5,10,15,20-四[4-(2,3-环氧丙氧基)苯基]卟啉的合成与表征  

Synthesis and characterization of 5,10,15,20-tetra[4-(2,3-epoxypropoxy)phenyl]porphyrin

作　　者：王苗苗[1] 刘耀军[1] 王园[1] 王耀辉[1] 赵洪池[1] 

机构地区：[1]河北大学化学与环境科学学院,河北保定071002

出　　处：《河北大学学报（自然科学版）》2015年第1期48-53,共6页Journal of Hebei University(Natural Science Edition)

基　　金：国家自然科学基金资助项目(21474026);河北省自然科学基金资助项目(B2013201174)

摘　　要：以正丙酸、冰乙酸和硝基苯为混合溶剂，以对羟基苯甲醛和吡咯为原料，合成了5，10，15，20-四（4-羟基苯基）卟啉（THPP）．然后以THPP与环氧氯丙烷为原料，在异丙醇中以氢氧化钠为催化剂合成了5，1O，15，20-四[4-（2，3-环氧丙氧基）苯基]卟啉（TEPPP）．利用傅里叶变换红外光谱仪（FTIR）、核磁共振波谱仪（NMR）、紫外可见分光光度计（UV-Vis）和荧光分光光度计分别对THPP和TEPPP的化学结构和光学性质进行了表征与测试．结果表明：1349cm^-1和916cm^-1处为TEPPP卟啉环中C-N键伸缩振动吸收峰和环氧化物环的（C-O-C键）不对称伸缩振动吸收峰．TEPPP的1HNMR谱图中，在艿2.92～4.6O内5个位移峰峰面积比为1：1：1：1：1，与TEPPP中环氧基团的不同氢原子数比相一致．TEPPP的UV-Vis谱图具有与卟啉结构相符合的吸收峰．通过荧光光谱研究了THPP和TEPPP的荧光性质，并计算得到了二者的荧光量子产率分别为O.08和0.16.5, 10, 15, 20-tetra （4-hydroxylphenyl） porphyrin （THPP） was synthesized by using p- hydroxybenzaldehyde and pyrrole as raw materials, propionic acid, acetic acid and nitrobenzene as solvent. 5,10,15,20-tetraS4-（2,3-epoxypropoxy） phenyl porphyrin （TEPPP） was prepared by using THPP and epichlorohydrin as materials in isopropanol with sodium hydroxide as catalyst. The chemical structure and optical properties of THPP and TEPPP were characterized and tested by Fourier transform infrared spec- trometer （FTIR）, nuclear magnetic resonance spectrometer （NMR）, ultraviolet-visible （UV-Vis） spectro- photometer and spectrofluorophotometer, respectively. The absorption peaks at 1 349 cm^2 and 916 cm were attributed to C= N bond stretching vibration absorption peaks of TEPPP porphyrin ring and C -- O-- C bond asymmetric stretching vibration absorption peak of epoxide ring in FTIR spectrum of TEPPP, respectively. InCH NMR spectrum of TEPPP, the peak area ratio of 5 chemical shift peaks was 1：1：1：1：1 between 2.92 to 4.60, which was consistent with the ratio of the hydrogen atom number of epoxy group. The absorption peaks of TEPPP were similar to those of porphyrin in UV-Vis spectrum. The fluorescence properties of THPP and TEPPP were studied by fluorescence spectroscopy and fluorescence quantum yield were 0.08 and 0.16, respectively.

关 键 词：卟啉 5 1O 15 20-四[4-(2 3一环氧丙氧基)苯基]卟啉 紫外可见光谱 荧光光谱 荧光量子产率 

分 类 号：O631.5[理学—高分子化学]