5-[4-(2,3-环氧丙氧基)苯基]-10,15,20-三苯基卟啉的合成与表征

以丙酸和硝基苯为混合溶剂,苯甲醛、对羟基苯甲醛和吡咯为原料合成了5-对羟基苯基-10,15,20-三苯基卟啉(HPTPP).然后以HPTPP和环氧氯丙烷为原料,在NaOH催化条件下合成了5-4-(2,3-环氧丙氧基)苯基]-10,15,20-三苯基卟啉(EPPTPP).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HPTPP和EPPTPP的化学结构和光学性质进行了表征与测试.结果表明:FTIR谱图中,1 347cm-1和917cm-1处为EPPTPP卟啉环中C N键伸缩振动吸收峰和环氧化物环的(C—OC键)不对称伸缩振动吸收峰.EPPTPP的1 H NMR谱图中,在δ2.94～4.56内5个位移峰峰面积比为1∶1∶1∶1∶1,与EPPTPP中环氧基团的不同氢原子数比完全一致.UV-Vis谱图中,具有与卟啉结构相符合的吸收峰,表明成功合成了EPPTPP.通过荧光光谱分析了HPTPP和EPPTPP的荧光性质,并计算得到了二者的荧光量子产率分别为0.140和0.143.

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

5-p-Hydroxyphenyl-10,15,20-triphenylporphyrin(HPTPP) was synthesized by using benzaldehyde,p-hydroxybenzaldehyde and pyrrole as raw materials,propionic acid and nitrobenzene as solvent.5-4-(2,3-epoxypropoxy)phenyl]-10,15,20-triphenylporphyrin(EPPTPP) was prepared by using HPTPP and epichlorohydrin(ECH) as materials,sodium hydroxide as catalyst.The chemical structure and optical properties of HPTPP and EPPTPP were characterized and tested by Fourier transform infrared spectrometer(FTIR),nuclear magnetic resonance spectrometer(NMR),ultraviolet-visible(UV-Vis) spectrophotometer and spectrofluorophotometer,respectively.The results showed that absorption peaks at 1 347 cm-1 and 917 cm-1 were attributed to C=N bond stretching vibration peaks of EPPTPP porphyrin ring and C—O—C bond asymmetric stretching vibration absorption peak of epoxide ring in FTIR spectra.In 1H NMR spectrum of EPPTPP,the peak area ratio of 5 chemical shift peaks was 1∶1∶1∶1∶1 between 2.94 to 4.56,which was consistent with the ratio of the hydrogen atom number of epoxy group.The absorption peaks of EPPTPP were similar to those of porphyrin in UV-Vis spectrum,which confirmed that EPPTPP had been successfully synthesized.The fluorescence properties of HPTPP and EPPTPP were analyzed by fluorescence spectroscopy and fluorescence quantum yield were 0.140 and 0.143,respectively.