Molecular shape recognition-structure correlation in a phenylalanine-based polymer–silica composite by surface-initiated atom transfer radical polymerization
Molecular shape recognition-structure correlation in a phenylalanine-based polymer–silica composite by surface-initiated atom transfer radical polymerization
复制标题
DOI：
10.1016/j.polymer.2008.10.017
复制
发表时间：
2008-11
期刊：
影响因子：
4.6
通讯作者：
M. Czaun;Mohammed Mizanur Rahman;M. Takafuji;H. Ihara
中科院分区：
文献类型：
--
作者：
M. Czaun;Mohammed Mizanur Rahman;M. Takafuji;H. Ihara
合成并表征了一种可聚合的l-苯丙氨酸衍生单体N ' -十八烷基-N - α[4-（丙烯氧基）-丁醇基]-l-苯丙氨酸酰胺(3)。我们报道了一种先进的分子形状识别杂化材料的方法，包括将自由基引发剂固定在介孔二氧化硅颗粒（平均直径为4μm，孔径为12nm，表面积分别为300m2 - 1）上，并从接枝引发剂的颗粒中引发单体3的表面原子转移自由基聚合。所有样品采用元素分析、热重分析、漫反射红外傅立叶变换光谱、固态核磁共振（13C CP/MAS NMR和29si CP/MAS NMR）、差示扫描量热法和扫描电镜进行表征。采用反相高效液相色谱法（RP-HPLC）研究了聚合物-硅杂化材料对多环芳烃（PAHs）的分子形态识别能力。与传统RP-HPLC包装材料十八烷基硅烷固定相相比，该复合材料具有更好的平面选择性，与最近报道的聚（N ' -十八烷基-N - α-（4-乙烯基）-苯甲酰-l-苯丙胺）接枝二氧化硅相比，其线性选择性也有所提高。这种选择性的增强可归因于十八烷基链的疏水效应和固定相酰胺基之间的多重羰基π -苯π相互作用以及多环芳烃的离域电子的结合。
A polymerizable l-phenylalanine-derived monomer (N′-octadecyl-Nα[4-(acryloyloxy)-butanoyl]-l-phenylalanineamide (3)) has been newly synthesized and characterized. We reported an advanced approach to molecular shape recognitive hybrid materials that involves immobilization of radical initiator on mesoporous silica particles (average diameter, pore size and surface area are 4μm, 12nm, and 300m2g−1, respectively) and surface-initiated atom transfer radical polymerization of monomer 3 from initiator-grafted particles. All samples were characterized by elemental analysis, thermogravimetric analysis, diffuse reflectance infrared Fourier transform spectroscopy, solid state NMR measurements (13C CP/MAS NMR and29Si CP/MAS NMR), differential scanning calorimetry and scanning electron microscopy. The obtained polymer–silica hybrid material was used as a stationary phase for reversed-phase high performance liquid chromatography (RP-HPLC) to investigate its molecular shape recognition ability towards polycyclic aromatic hydrocarbons (PAHs). The new composite material showed better planarity selectivity than octadecylsilane stationary phase as a conventional RP-HPLC packing material and also enhanced linearity selectivity compared with the recently reported poly(N′-octadecyl-Nα-(4-vinyl)-benzoyl-l-phenylalanineamide)-grafted silica. Such selectivity enhancement can be attributed to the combination of hydrophobic effect due to octadecyl chains and multiply carbonyl π–benzene π interaction between the amide groups of the stationary phase and delocalized electrons of PAHs.