摘要
分别以3-硝基邻苯二甲酸和4-硝基邻苯二甲酰亚胺为前体,经过三步反应,制备了两类水溶性酞菁铁衍生物1,8,15,22-四(3'-羧基丙酰胺基)酞菁铁(a3)和2,9,16,23-四(3'-羧基丙酰胺基)酞菁铁(b3),并用FT-IR,UV-Vis对其结构进行了表征.测定了a3,b3在DMSO以及在不同pH值NaOH水溶液中的溶解度.a3,b3的摩尔消光系数在不同pH值的NaOH溶液中近似为一个定值,溶解度随NaOH溶液碱性增强而增加.对a3,b3与不同位置取代的四硝基、四氨基酞菁铁在DMF、DMSO、吡啶中的紫外-可见吸收光谱进行了比较分析.讨论了取代基位置对酞菁溶解性的影响,a3分子中酰胺键上的氢与酞菁环相邻的氮原子形成分子内氢键导致其溶解度降低,使得其在DMSO和相同pH值的NaOH溶液中的溶解度比b3要小.在相同pH值的NaOH溶液中b3的溶解度大约为a3的2-3倍.
Two kinds of water-soluble phthalocyanine iron derivatives, 1,8,15,22-tetra - 3＇ - carboxylpropionamide phthalocyanine iron （ III ） and 2,9,16,23 - tetra - 3＇ - carboxylpropionamide phthalocyanine iron （III） complexes （ a3 and b3） were prepared in three steps from 3 - nitrophthalie and 4 - nitrophthalimide, respectively. Phthalocyanine iron complexes were characterized by FT-IR and UV-vis. The solubility of a3 and b3 in DMSO and NaOH solution were determined. The absorption spectra of a3 and b3 and their molar extinction coefficient at Q-band, however, did not change with pH of NaOH solution. Solubility of a3 and b3 in NaOH solution increased with pH. UV-vis spectra of a3 and b3, tetra-nitrophthalocyanine iron and tetra-aminophthaloeyanine iron in DMSO,DMF and Py were compared. The effects of substituent at different positions on their solubility in DMSO and Water were discussed. Compared with b3, the solubility of 8-3 in DMSO and the same pH value NaOH solution was lower, which may be attributed to the formation of intramoleeular H-bonds between H atom of amide-group and the adjacent N atom in Pc ring. In the same pH value NaOH solution, the solubility of b3 was about 2 -3 times as much as that of a3.
出处
《西华师范大学学报（自然科学版）》
2012年第2期161-169,共9页
Journal of China West Normal University(Natural Sciences)
基金
化学合成与污染控制四川省重点实验开放基金(10CSPC-(1-7))资助项目
