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Novel D–π-A and A–π-D–π-A three-component photoinitiating systems based on carbazole/triphenylamino based chalcones and application in 3D and 4D printing
Polymer Chemistry ( IF 4.6 ) Pub Date : 2020-09-21 , DOI: 10.1039/d0py01197e
Hong Chen 1, 2, 3, 4, 5 , Guillaume Noirbent 2, 5, 6, 7, 8 , Yijun Zhang 1, 2, 3, 4, 5 , Damien Brunel 2, 5, 6, 7, 8 , Didier Gigmes 2, 5, 6, 7, 8 , Fabrice Morlet-Savary 1, 2, 3, 4, 5 , Bernadette Graff 1, 2, 3, 4, 5 , Pu Xiao 9, 10, 11, 12 , Frédéric Dumur 2, 5, 6, 7, 8 , Jacques Lalevée 1, 2, 3, 4, 5
Affiliation  

A series of carbazole or triphenylamine based mono-chalcones, displaying either D–π-A or A–π-D–π-A architecture, have been designed and synthesized for intense absorption bands at around 405 nm with high molar extinction coefficients around 105 M−1 cm−1 corresponding to π–π* electronic transitions. Photosensitivity of the new photoinitiating systems composed of a chalcone and an iodonium salt (Iod) was investigated by UV-visible absorption and fluorescence spectroscopies, and their photoinitiation abilities were examined during the free radical polymerization of acrylates, whose polymerization kinetics were monitored by real-time Fourier Transform Infrared (RT-FTIR) spectroscopy upon irradiation with a LED@405 nm. In this work, a series of ten chalcones comprising a carbazole unit or a triphenylamine (TPA) group used as the electron donor for chalcones were specifically designed. Remarkably, nine of the proposed chalcones were never reported in the literature (never synthesized before). Only chalcone 7 was reported but only as a precursor for the design of pyrazolines for optical materials. As a result of this strategy, highly conjugated high-molecular-weight photoinitiators were obtained, displaying improved light absorption properties due to their extended polyaromaticity. These new photoinitiators offer new prospects for the design of novel and efficient photoinitiators. To evidence the interest of these new chalcones, 3D and 4D printing experiments were carried out with a polyethylene glycol (PEG)-diacrylate photosensitive resin comprising the best photoinitiating systems investigated. The shapes of 3D patterns can be reversibly modified by means of a thermal or hydrophilic response of PEG for a 4D activation.

中文翻译:

基于咔唑/三苯氨基基查耳酮的新型D-π-A和A-π-D-π-A三组分光引发体系及其在3D和4D打印中的应用

已经设计并合成了一系列基于咔唑或三苯胺的单查耳酮,它们显示出D–π-A或A–π-D–π-A结构,并在405 nm左右具有很强的吸收带,且摩尔消光系数大约为10 5 M -1厘米-1对应于π–π *电子跃迁。通过紫外可见吸收和荧光光谱研究了由查尔酮和碘鎓盐(Iod)组成的新光引发体系的光敏性,并在丙烯酸酯的自由基聚合过程中检测了它们的光引发能力,并通过实时监测其聚合动力学。 LED @ 405 nm照射后的时间傅立叶变换红外(RT-FTIR)光谱。在这项工作中,专门设计了一系列十个包含咔唑单元或三苯胺(TPA)基团的查耳酮,用作查耳酮的电子供体。值得注意的是,文献中从未报告过提出的九种查耳酮(以前从未合成过)。仅报告了查耳酮7,但仅作为光学材料吡唑啉设计的前体。作为该策略的结果,获得了高度共轭的高分子量光引发剂,由于其扩展的多芳族性而显示出改善的光吸收性能。这些新型的光引发剂为新型,高效的光引发剂的设计提供了新的前景。为了证明对这些新型查耳酮的兴趣,对包含研究的最佳光引发体系的聚乙二醇(PEG)-二丙烯酸酯光敏树脂进行了3D和4D打印实验。3D图案的形状可以通过PEG的热响应或亲水响应进行4D激活,从而可逆地修改。这些新型的光引发剂为新型,高效的光引发剂的设计提供了新的前景。为了证明对这些新型查耳酮的兴趣,对包含研究的最佳光引发体系的聚乙二醇(PEG)-二丙烯酸酯光敏树脂进行了3D和4D打印实验。3D图案的形状可以通过PEG的热或亲水响应进行4D激活而可逆地修改。这些新型的光引发剂为新型,高效的光引发剂的设计提供了新的前景。为了证明对这些新型查耳酮的兴趣,对包含研究的最佳光引发体系的聚乙二醇(PEG)-二丙烯酸酯光敏树脂进行了3D和4D打印实验。3D图案的形状可以通过PEG的热或亲水响应进行4D激活而可逆地修改。
更新日期:2020-09-24
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