2-(2,5-二羟苯基)四苯基卟啉及其金属配合物的合成与表征  

Synthesis of 2-(2,5-Dihydroxyphenyl)-Tetraphenylporphrin and Its Structure Identification

作　　者：陈世清[1] 陈彰评[1] 黄齐茂[1] 姜中兴[1] 

机构地区：[1]武汉大学化学与分子科学学院,湖北武汉430072

出　　处：《光谱学与光谱分析》2004年第6期713-716,共4页Spectroscopy and Spectral Analysis

基　　金：国家自然科学基金(29872 0 33)资助项目

摘　　要：对苯二酚与 2 硝基 5 ,10 ,15 ,2 0 四苯基卟啉 1及其铜 (Ⅱ ) 2、镍 (Ⅱ ) 3、锌 (Ⅱ ) 4等金属配合物直接加热反应 ,分别制得 2 (2 ,5 二羟苯基 )四苯基卟啉 1′(81% )及相应金属配合物 2′(71% ) ,3′(6 1% ) ,4′(40 % )。它们的结构由IR ,MS ,UV及1 HNMR ,2D NMR等确定。发现对苯二酚通过碳 碳键与卟啉的吡咯环直接相连 ,氢醌与卟啉环趋于共平面 ,其中一个羟基位于卟啉环的去屏蔽区 ,H原子的核磁位移向低场移动 (δ =7 5 2 ) ,另一个则处于中位苯环的屏蔽区 ,H原子的核磁位移为δ =4 18;氢醌环上的质子也表现出不同的核磁位移 ,其中 6位上H的位移值为δ =4 93,明显向高场位移。2-(2,5-dihydroxyphenyl)-tetraphenylporphrin 1', 2-(2,5-dihydroxyphenyl)-tetraphenylporphyrinato Cu(II)2', Ni(II)3' and Zn(II)4' were synthesized by direct reaction of 2-nitro-5,10,15, 20-tetraphenylporphrin 1 or its metallic complexes 2, 3, 4 with hydroquinone under heating without solvent. The yields were about 81%, 71%, 61% and 40% respectively for 1', 2', 3' and 4'. Their structures were determined by H-1 NMR, 2D NMR, IR, MS and UV-Vis spectra. It is shown that the hydroquinone connects with pyrrole ring through carbon-carbon bond, and is located in the same plane of porphyrin. One of the hydroxy group of hydroquinone is located in the deshield area of porphyrin and its proton shift occurs downfield at delta = 7.52. Another one is located in the shield area of meso benzene, and the proton shift occurs upfield at delta = 4.18. Also the 6 proton shift of hydroquinone occurs upfield at delta = 4.93.

关 键 词：2-(2 5-二羟苯基)四苯基卟啉 铜配合物 镍配合物 锌配合物 合成 结构表征 

分 类 号：O626.13[理学—有机化学] O641.4[理学—化学]