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Chemical engineering around the 5,12-dihydroindolo[3,2-a]carbazole scaffold: Fine tuning of the optical properties of visible light photoinitiators of polymerization
European Polymer Journal ( IF 5.8 ) Pub Date : 2022-04-23 , DOI: 10.1016/j.eurpolymj.2022.111218
Fatima Hammoud 1, 2, 3 , Akram Hijazi 3 , Malika Ibrahim-Ouali 4 , Jacques Lalevée 1, 2 , Frédéric Dumur 5
Affiliation  

5,12-Dihydroindolo[3,2-a]carbazole is a promising scaffold for the design of visible light photoinitiators of polymerization due to the simultaneous presence of two carbazole moieties that can be differently functionalized. Notably, redshift of the absorption spectra can be facilely obtained by nitration of one of the two carbazoles, the second carbazole group being functionalized with various groups. Dinitration of 5,12-dihydroindolo[3,2-a]carbazole is another efficient approach for designing dyes with strong absorptions extending over the visible range. In this work, a series of 36 compounds never reported in the literature and differing by the substitution pattern have been designed and synthesized. Notably, the possibility to design push–pull dyes by Knoevenagel and Claisen Schmidt reactions, to introduce electroactive groups such as thiophene by Suzuki cross-coupling reactions or to design water soluble chromophore has been explored. To evidence the interest of these structures, photopolymerization experiments have been carried out at 405 nm and the polymerization of acrylates has been examined in thick and thin films. To support the polymerization efficiency, mechanisms involved in the free radical polymerization of acrylates have been established by the combination of various techniques including UV–visible absorption and fluorescence spectroscopy, cyclic voltammetry and photolysis experiments.



中文翻译:

5,12-二氢吲哚[3,2-a]咔唑支架周围的化学工程:微调可见光聚合光引发剂的光学性质

由于同时存在两个可以不同官能化的咔唑部分,5,12-二氢吲哚[3,2- a ]咔唑是用于设计聚合的可见光光引发剂的有前途的支架。值得注意的是,吸收光谱的红移可以通过两种咔唑之一的硝化容易地获得,第二咔唑基团被各种基团官能化。5,12-二氢吲哚[3,2- a的二硝化]咔唑是另一种设计在可见光范围内具有强吸收的染料的有效方法。在这项工作中,设计和合成了一系列 36 种从未在文献中报道过且因取代模式不同而不同的化合物。值得注意的是,已经探索了通过 Knoevenagel 和 Claisen Schmidt 反应设计推拉染料、通过 Suzuki 交叉偶联反应引入噻吩等电活性基团或设计水溶性生色团的可能性。为了证明对这些结构的兴趣,已经在 405 nm 进行了光聚合实验,并在厚膜和薄膜中检查了丙烯酸酯的聚合。为了支持聚合效率,

更新日期:2022-04-23
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