European Polymer Journal ( IF 5.8 ) Pub Date : 2022-04-20 , DOI: 10.1016/j.eurpolymj.2022.111198 Xiang Xu 1 , Yi Shen 1 , Yue Shu 1 , Yong Guan 1 , Dafu Wei 1
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Blue light hazards have garnered increasing attention owing to the popularity of displays. Although melanin on the retina acts as a blue light barrier, overexposure to blue light increases the risk of visual damage. A class of methyl indole-n-carboxylate oligomers (O-MInC, n = 3, 4, 5, 6, and 7) was synthesized through solid-phase oxidative polymerization. Based on the experimental characterizations, including time-of-flight mass spectrometry, infrared spectroscopy, and density functional theory calculations of the average local ionization energy, we proposed a mechanism for the oxidative polymerization of methyl indole-4-carboxylate (MI4C). Methyl indole-4-carboxylate oligomer (O-MI4C) is composed of cyclic oligomers containing large conjugated structures that are generated by the repetition of electron deprivation, radical coupling, and dehydrogenation reactions. O-MI4C exhibits the best blue light absorption among its allotropes substituted at different positions with a cut-off absorption wavelength of 530 nm. Finally, O-MI4C was added to polymethylmethacrylate (PMMA) and Columbia resin 39 (CR-39) flakes through in situ polymerization to investigate the behavior of blue light blocking. The PMMA/O-MI4C (0.01 wt%) and CR-39/O-MI4C (0.02 wt%) can block 25% and 35% of blue light; however, they have no significant effect on green and orange lights.
中文翻译:
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具有蓝光阻隔性能的聚吲哚-4-羧酸甲酯的合成与应用
由于显示器的普及,蓝光危害已引起越来越多的关注。虽然视网膜上的黑色素起到蓝光屏障的作用,但过度暴露于蓝光会增加视觉损伤的风险。一类甲基吲哚-n-羧酸低聚物(O-MI n C, n = 3、4、5、6 和 7) 通过固相氧化聚合合成。基于飞行时间质谱、红外光谱和平均局部电离能的密度泛函理论计算等实验表征,我们提出了吲哚-4-羧酸甲酯(MI4C)氧化聚合的机理。吲哚-4-羧酸甲酯低聚物 (O-MI4C) 由含有大共轭结构的环状低聚物组成,这些结构是通过重复电子剥夺、自由基偶联和脱氢反应产生的。O-MI4C在其不同位置取代的同素异形体中表现出最好的蓝光吸收,截止吸收波长为530 nm。最后,通过原位聚合将 O-MI4C 添加到聚甲基丙烯酸甲酯 (PMMA) 和哥伦比亚树脂 39 (CR-39) 薄片中,以研究蓝光阻挡行为。PMMA/O-MI4C(0.01 wt%)和CR-39/O-MI4C(0.02 wt%)可以阻挡25%和35%的蓝光;但是,它们对绿色和橙色光没有显着影响。