F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and Benzimidazoles

Graphitic carbon nitride (g-C<sub>3</sub>N<sub>4</sub>) is a metal-free heterogeneous catalyst that has attracted attention because of its good chemical stability, cost-effectiveness, and environmental friendliness. In the work presented herein, F,O,S-codoped carbon nitride w...

Full description

Bibliographic Details
Main Authors: Alberto Santiago-Aliste, Eva Sánchez-Hernández, Celia Andrés-Juan, Pedro Chamorro-Posada, Guillermo Antorrena, Jesús Martín-Gil, Pablo Martín-Ramos
Format: Article
Language:English
Published: MDPI AG 2023-02-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/13/2/385
_version_ 1797621804084232192
author Alberto Santiago-Aliste
Eva Sánchez-Hernández
Celia Andrés-Juan
Pedro Chamorro-Posada
Guillermo Antorrena
Jesús Martín-Gil
Pablo Martín-Ramos
author_facet Alberto Santiago-Aliste
Eva Sánchez-Hernández
Celia Andrés-Juan
Pedro Chamorro-Posada
Guillermo Antorrena
Jesús Martín-Gil
Pablo Martín-Ramos
author_sort Alberto Santiago-Aliste
collection DOAJ
description Graphitic carbon nitride (g-C<sub>3</sub>N<sub>4</sub>) is a metal-free heterogeneous catalyst that has attracted attention because of its good chemical stability, cost-effectiveness, and environmental friendliness. In the work presented herein, F,O,S-codoped carbon nitride was synthesized by heating a mixture of melamine cyanurate and trifluoromethanesulfonic acid at 550 °C for 50 min. The obtained product was characterized by transmission electron microscopy, infrared spectroscopy, X-ray powder diffraction, CHNS elemental analysis, total combustion-ion chromatography, X-ray photoelectron spectroscopy, scanning electron microscopy coupled with energy-dispersive X-ray spectroscopy, and UV-Vis spectroscopy. Results point to an F,O,S-codoped g-C<sub>3</sub>N<sub>4</sub>. The material was applied as a photocatalyst for the formation of benzoxazoles and benzimidazoles by condensation–aromatization of 2-aminophenol or 1,2-phenylenediamine with suitable aldehydes (viz. benzaldehyde, 4-chlorobenzaldehyde, 2-naphthaldehyde, 2-hydroxybenzaldehyde, and 2-methoxybenzaldehyde), obtaining yields of up to 90% in 15 min under visible light irradiation, with good selectivity and reusability. Thus, the reported findings suggest that this F,O,S-codoped g-C<sub>3</sub>N<sub>4</sub> may hold promise as a metal-free photocatalyst for the rapid synthesis of 2-arylbenzoxazoles and 2-arylbenzimidazoles.
first_indexed 2024-03-11T09:01:09Z
format Article
id doaj.art-ad5fb428e6784ceb9815c32c55fe8d7a
institution Directory Open Access Journal
issn 2073-4344
language English
last_indexed 2024-03-11T09:01:09Z
publishDate 2023-02-01
publisher MDPI AG
record_format Article
series Catalysts
spelling doaj.art-ad5fb428e6784ceb9815c32c55fe8d7a2023-11-16T19:42:23ZengMDPI AGCatalysts2073-43442023-02-0113238510.3390/catal13020385F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and BenzimidazolesAlberto Santiago-Aliste0Eva Sánchez-Hernández1Celia Andrés-Juan2Pedro Chamorro-Posada3Guillermo Antorrena4Jesús Martín-Gil5Pablo Martín-Ramos6Department of Agricultural and Forestry Engineering, ETSIIAA, Universidad de Valladolid, Avenida de Madrid 44, 34004 Palencia, SpainDepartment of Agricultural and Forestry Engineering, ETSIIAA, Universidad de Valladolid, Avenida de Madrid 44, 34004 Palencia, SpainGIR Asymmetric Synthesis, Universidad de Valladolid, Campus Miguel Delibes, Paseo Belén 7, 47011 Valladolid, SpainDepartment of Theory of Signal and Communications and Telematic Engineering, ETSIT, Universidad de Valladolid, Paseo de Belén 15, 47011 Valladolid, SpainLaboratorio de Microscopias Avanzadas (LMA), Edificio I+D, Campus Río Ebro, Universidad de Zaragoza, C/Mariano Esquillor s/n, 50018 Zaragoza, SpainDepartment of Agricultural and Forestry Engineering, ETSIIAA, Universidad de Valladolid, Avenida de Madrid 44, 34004 Palencia, SpainDepartment of Agricultural and Forestry Engineering, ETSIIAA, Universidad de Valladolid, Avenida de Madrid 44, 34004 Palencia, SpainGraphitic carbon nitride (g-C<sub>3</sub>N<sub>4</sub>) is a metal-free heterogeneous catalyst that has attracted attention because of its good chemical stability, cost-effectiveness, and environmental friendliness. In the work presented herein, F,O,S-codoped carbon nitride was synthesized by heating a mixture of melamine cyanurate and trifluoromethanesulfonic acid at 550 °C for 50 min. The obtained product was characterized by transmission electron microscopy, infrared spectroscopy, X-ray powder diffraction, CHNS elemental analysis, total combustion-ion chromatography, X-ray photoelectron spectroscopy, scanning electron microscopy coupled with energy-dispersive X-ray spectroscopy, and UV-Vis spectroscopy. Results point to an F,O,S-codoped g-C<sub>3</sub>N<sub>4</sub>. The material was applied as a photocatalyst for the formation of benzoxazoles and benzimidazoles by condensation–aromatization of 2-aminophenol or 1,2-phenylenediamine with suitable aldehydes (viz. benzaldehyde, 4-chlorobenzaldehyde, 2-naphthaldehyde, 2-hydroxybenzaldehyde, and 2-methoxybenzaldehyde), obtaining yields of up to 90% in 15 min under visible light irradiation, with good selectivity and reusability. Thus, the reported findings suggest that this F,O,S-codoped g-C<sub>3</sub>N<sub>4</sub> may hold promise as a metal-free photocatalyst for the rapid synthesis of 2-arylbenzoxazoles and 2-arylbenzimidazoles.https://www.mdpi.com/2073-4344/13/2/385photocatalytic synthesisdoped g-C<sub>3</sub>N<sub>4</sub>2-arylbenzoxazoles2-arylbenzimidazoles
spellingShingle Alberto Santiago-Aliste
Eva Sánchez-Hernández
Celia Andrés-Juan
Pedro Chamorro-Posada
Guillermo Antorrena
Jesús Martín-Gil
Pablo Martín-Ramos
F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and Benzimidazoles
Catalysts
photocatalytic synthesis
doped g-C<sub>3</sub>N<sub>4</sub>
2-arylbenzoxazoles
2-arylbenzimidazoles
title F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and Benzimidazoles
title_full F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and Benzimidazoles
title_fullStr F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and Benzimidazoles
title_full_unstemmed F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and Benzimidazoles
title_short F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and Benzimidazoles
title_sort f o s codoped graphitic carbon nitride as an efficient photocatalyst for the synthesis of benzoxazoles and benzimidazoles
topic photocatalytic synthesis
doped g-C<sub>3</sub>N<sub>4</sub>
2-arylbenzoxazoles
2-arylbenzimidazoles
url https://www.mdpi.com/2073-4344/13/2/385
work_keys_str_mv AT albertosantiagoaliste foscodopedgraphiticcarbonnitrideasanefficientphotocatalystforthesynthesisofbenzoxazolesandbenzimidazoles
AT evasanchezhernandez foscodopedgraphiticcarbonnitrideasanefficientphotocatalystforthesynthesisofbenzoxazolesandbenzimidazoles
AT celiaandresjuan foscodopedgraphiticcarbonnitrideasanefficientphotocatalystforthesynthesisofbenzoxazolesandbenzimidazoles
AT pedrochamorroposada foscodopedgraphiticcarbonnitrideasanefficientphotocatalystforthesynthesisofbenzoxazolesandbenzimidazoles
AT guillermoantorrena foscodopedgraphiticcarbonnitrideasanefficientphotocatalystforthesynthesisofbenzoxazolesandbenzimidazoles
AT jesusmartingil foscodopedgraphiticcarbonnitrideasanefficientphotocatalystforthesynthesisofbenzoxazolesandbenzimidazoles
AT pablomartinramos foscodopedgraphiticcarbonnitrideasanefficientphotocatalystforthesynthesisofbenzoxazolesandbenzimidazoles