Synthesis Of Substituted Benzoyl Hydrazone Schiff Base And Properties Of Schiff Base

Imidazole compounds has been widely applied in fields of medicine,catalysis,analysis and so on, which can coordination with metal. Schiff base can be active in the field of coordination chemistry for the lively functional groups -C=N- and other diversity substituted functional groups, most of its metal complexes have features of high biological activity and low toxicity,also can be used as catalyst,schiff base has a promising future in application. The molecular recognition is a process that the host (receptor) produces selectively binding and a specific function on the guest (substrate). Schiff base and its derivatives have a good recognition effect on ions, thus, these compounds have attached more and more researchers’attention.More than thirty kinds of compounds including twenty new compounds were synthesized and studied in this thesis, which were characterized by 1H NMR,13C NMR, Elemental analysis and IR. Then, The synthesis of benzimidazole schiff base, phenanthrene imidazole schiff base and schiff base Cu(Ⅱ)-metal porphyrin is the main object in the job. At the same time, the spectral properties of some compounds are studied. This work includes the three aspects as follows.(1) Synthesis and characterization of benzimidazole hydrazone Schiff base. Benzimidazole acyhydrazone schiff base were synthesized from the raw material of o-phenylenediamine and 4-formylbenzoate, A series of benzimidazole acylhydrazones schiff bases including ten new compounds were prepared from the reaction procedure of cyclization, hydrazide, condensation. The fluorescence spectrophotometer showed that benzimidazole salicylaldehyde schiff bases has a certain ability to recognize Sn2+ and Al3+. P-formylbenzo formaldehyde schiff base and m-formylphenoxy formaldehyde schiff base have ability to recognize Cu2+. Salicylaldehyde benzimidazole schiff bases ligand with Zn2+, Ni2+ in molar rate of 2:1,1:1 by UV-visible spectrophotometer complexation titration, and the complexation constants were 7.92×105L/mol,1.13×105L/mol.(2) Synthesis and characterization of phenanthrene imidazole hydrazone schiff base. Phenanthrene imidazole hydrazone schiff base was synthesized from the raw material of 9,10-Phenanthrenequinone and p-formylbenzoate, A series of phenanthrene imidazole hydrazone schiff base including ten new compounds were prepared from the reaction procedure of cyclization, hydrazide, condensation.(3) Cu(Ⅱ) meso-tetra(schiff-base substituted phenyl)porphyrins were synthesized by using microwave. The experimental results showed that the condensation reaction rates and yields between substituted benzaldehyde and Cu(Ⅱ) Meso-5,10,15,20-tetrakis (4-aminophenyl) porphyrin related to the species of substituents, electron withdrawing group higher than electron donating group, increasing with the enhancement of electron withdrawing group and reducing with the enhancement of electron donating group. Cu-ligand could be formed between salicylaldehyde-schiff base copper metalloporphyrin and copper ions in alkaline conditions, the conversion and the selectivity of cyclohexanone reached 7.68% and 60.87% in catalytic oxidation of cyclohexane.