Highly crystalline and fluorescent BODIPY-labelled phenyl-triazole-coumarins as n-type semiconducting materials for OFET devices

José Emilio de la Cerda-Pedro; Oscar Javier Hernández-Ortiz; Rosa Angeles Vázquez-García; Efrén V García-Báez; Ramón Gómez-Aguilar; Arián Espinosa-Roa; Norberto Farfán; Itzia I Padilla-Martínez

doi:10.1016/j.heliyon.2023.e23517

Highly crystalline and fluorescent BODIPY-labelled phenyl-triazole-coumarins as n-type semiconducting materials for OFET devices

Heliyon. 2023 Dec 10;10(1):e23517. doi: 10.1016/j.heliyon.2023.e23517. eCollection 2024 Jan 15.

Authors

José Emilio de la Cerda-Pedro¹, Oscar Javier Hernández-Ortiz^{1

2}, Rosa Angeles Vázquez-García², Efrén V García-Báez¹, Ramón Gómez-Aguilar³, Arián Espinosa-Roa⁴, Norberto Farfán⁵, Itzia I Padilla-Martínez¹

Affiliations

¹ Laboratorio de Química Supramolecular y Nanociencias de la Unidad Profesional Interdisciplinaria de Biotecnología del Instituto Politécnico Nacional, Av. Acueducto s/n Barrio la laguna Ticomán, 07340, Ciudad de Mexico, Mexico.
² Área Académica de Ciencias de la Tierra y Materiales, Universidad Autónoma del Estado de Hidalgo, km. 4.5 Carretera Pachuca-Tulancingo, Col. Carboneras 42184, Mineral de la Reforma, Hidalgo Mexico.
³ Unidad Profesional en Ingeniería y Tecnologías Avanzadas del Instituto Politécnico Nacional, Av. I.P.N No. 2580 Col. La Laguna Ticomán, Gustavo A. Madero 07340, Ciudad de Mexico, Mexico.
⁴ CONAHCYT-Centro de Investigación en Química Aplicada Unidad Monterrey, Sur 204 Parque de Innovación e Investigación Tecnológica, Km. 10 autopista al Aeropuerto Internacional Mariano Escobedo, 66628, Apodaca, Nuevo Leon, Mexico.
⁵ Departamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, Circuito Escolar, Ciudad Universitaria 04510, Ciudad de Mexico, Mexico.

Abstract

In this work, the synthesis of BODIPY-phenyl-triazole labelled coumarins (BPhTCs) using a two-step approach is described. The influence of the BODIPY appending on the photophysical, electrochemical and thermal properties of the phenyl-triazole-coumarin precursors (PhTCs) was investigated. Band gap energies were measured by absorption spectroscopy (2.20 ± 0.02 eV in the solid and 2.35 ± 0.01 eV in solution) and cyclic voltammetry (2.10 ± 0.05 eV). The results are supported by DFT calculations confirming the presence of lowest LUMO levels that facilitate the electron injection and stabilize the electron transport. Their charge-transport parameters were measured in Organic Field-Effect Transistor (OFET) devices. BPhTCs showed an ambipolar transistor behavior with good n-type charge mobilities (10^-2 cm²V^-1s^-1) allowing these derivatives to be employed as promising semiconducting crystalline and fluorescent materials with good thermal and air stability up to 250 °C.

Keywords: BODIPY; OFET; Organic field‐effect transistors; Organic semiconductor; Organic small molecule devices; Phenyl-triazole.