Butyl-bridged Double Schiff Base Compounds And Complexes Containing Quinoline Structural Unit Of The Synthesis And Properties Of Study

The Schiff base compounds represent one of the most widely utilized classes of ligand in coordination chemistry, which are well studied in the fields of organic synthesis and metal complexation. These ligands and their complexes find many important applications in chemical analysis, catalysis, medicine synthesis, etc. The derivatives of 8-hydroxyquinoline are widely used in the fields of chemistry, materials science, biology and medicinel fields. They not only can be used as extractant of metal ions, precipitation agent and fluorescence analysis reagent, but also can be used as a drug intermediate. Therefore, It is of great significance to synthesize Schiff base type 8-hydroxyquinoline derivatives and its complexes, and study the coordination and other properties. In this paper, five new Schiff base type 8-hydroxyquinoline derivatives and thirty related transition metal complexes were synthesized and characterized, and the study on their structure and properties was carred out, and some interesting results were obtained. The paper includes the following five sections:Chapter I:The importance of Schiff base type ligands and derivatives of 8-hydroxyquinoline in the field of analytical chemistry, coordination chemistry, materials chemistry, material science and medicine is described. The recent research related to the derivatives of the 8-hydroxyquinoline is reviewed.Chapter II:1,4-Bis(2-methyl-8-quinolyl)butane was prepared by using 2-methyl-8-hyd roxyquinoline and 1,4-Dibromobutane as the starting materials in base condition. Then,1, 4-bis(2-formyl-8-quinolyl)butane was obtained by the oxidation of 1,4-bis(2-methyl-8-quino lyl)butane with SeO2, These two products charactered by IR,1H NMR and x-ray single crystal diffraction.Chapter III:Five new Schiff base compounds were synthesized by the reaction of 1,4-bis(2-formyl-8-quinolyl)-butane and substituted anilines. The Schiff bases were charactered through IR and 1H NMR. The results show that the five new Shiff base compounds have absorptions in 1625-1612cm-1 in IR spectra, and chemical shifts in 8.49-8.69 ppm in 1H NMR spectra. These results are identical with the structures of the five Shiff base compounds.Chapter IV:Thirty kinds of the newly synthesized Schiff bases with transition meta (Cu, Co, Ni, Mn, Zn) chlorides, nitrates, sulfates were prepared. The characterization resu Its show that the Schiff bases coordinate to transition metals with 1:2 (ligand:metal) ra tio.In the IR spectra, the vibration frequencies of Schiff base C=N bonds decrease 7-20 cm-1, the vibration frequencies of priding rings decrease 13-49 cm-1, and the vibration fre quencies of the Ar-O-CH2 bonds increase 40-80 cm-1, after the Shiff bases coordinate to the transition metals. The vibration frequencies of M-N and M-O bonds are in range of 547-463 cm-1 and 490-432 cm-1 respectively. The changes indicate that the N atom in imi ne group, the N atom of the pyridine ring and the ether oxygen atom are invoved in co ordination. The x-ray single crystal structures of 1,4-bis(2-methyl-8-quinolineoxy)butane·C u(NO3)2, 1,4-bis[2-(4-fluorophenyl)iminomethyl-8-quinolinoxy]butane·CuCl2, 1,4-bis[2-(4-b romophenyl)iminomethyl-8-quinolinoxy]butane·CoCl2, and 1,4-bis[2-(4-bromophenyl)imin omethyl-8-quinolinoxy]butane·MnCl2 complexes were measured. The structures show that the complexes are binuclear complexes.Chapter V:The electrochemical property of Cu(II) complex of 1,4-bis[2-(4-fluorophe nyl)imino-methyl-8-quinolinoxy]butane was studied. Its redox potential (ORP)△E is 1.253 7V, which is higher than that of free Cu(II)/Cu(I) (△E=0.538V). The results mean that when the complexe is formed, it is difficult to undergoes redox reaction. Measure antib acterial activities of Co(II) and Mn(II) of 1,4-bis[2-(4-bromophenyl)iminomethyl-8-quinolin oxy]butane were also carried out. The results show that the antibacterial activity tests on E. Coil, B. Subtilis and Staphylococcus aureus of complexs were. The results indicate th atcomplexs used in the tests can inhibit the growth of E. Coil, B. Subtilis and Staphyloc occus aureus and the complexes exhibite higher biological activity compared with ligand.