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Novel bis-chalcone-based carbazole derivative photoinitiators for visible light polymerization with good photobleaching and biocompatibility
Progress in Organic Coatings ( IF 6.5 ) Pub Date : 2023-11-28 , DOI: 10.1016/j.porgcoat.2023.108102
Weineng Lu , Guanhao Ma , Jinqing Qu

Four novel bis-chalcone-based carbazole derivative photoinitiators (2E,5E)-2,5-bis((9-phenyl-9H-carbazol-3-yl)methylene)cyclopentan-1-one (KZA), 2,5-bis((E)-4-(9H-carbazol-9-yl)benzylidene)cyclopentan-1-one (KZB), (2E,5E)-2,5-bis((9-ethyl-9H-carbazol-3-yl)methylene)cyclopentan-1-one (KZC) and (2E,5E)-2,5-bis((5-(9-ethyl-9H-carbazol-3-yl)thiophen-2-yl)methylene)cyclopentan-1-one (KZD) were successfully designed and synthesized. Their maximum absorption wavelengths were 440 nm, 405 nm, 446 nm and 500 nm, respectively, and they all had high molar extinction coefficients. Furthermore, three-component photoinitiation system including bis-chalcone/iodonium/amine could quickly and efficiently trigger the photopolymerization of acrylates. For example, PEGDA coatings could cure in 10 s and the Cdouble bondC bond conversion exceeded 90 % in the end. Then we also conducted photosteady-state degradation, fluorescence quenching, cyclic voltammetry and ESR experiments to investigate the mechanisms of photopolymerization. Besides, all four bis-chalcones showed good photobleaching and biocompatibility, which was suitable for use in 3D printing and deep coating curing. For instance, the LCD 3D printer successfully printed clear and photobleached objects with KZD/iodonium/amine system. All these excellent properties indicated the industrial application potential of the four carbazole derivatives in visible light curing.



中文翻译:

新型双查尔酮基咔唑衍生物光引发剂,用于可见光聚合,具有良好的光漂白性和生物相容性

四种新型双查尔酮基咔唑衍生物光引发剂 (2E,5E)-2,5-双((9-苯基-9H-咔唑-3-基)亚甲基)环戊烷-1-酮 (KZA), 2,5-双((E)-4-(9H-咔唑-9-基)亚苄基)环戊烷-1-酮(KZB),(2E,5E)-2,5-双((9-乙基-9H-咔唑-3) -基)亚甲基)环戊烷-1-酮(KZC)和(2E,5E)-2,5-双((5-(9-乙基-9H-咔唑-3-基)噻吩-2-基)亚甲基)环戊烷-1-酮(KZD)的设计和合成成功。它们的最大吸收波长分别为440 nm、405 nm、446 nm和500 nm,并且都具有高摩尔消光系数。此外,双查耳酮/碘鎓/胺三组分光引发体系可以快速有效地引发丙烯酸酯的光聚合。例如,PEGDA涂层可以在10秒内固化,双键最终CC键转化率超过90%。然后我们还进行了光稳态降解、荧光猝灭、循环伏安和ESR实验来研究光聚合机理。此外,四种双查尔酮均表现出良好的光漂白性和生物相容性,适合用于3D打印和深层涂层固化。例如,LCD 3D打印机使用KZD/碘/胺系统成功打印了透明和光漂白的物体。这些优异的性能表明了四种咔唑衍生物在可见光固化方面的工业应用潜力。

更新日期:2023-11-28
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