Complexes Of Tailed Porphyrin And Alkyl Ammonium Ion: Synthesis,Characterization And Properties

In this study,I designed porphyrin as host groups,ethoxy chain as binding site,and the introduction of amino porphyrin and ion distribution center in ethoxy chain end to form host molecule.Controlling the molecular configuration by the length of ethoxy chain,to study the selective role of the guest molecules,three sensing molecule(6a,6b,6c)were designed and synthesized.Porphyrin ring was synthesized by hydroxyl benzaldehyde,benzaldehyde and pyrrole in propionic acid under reflux.Target molecules were synthesized by condensation of porphyrin and phthalimide chloride.Target compounds and their intermediates were conformed by 1H NMR,MS,HSQC and COSY spectra.Due to the chemical shift of hydrogen atoms on amino and ethoxy chain has different degrees of high field displacement which means amino coordinate with the center ion and affected by the porphyrin ring current.Meanwhile,combined with coupling signal of two-dimensional nuclear magnetic and the relative abundance of the mass spectrometry for target molecules,I judged the target molecules are mainly existed in the form of monomer,and the content of dimer is negligible.The effect of di-hexylamine hydrochloride,di-hexylamine phosphate and di-hexylamine borate and other guest molecules with target molecular by nuclear magnetic titration and uv titration experiments.The results show that di-hexylamine borate has a strong combining capacity with the target molecules,and their bonding strength increase as ion pairing weaking(TFPB-(29)PF6-(29)Cl-).It may be the matching of host molecular configuration with shape of the guest molecules.