Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation
In this study we report on the efficiency of a furane-indole-chromenone-based organic derivative (<b>FIC</b>) as a photocatalyst in the α-arylation of enol acetate upon LED irradiation at 405 nm, and as a photoinitiator/photocatalyst in the free radical polymerization of an acrylate grou...
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2025-01-01
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| author | Aurélien Galibert-Guijarro Adel Noon Joumana Toufaily Tayssir Hamieh Eric Besson Stéphane Gastaldi Jacques Lalevée Laurence Feray |
| author_facet | Aurélien Galibert-Guijarro Adel Noon Joumana Toufaily Tayssir Hamieh Eric Besson Stéphane Gastaldi Jacques Lalevée Laurence Feray |
| author_sort | Aurélien Galibert-Guijarro |
| collection | DOAJ |
| description | In this study we report on the efficiency of a furane-indole-chromenone-based organic derivative (<b>FIC</b>) as a photocatalyst in the α-arylation of enol acetate upon LED irradiation at 405 nm, and as a photoinitiator/photocatalyst in the free radical polymerization of an acrylate group in the presence of <i>bis</i>-(4-<i>tert</i>-butylphenyl)iodonium hexafluorophosphate (Iod) as an additive, or in the presence of both Iod and ethyl-4-(dimethyl amino) benzoate (EDB) under LED irradiation at 365 nm. The photochemical properties of this new light-sensitive compound are described, and the wide redox window (3.27 eV) and the high excited-state potentials <b>FIC*</b>/<b>FIC<sup>●−</sup></b> (+2.64 V vs. SCE) and <b>FIC<sup>●+</sup></b>/<b>FIC*</b> (−2.41 V vs. SCE) offered by this photocatalyst are revealed. The chemical mechanisms that govern the radical chemistry are discussed by means of different techniques, including fluorescence-quenching experiments, UV-visible absorption and fluorescence spectroscopy, and cyclic voltammetry analysis. |
| format | Article |
| id | doaj-art-4b7d570f446a4c12b461437671dea41c |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-4b7d570f446a4c12b461437671dea41c2025-01-24T13:43:19ZengMDPI AGMolecules1420-30492025-01-0130226510.3390/molecules30020265Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED IrradiationAurélien Galibert-Guijarro0Adel Noon1Joumana Toufaily2Tayssir Hamieh3Eric Besson4Stéphane Gastaldi5Jacques Lalevée6Laurence Feray7Aix Marseille Univ, CNRS, ICR, 13013 Marseille, FranceUniversité de Haute-Alsace, CNRS, IS2M UMR 7361, F-68100 Mulhouse, FranceLaboratory of Materials, Catalysis, Environment and Analytical Methods (MCEMA), Faculty of Sciences, Doctoral School of Sciences and Technology (EDST), Lebanese University, Beirut 6573-14, LebanonUniversité de Haute-Alsace, CNRS, IS2M UMR 7361, F-68100 Mulhouse, FranceAix Marseille Univ, CNRS, ICR, 13013 Marseille, FranceAix Marseille Univ, CNRS, ICR, 13013 Marseille, FranceUniversité de Haute-Alsace, CNRS, IS2M UMR 7361, F-68100 Mulhouse, FranceAix Marseille Univ, CNRS, ICR, 13013 Marseille, FranceIn this study we report on the efficiency of a furane-indole-chromenone-based organic derivative (<b>FIC</b>) as a photocatalyst in the α-arylation of enol acetate upon LED irradiation at 405 nm, and as a photoinitiator/photocatalyst in the free radical polymerization of an acrylate group in the presence of <i>bis</i>-(4-<i>tert</i>-butylphenyl)iodonium hexafluorophosphate (Iod) as an additive, or in the presence of both Iod and ethyl-4-(dimethyl amino) benzoate (EDB) under LED irradiation at 365 nm. The photochemical properties of this new light-sensitive compound are described, and the wide redox window (3.27 eV) and the high excited-state potentials <b>FIC*</b>/<b>FIC<sup>●−</sup></b> (+2.64 V vs. SCE) and <b>FIC<sup>●+</sup></b>/<b>FIC*</b> (−2.41 V vs. SCE) offered by this photocatalyst are revealed. The chemical mechanisms that govern the radical chemistry are discussed by means of different techniques, including fluorescence-quenching experiments, UV-visible absorption and fluorescence spectroscopy, and cyclic voltammetry analysis.https://www.mdpi.com/1420-3049/30/2/265organic photocatalystfree radical polymerizationalkene arylationphotoredox catalysisredox potentialphotoinduced electron transfer |
| spellingShingle | Aurélien Galibert-Guijarro Adel Noon Joumana Toufaily Tayssir Hamieh Eric Besson Stéphane Gastaldi Jacques Lalevée Laurence Feray Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation Molecules organic photocatalyst free radical polymerization alkene arylation photoredox catalysis redox potential photoinduced electron transfer |
| title | Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation |
| title_full | Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation |
| title_fullStr | Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation |
| title_full_unstemmed | Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation |
| title_short | Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation |
| title_sort | furan indole chromenone based organic photocatalyst for α arylation of enol acetate and free radical polymerization under led irradiation |
| topic | organic photocatalyst free radical polymerization alkene arylation photoredox catalysis redox potential photoinduced electron transfer |
| url | https://www.mdpi.com/1420-3049/30/2/265 |
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