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Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Intramolecular charge transfer (ICT) effects are responsible for the photoluminescent properties of coumarins. Hence, optical properties with different applications can be obtained by ICT modulation. Herein, four 3-acetyl-2H-chromen-2-ones (1a–d) and their corresponding fluorescent hybrids 3- (pheny...

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Autores principales: Villa-Martínez, Cesar A., Magaña-Vergara, Nancy E., Rodríguez, Mario, Mojica-Sánchez, Juan P., Ramos-Organillo, Ángel A., Barroso-Flores, Joaquín, Padilla-Martínez, Itzia I., Martínez-Martínez, Francisco J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9227197/
https://www.ncbi.nlm.nih.gov/pubmed/35744802
http://dx.doi.org/10.3390/molecules27123677
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author Villa-Martínez, Cesar A.
Magaña-Vergara, Nancy E.
Rodríguez, Mario
Mojica-Sánchez, Juan P.
Ramos-Organillo, Ángel A.
Barroso-Flores, Joaquín
Padilla-Martínez, Itzia I.
Martínez-Martínez, Francisco J.
author_facet Villa-Martínez, Cesar A.
Magaña-Vergara, Nancy E.
Rodríguez, Mario
Mojica-Sánchez, Juan P.
Ramos-Organillo, Ángel A.
Barroso-Flores, Joaquín
Padilla-Martínez, Itzia I.
Martínez-Martínez, Francisco J.
author_sort Villa-Martínez, Cesar A.
collection PubMed
description Intramolecular charge transfer (ICT) effects are responsible for the photoluminescent properties of coumarins. Hence, optical properties with different applications can be obtained by ICT modulation. Herein, four 3-acetyl-2H-chromen-2-ones (1a–d) and their corresponding fluorescent hybrids 3- (phenylhydrazone)-chromen-2-ones (2a–d) were synthesized in 74–65% yields. The UV-Vis data were in the 295–428 nm range. The emission depends on the substituent in position C-7 bearing electron-donating groups. Compounds 1b–d showed good optical properties due to the D-π-A structural arrangement. In compounds 2a–d, there is a quenching effect of fluorescence in solution. However, in the solid, an increase is shown due to an aggregation-induced emission (AIE) effect given by the rotational restraints and stacking in the crystal. Computational calculations of the HOMO-LUMO orbitals indicate high absorbance and emission values of the molecules, and gap values represent the bathochromic effect and the electronic efficiency of the compounds. Compounds 1a–d and 2a–d are good candidates for optical applications, such as OLEDs, organic solar cells, or fluorescence markers.
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spelling pubmed-92271972022-06-25 Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives Villa-Martínez, Cesar A. Magaña-Vergara, Nancy E. Rodríguez, Mario Mojica-Sánchez, Juan P. Ramos-Organillo, Ángel A. Barroso-Flores, Joaquín Padilla-Martínez, Itzia I. Martínez-Martínez, Francisco J. Molecules Article Intramolecular charge transfer (ICT) effects are responsible for the photoluminescent properties of coumarins. Hence, optical properties with different applications can be obtained by ICT modulation. Herein, four 3-acetyl-2H-chromen-2-ones (1a–d) and their corresponding fluorescent hybrids 3- (phenylhydrazone)-chromen-2-ones (2a–d) were synthesized in 74–65% yields. The UV-Vis data were in the 295–428 nm range. The emission depends on the substituent in position C-7 bearing electron-donating groups. Compounds 1b–d showed good optical properties due to the D-π-A structural arrangement. In compounds 2a–d, there is a quenching effect of fluorescence in solution. However, in the solid, an increase is shown due to an aggregation-induced emission (AIE) effect given by the rotational restraints and stacking in the crystal. Computational calculations of the HOMO-LUMO orbitals indicate high absorbance and emission values of the molecules, and gap values represent the bathochromic effect and the electronic efficiency of the compounds. Compounds 1a–d and 2a–d are good candidates for optical applications, such as OLEDs, organic solar cells, or fluorescence markers. MDPI 2022-06-08 /pmc/articles/PMC9227197/ /pubmed/35744802 http://dx.doi.org/10.3390/molecules27123677 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Villa-Martínez, Cesar A.
Magaña-Vergara, Nancy E.
Rodríguez, Mario
Mojica-Sánchez, Juan P.
Ramos-Organillo, Ángel A.
Barroso-Flores, Joaquín
Padilla-Martínez, Itzia I.
Martínez-Martínez, Francisco J.
Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives
title Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives
title_full Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives
title_fullStr Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives
title_full_unstemmed Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives
title_short Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives
title_sort synthesis, optical characterization in solution and solid-state, and dft calculations of 3-acetyl and 3-(1′-(2′-phenylhydrazono)ethyl)-coumarin-(7)-substituted derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9227197/
https://www.ncbi.nlm.nih.gov/pubmed/35744802
http://dx.doi.org/10.3390/molecules27123677
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