5,12-Dihydroindolo[3,2-a]carbazole: A ...
Document type :
Article dans une revue scientifique
Permalink :
Title :
5,12-Dihydroindolo[3,2-a]carbazole: A promising scaffold for the design of visible light photoinitiators of polymerization
Author(s) :
Hammoud, Fatima [Auteur]
Hijazi, Akram [Auteur]
Duval, Sylvain [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Lalevée, Jacques [Auteur]
Dumur, Frédéric [Auteur]
Hijazi, Akram [Auteur]
Duval, Sylvain [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Lalevée, Jacques [Auteur]
Dumur, Frédéric [Auteur]
Journal title :
European Polymer Journal
Volume number :
162
Pages :
110880
Publisher :
Elsevier
Publication date :
2022-01-05
ISSN :
0014-3057
English keyword(s) :
Carbazole
photopolymerization
dyes
asymmetric substitution
photopolymerization
dyes
asymmetric substitution
HAL domain(s) :
Chimie/Chimie inorganique
Chimie/Matériaux
Chimie/Matériaux
English abstract : [en]
5,12-Dihydroindolo[3,2-a]carbazole is a polycyclic structure combining in its scaffold two carbazole moieties sharing a fused aromatic ring. Since the pioneering works reported in 2019 on this structure concerning the ...
Show more >5,12-Dihydroindolo[3,2-a]carbazole is a polycyclic structure combining in its scaffold two carbazole moieties sharing a fused aromatic ring. Since the pioneering works reported in 2019 on this structure concerning the substitution of the two carbazoles by similar functional groups, no recent investigation has been devoted to asymmetrize the substitution of the two carbazoles. In this work, a series of 13 compounds based on the 5,12-dihydroindolo[3,2-a]carbazole scaffold is presented. By carefully controlling the reaction conditions, functional groups such as a formyl, a nitro or an acetyl group could be selectively introduced on one of the two carbazoles. By combining X-ray diffraction and 2D NMR experiments, the higher reactivity of one of the two carbazoles could be clearly evidenced, enabling to generate asymmetrically substituted structures. Thanks to this unprecedented approach on the 5,12-dihydroindolo[3,2-a]carbazole scaffold, the absorption of the resulting dyes could be shifted towards the visible range whereas the parent structure (5,12-dihexyl-6,7-diphenyl-5,12-dihydroindolo[3,2-a]carbazole) exhibits a strongly UV-centered absorption. In light of their visible light absorption properties, several dyes have been examined as photoinitiators of polymerization activable at 405 nm and under low light intensity in two-component photoinitiating systems for the free radical polymerization of acrylates or the cationic polymerization of epoxides. Chemical mechanisms supporting the different polymerization processes have been fully elucidated by combining several techniques including cyclic voltammetry, UV–visible absorption and photoluminescence spectroscopy as well as photolysis experiments.Show less >
Show more >5,12-Dihydroindolo[3,2-a]carbazole is a polycyclic structure combining in its scaffold two carbazole moieties sharing a fused aromatic ring. Since the pioneering works reported in 2019 on this structure concerning the substitution of the two carbazoles by similar functional groups, no recent investigation has been devoted to asymmetrize the substitution of the two carbazoles. In this work, a series of 13 compounds based on the 5,12-dihydroindolo[3,2-a]carbazole scaffold is presented. By carefully controlling the reaction conditions, functional groups such as a formyl, a nitro or an acetyl group could be selectively introduced on one of the two carbazoles. By combining X-ray diffraction and 2D NMR experiments, the higher reactivity of one of the two carbazoles could be clearly evidenced, enabling to generate asymmetrically substituted structures. Thanks to this unprecedented approach on the 5,12-dihydroindolo[3,2-a]carbazole scaffold, the absorption of the resulting dyes could be shifted towards the visible range whereas the parent structure (5,12-dihexyl-6,7-diphenyl-5,12-dihydroindolo[3,2-a]carbazole) exhibits a strongly UV-centered absorption. In light of their visible light absorption properties, several dyes have been examined as photoinitiators of polymerization activable at 405 nm and under low light intensity in two-component photoinitiating systems for the free radical polymerization of acrylates or the cationic polymerization of epoxides. Chemical mechanisms supporting the different polymerization processes have been fully elucidated by combining several techniques including cyclic voltammetry, UV–visible absorption and photoluminescence spectroscopy as well as photolysis experiments.Show less >
Language :
Anglais
Peer reviewed article :
Oui
Audience :
Internationale
Popular science :
Non
Other project(s) or funding source(s) :
Aix Marseille University
Centre National de la Recherche Scientifique (CNRS)
Centre National de la Recherche Scientifique (CNRS)
Administrative institution(s) :
Université de Lille
CNRS
Centrale Lille
ENSCL
Univ. Artois
CNRS
Centrale Lille
ENSCL
Univ. Artois
Collections :
Research team(s) :
Matériaux hybrides (MATHYB)
Submission date :
2023-11-17T14:18:52Z
2023-12-08T10:01:55Z
2023-12-08T10:01:55Z
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