Bis-chalcone derivatives derived from natural products as near-UV/visible light sensitive photoinitiators for 3D/4D printing,Materials Chemistry Frontiers

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Bis-chalcone derivatives derived from natural products as near-UV/visible light sensitive photoinitiators for 3D/4D printing
Materials Chemistry Frontiers ( IF 6.0 ) Pub Date : 2020-10-29 , DOI: 10.1039/d0qm00755b
Hong Chen _{1,

2,

3,

3,

4} , Guillaume Noirbent _{3,

5,

6} , Shaohui Liu _{1,

2,

3,

3,

4} , Damien Brunel _{3,

5,

6} , Bernadette Graff _{1,

2,

3,

3,

4} , Didier Gigmes _{3,

5,

6} , Yijun Zhang _{1,

2,

3,

3,

4} , Ke Sun _{1,

2,

3,

3,

4} , Fabrice Morlet-Savary _{1,

2,

3,

3,

4} , Pu Xiao _{7,

8,

9} , Frédéric Dumur _{3,

5,

6} , Jacques Lalevée _{1,

2,

3,

3,

4}

Affiliation

Four series of bis-chalcone compounds based on benzylpiperidinone, tetrahydrothiopyranone, pyridine or biphenyl central parts are designed and synthesized, enabling the development of ten bis-chalcones varying both by the central cores and by the substitution patterns (ortho, meta, para-positions) and the choice of the different groups attached to the peripheral substituents (alkoxy or allyloxy-substituted aromatic rings, thiophene, or ferrocene). In this series of ten bis-chalcones, eight of them were never synthesized before (i.e. only bis-chalcones 8 and 10 were already reported albeit never used as photoinitiators). These different dyes are proposed as new near-UV/visible light sensitive photoinitiators, in combination with an amine and an iodonium salt, to initiate the free radical photopolymerization (FRP) of PEG-diacrylate and the cationic photopolymerization (CP) of EPOX under LED@405 nm and LED@375 nm irradiation conditions. For the photopolymerization of acrylates carried out between thin films in laminate, all the bis-chalcones proposed in this work show higher photoinitiation abilities upon irradiation with a LED at 375 nm than at 405 nm, which is mainly due to their excellent light absorption properties in the near-UV region. Markedly, in contrast with the other two series of bis-chalcone compounds, pyridine-based bis-chalcones prove to be the most efficient photoinitiators, especially the bis-chalcones 5 and 9. Furthermore, all of them can also promote the cationic polymerization of epoxides upon LED irradiation at 375 nm, in the presence of an iodonium salt and an amine. More interestingly, some 3D patterns fabricated through the free radical polymerization of PEG-diacrylate demonstrate reversible swelling properties and shape-memory for access to 4D printing.

中文翻译：

来自天然产物的双查尔酮衍生物，用作3D / 4D打印的近紫外/可见光敏光引发剂

设计并合成了基于苄基哌啶酮，四氢硫代吡喃酮，吡啶或联苯中心部分的四系列双查耳酮化合物，可开发出十个双查耳酮，其中心核心和取代方式都不同（邻位，间位，对位）以及与外围取代基（烷氧基或烯丙氧基取代的芳环，噻吩或二茂铁）相连的不同基团的选择。在这一系列的十个双查耳酮中，其中八个从未被合成过（即仅双查耳酮8和10已被报道，尽管从未用作光引发剂）。提议将这些不同的染料作为新型近紫外/可见光敏光引发剂，与胺和碘鎓盐组合使用，以引发PEG-二丙烯酸酯的自由基光聚合（FRP）和LED下EPOX的阳离子光聚合（CP）。 @ 405 nm和LED @ 375 nm的照射条件。对于丙烯酸酯的光聚合，在层压板的薄膜之间进行，这项工作中提出的所有双查耳酮在375 nm的LED照射下均比在405 nm的情况下显示出更高的光引发能力，这主要是由于它们在470 nm时具有出色的光吸收性能。近紫外线区域。明显地，与其他两个系列的双查尔酮化合物相比，吡啶基的双查尔酮被证明是最有效的光引发剂，5和9。此外，它们都可以在碘鎓盐和胺的存在下在375 nm的LED照射下促进环氧化物的阳离子聚合。更有趣的是，通过PEG-二丙烯酸酯的自由基聚合制备的一些3D图案显示出可逆的溶胀特性和形状记忆，可用于4D打印。

更新日期：2020-11-23

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