Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation

Aurélien Galibert-Guijarro; Adel Noon; Joumana Toufaily; Tayssir Hamieh; Eric Besson; Stéphane Gastaldi; Jacques Lalevée; Laurence Feray

doi:10.3390/molecules30020265

Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation

Aurélien Galibert-Guijarro
, Adel Noon
, Joumana Toufaily
, Tayssir Hamieh
, Eric Besson
, Stéphane Gastaldi
, Jacques Lalevée^*
, Laurence Feray^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

In this study we report on the efficiency of a furane-indole-chromenone-based organic derivative ( ) as a photocatalyst in the a-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 -(4- -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 / (+2.64 V vs. SCE) and / (-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.

Original language	English
Article number	265
Journal	Molecules
Volume	30
Issue number	2
DOIs	https://doi.org/10.3390/molecules30020265
Publication status	Published - 11 Jan 2025

Keywords

alkene arylation
free radical polymerization
organic photocatalyst
photoinduced electron transfer
photoredox catalysis
redox potential

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title = "Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation",

abstract = "In this study we report on the efficiency of a furane-indole-chromenone-based organic derivative ( ) as a photocatalyst in the a-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 -(4- -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 / (+2.64 V vs. SCE) and / (-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.",

keywords = "alkene arylation, free radical polymerization, organic photocatalyst, photoinduced electron transfer, photoredox catalysis, redox potential",

author = "Aur{\'e}lien Galibert-Guijarro and Adel Noon and Joumana Toufaily and Tayssir Hamieh and Eric Besson and St{\'e}phane Gastaldi and Jacques Lalev{\'e}e and Laurence Feray",

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doi = "10.3390/molecules30020265",

language = "English",

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TY - JOUR

T1 - Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation

AU - Galibert-Guijarro, Aurélien

AU - Noon, Adel

AU - Toufaily, Joumana

AU - Hamieh, Tayssir

AU - Besson, Eric

AU - Gastaldi, Stéphane

AU - Lalevée, Jacques

AU - Feray, Laurence

PY - 2025/1/11

Y1 - 2025/1/11

N2 - In this study we report on the efficiency of a furane-indole-chromenone-based organic derivative ( ) as a photocatalyst in the a-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 -(4- -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 / (+2.64 V vs. SCE) and / (-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.

AB - In this study we report on the efficiency of a furane-indole-chromenone-based organic derivative ( ) as a photocatalyst in the a-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 -(4- -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 / (+2.64 V vs. SCE) and / (-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.

KW - alkene arylation

KW - free radical polymerization

KW - organic photocatalyst

KW - photoinduced electron transfer

KW - photoredox catalysis

KW - redox potential

U2 - 10.3390/molecules30020265

DO - 10.3390/molecules30020265

M3 - Article

SN - 1420-3049

VL - 30

JO - Molecules

JF - Molecules

IS - 2

M1 - 265

ER -

Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation

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Keywords

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