N-Phthaloyltranexamic acid ammonium salt derivatives as photocaged superbase for redox free radical photopolymerization
N-Phthaloyltranexamic acid ammonium salt derivatives as photocaged superbase for redox free radical photopolymerization
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N-邻苯二甲酰氨甲环酸铵盐衍生物作为氧化还原自由基光聚合的光笼超强碱
DOI：
10.1039/c3py01448g
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发表时间：
2014-01-01
影响因子：
4.6
通讯作者：
Yang, Jianwen
中科院分区：
文献类型：
--
作者：
He, Minghui;Chen, Guangxue;Yang, Jianwen
N-邻苯二甲酰氨甲环酸铵盐衍生物与过氧化物结合可以引发氧化还原光聚合和传播聚合。合成并表征了一系列基于二苯甲酮、噻吨和石脑油发色团作为新型光笼碱的 N-邻苯二甲酰氨甲环酸铵盐衍生物。与过氧化苯甲酰引发剂结合，这些结构能够引发胺介导的丙烯酸酯的氧化还原光聚合。特别是，与母体化合物相比，N-邻苯二甲酰亚氨基氨基酸和II型发色团（噻吨酮、二苯甲酮）的共价结合显着提高了光笼碱（噻吨酮-DBU和二苯甲酮-DBU）的光反应性。此外，萘-DBU 与汞灯的发射光谱非常匹配，主发射波长为 365 nm。更重要的是，邻苯二甲酸酯-DBU和BPO作为一种新的光笼氧化还原组合可以在3分钟的照射时间内引发受控的氧化还原聚合。最后，由于产生的长效胺与过氧化物的持续相互作用，在氧化还原光聚合中初步实现了辐照后显着的后转化，这对于制备光屏蔽材料具有重要意义。
N-Phthaloyltranexamic acid ammonium salt derivatives integrating with peroxides can invoke redox photopolymerization and propagating polymerization. A series of N-phthaloyltranexamic acid ammonium salt derivatives based on benzophenone, thioxanthen, and naphtha chromophores as novel photocaged bases were synthesized and characterized. In combination with a benzoyl peroxide initiator, these structures were able to initiate the amine-mediated redox photopolymerization of acrylates. In particular, the covalent binding of N-phthalimidoamino acid and type II chromophores (thioxanthone, benzophenone) improved remarkably the photoreactivity of photocaged bases (thioxanthen-DBU and benzophenone-DBU) compared to the parent compound. Furthermore, naphthal-DBU matches well the emission spectra of the mercury lamp with a dominant emission wavelength at 365 nm. More importantly, phthal-DBU & BPO as a new photocaged redox combination can invoke controlled redox polymerization within an irradiation time of 3 min. Finally, due to the persistent interaction of the produced longeval amine with peroxides, remarkable post conversion after irradiation, which is significant for preparation of photo-screened materials, was thus initially achieved in the redox photopolymerization.