多位点硝基取代四苯基卟啉的合成及光谱研究

Synthesis and spectral research of multi-site substituted nitro groups of tetraphenylporphyrin

将硝基修饰于四苯基卟啉meso位苯环的邻、间、对位上,合成了三个化合物o-TNPP、m-TNPP及p-TNPP。考察了不同取代位点的硝基对卟吩环上电子云密度分布的影响。通过溶剂化效应、AIE效应、pH效应、循环伏安曲线测试表明,o-TNPP、p-TNPP的卟吩环内电子云密度减小,共轭增强,表现出ACQ性质。m-TNPP的meso位苯环上电子云呈螺旋桨式分布于硝基外围,使卟啉发生空间扭曲,共轭削弱,表现出AIE性质。

Three compounds o-TNPP,m-TNPP and p-TNPP are synthesized by modifying the nitro group in the ortho,meta and para-positions of the tetrazoporphyrin meso benzene ring.The effects of nitro groups at different substitution sites on the electron cloud density distribution on the porphin ring are investigated.Tested by solvation effect,AIE effect,pH effect,cyclic voltammetry curve show that the electron cloud density in the porphin ring of o-TNPP and p-TNPP is reduced,the conjugate is enhanced and the ACQ property is exhibited.The electron cloud on the benzene ring of the meso-position of m-TNPP is distributed in the propeller pattern on the periphery of the nitro group,which causes the space of the porphyrin to be distorted and the conjugate is weakened,showing the AIE property.