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Water-soluble bis-chalcone-based photoinitiators with long-wavelength absorption for radical polymerization and 3D printing
Polymer Chemistry ( IF 4.1 ) Pub Date : 2024-01-31 , DOI: 10.1039/d4py00023d Weineng Lu 1 , Jinqing Qu 1
Polymer Chemistry ( IF 4.1 ) Pub Date : 2024-01-31 , DOI: 10.1039/d4py00023d Weineng Lu 1 , Jinqing Qu 1
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Two water-soluble bis-chalcone-based photoinitiators 4,4′-((((1E,1′E)-(2-oxocyclopentane-1,3-diylidene)bis(methaneylylidene))bis(thiophene-5,2-diyl))bis(9H-carbazole-3,9-diyl))bis(butane-1-sulfonic acid) (KSES) and 4,4′-((((1E,1′E)-(2-oxocyclohexane-1,3-diylidene)bis(methaneylylidene))bis(thiophene-5,2-diyl))bis(9H-carbazole-3,9-diyl))bis(butane-1-sulfonic acid) (KSTS) were successfully synthesized. The maximum absorption wavelengths (λmax) of KSES and KSTS in water were 514 and 469 nm, respectively. KSES and KSTS could be combined with diphenyliodonium hexafluorophosphate (Iod) and triethanolamine (TEOA) to form a three-component photoinitiation system, which could quickly trigger the curing of acrylate coatings under visible light with a final C![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
C bond conversion of more than 98%. The high free radical polymerization efficiency also made the bis-chalcone/Iod/TEOA system suitable for 3D printing, successfully printing clear and photobleached 3D objects. In addition, we carried out photosteady-state degradation, fluorescence quenching and ESR-ST experiments to further study the photopolymerization mechanism. Besides, KSES and KSTS also exhibited good biocompatibility, photobleaching performance and extremely low mobility. Considering the above excellent performance, the two water-soluble bis-chalcone-based photoinitiators reported in this study are very good choices for visible light polymerization in water-soluble systems.
中文翻译：
具有长波长吸收功能的水溶性双查尔酮光引发剂，用于自由基聚合和 3D 打印
两种水溶性双查耳酮光引发剂 4,4′-((((1 E ,1′ E )-(2-氧代环戊烷-1,3-二亚基)双(亚甲基亚基))双(噻吩-5,2 -二基))双(9 H -咔唑-3,9-二基))双(1-丁烷-磺酸) (KSES) 和 4,4′-((((1 E ,1′ E )-(2 -氧代环己烷-1,3-二亚基)双(亚甲基))双(噻吩-5,2-二基))双(9 H-咔唑-3,9-二基))双(丁烷-1-磺酸) (KSTS ) 已成功合成。KSES和KSTS在水中的最大吸收波长( λ max )分别为514和469 nm。KSES和KSTS可以与六氟磷酸二苯基碘(IOD)和三乙醇胺(TEOA)组合形成三组分光引发体系，在可见光下快速引发丙烯酸酯涂料固化，最终C C键转化率超过98% 。高自由基聚合效率也使得双查耳酮/Iod/TEOA体系适合3D打印，成功打印出透明且光漂白的3D物体。此外，我们还进行了光稳态降解、荧光猝灭和ESR-ST实验来进一步研究光聚合机理。此外，KSES和KSTS还表现出良好的生物相容性、光漂白性能和极低的迁移率。考虑到上述优异的性能，本研究报告的两种水溶性双查尔酮基光引发剂是水溶性体系中可见光聚合的非常好的选择。
更新日期：2024-01-31
C bond conversion of more than 98%. The high free radical polymerization efficiency also made the bis-chalcone/Iod/TEOA system suitable for 3D printing, successfully printing clear and photobleached 3D objects. In addition, we carried out photosteady-state degradation, fluorescence quenching and ESR-ST experiments to further study the photopolymerization mechanism. Besides, KSES and KSTS also exhibited good biocompatibility, photobleaching performance and extremely low mobility. Considering the above excellent performance, the two water-soluble bis-chalcone-based photoinitiators reported in this study are very good choices for visible light polymerization in water-soluble systems.
中文翻译：
具有长波长吸收功能的水溶性双查尔酮光引发剂，用于自由基聚合和 3D 打印
两种水溶性双查耳酮光引发剂 4,4′-((((1 E ,1′ E )-(2-氧代环戊烷-1,3-二亚基)双(亚甲基亚基))双(噻吩-5,2 -二基))双(9 H -咔唑-3,9-二基))双(1-丁烷-磺酸) (KSES) 和 4,4′-((((1 E ,1′ E )-(2 -氧代环己烷-1,3-二亚基)双(亚甲基))双(噻吩-5,2-二基))双(9 H-咔唑-3,9-二基))双(丁烷-1-磺酸) (KSTS ) 已成功合成。KSES和KSTS在水中的最大吸收波长( λ max )分别为514和469 nm。KSES和KSTS可以与六氟磷酸二苯基碘(IOD)和三乙醇胺(TEOA)组合形成三组分光引发体系，在可见光下快速引发丙烯酸酯涂料固化，最终C C
键转化率超过98% 。高自由基聚合效率也使得双查耳酮/Iod/TEOA体系适合3D打印，成功打印出透明且光漂白的3D物体。此外，我们还进行了光稳态降解、荧光猝灭和ESR-ST实验来进一步研究光聚合机理。此外，KSES和KSTS还表现出良好的生物相容性、光漂白性能和极低的迁移率。考虑到上述优异的性能，本研究报告的两种水溶性双查尔酮基光引发剂是水溶性体系中可见光聚合的非常好的选择。
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