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首页> 外文期刊>RSC Advances >Synthesis, characterization, and computational study of potential itaconimide-based initiators for atom transfer radical polymerization
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Synthesis, characterization, and computational study of potential itaconimide-based initiators for atom transfer radical polymerization

机译：潜在的基于itaconimide的原子转移自由基聚合引发剂的合成，表征和计算研究

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Atom transfer radical polymerization (ATRP) has been a promising technique to provide polymers with well-defined composition, architecture, and functionality. In most of the ATRP processes, alkyl halides are used as an initiator. We report the synthesis of three possible potential initiators, N-phenyl(3-bromo-3-methyl) succinimide, N-phenyl(3-bromo-4-methyl) succinimide, and N-phenyl(3-bromomethyl) succinimide for ATRP of N-phenylitaconimide (PI) and methyl methacrylate (MMA). These functionalized alkyl halides, having structural similarity with PI, were characterized by FTIR, HRMS, H-1, C-13 NMR spectroscopy, and elemental analysis. The equilibrium constants for the ATRP activation/deactivation process (K-ATRP) of these alkyl halides as well as a commercial ATRP initiator (ethyl-alpha-bromoisobutyrate) were determined using UV-Vis-NIR and DOSY NMR spectroscopy. Alternatively, these compounds and similar alkyl halides (R-X) were investigated using density functional theory for their possible chain initiation activity for the ATRP process. The B3LYP functional and 6-31+G(d)/LanL2DZ basis set was used for the prediction of geometries and energetics associated with the homolytic R-X bond dissociation. The relative value of K-ATRP and its variation with system parameters (such as substituent, temperature, and solvent) was investigated. We found a good agreement between the experimentally determined and theoretically calculated K-ATRP values. Our experiments show that the newly synthesized initiator N-phenyl(3-bromo-3- methyl) succinimide performs better than the commercially available initiator ethyl-alpha-bromoisobutyrate for the atom transfer radical copolymerization of PI and MMA.
机译：原子转移自由基聚合（ATRP）是一种有前途的技术，可为聚合物提供定义明确的组成，结构和功能。在大多数ATRP工艺中，卤代烷被用作引发剂。我们报告了三种可能的引发剂，ATRP的N-苯基（3-溴-3-甲基）琥珀酰亚胺，N-苯基（3-溴-4-甲基）琥珀酰亚胺和N-苯基（3-溴甲基）琥珀酰亚胺的合成N-苯基衣康酰亚胺（PI）和甲基丙烯酸甲酯（MMA）。通过FTIR，HRMS，H-1，C-13 NMR光谱和元素分析对与PI具有结构相似性的这些官能化烷基卤化物进行了表征。使用UV-Vis-NIR和DOSY NMR光谱法测定这些烷基卤化物以及商业ATRP引发剂（乙基-α-溴代异丁酸酯）的ATRP活化/失活过程（K-ATRP）的平衡常数。或者，使用密度泛函理论研究了这些化合物和类似的烷基卤化物（R-X）对于ATRP过程的可能的链引发活性。 B3LYP功能和6-31 + G（d）/ LanL2DZ基础集用于预测与均溶R-X键解离有关的几何形状和高能学。研究了K-ATRP的相对值及其随系统参数（例如取代基，温度和溶剂）的变化。我们在实验确定的值和理论计算的K-ATRP值之间找到了很好的一致性。我们的实验表明，对于PI和MMA的原子转移自由基共聚，新合成的引发剂N-苯基（3-溴-3-甲基）琥珀酰亚胺的性能优于市售引发剂乙基-α-溴异丁酸酯。

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