3. Centro de Investigaciones en Óptica A.C, Loma del Bosque # 115, Col. Lomas del Campestre, 37150, León, Guanajuato, Mexico

    Mario Alejandro Rodríguez-Rivera

  4. División de Posgrado, Universidad Politécnica de Tulancingo, Calle Ingenierías # 100, Huapalcalco, 43629, Tulancingo de Bravo, Hidalgo, Mexico

    Francisco Misael Muñoz-Pérez & José Gabriel Ortega-Mendoza

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  1. Oscar Javier Hernández-Ortiz
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  10. Rosa Angeles Vázquez-García
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Contributions

Synthesis and chemical characterization of 3FcPV, OFcPV, and PFcPv were conducted by Oscar Javier Hernández Ortiz, Jesús Emmanuel Ceron Castelan, Rosa Angeles Vázquez Garcia, Mario Alejandro Rodríguez Rivera, and Verónica Salazar Pereda. Electrochemical characterization by María Aurora Veloz Rodríguez and Oscar Javier Hernández Ortiz. The theoretical study (DFT) by Oscar Javier Hernandez Ortiz and Arian Espinosa Roa. Magnetic characterization by Azdrubal Lobo Guerrero. Non-linear charaterization by Francisco Misael Muñoz Pérez and José Gabriel Ortega Mendoza. All authors contributed equally to the analysis and interpretation of the results. All the authors are in agreement with the last version.

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Correspondence to Rosa Angeles Vázquez-García.

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Hernández-Ortiz, O.J., Cerón-Castelán, J.E., Muñoz-Pérez, F.M. et al. Synthesis, optical, electrochemical, and magnetic properties of new ferrocenyl chalcone semiconductors for optoelectronic applications. J Mater Sci: Mater Electron 31, 3342–3353 (2020). https://doi.org/10.1007/s10854-020-02882-1

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