Study Of Star-shaped Phenyl Thioether Compounds

Star-shaped phenyl thioether compounds consist of benzene and sulfur atoms alternately linking in shape of star. The structure of the persulfurated phenyl compound is intriguing with delicate well-define structure (three dimensional size, regular molecular weight, multi-sited functional groups). To structure of phenyl thioether, benzene ring provides rigidity and sulfur atoms provide a certain amount of flexibility. And the lone pairs of electron on the sulfur atom have a conjugate effect with π bond on the benzene ring, as the sulfur atom with lone pairs of electrons can stable positive or negative charges, so the combination of the special structure endow compound unique properties. The six-arm star-shaped phenyl thioether compounds with amino-end groups were synthesized by the method of arm first. Afterwards, the four different star-shaped Schiff base were prepared through the reaction activity of amino, whose basic properties and application was studied. The completed works were the several following parts:1. The synthesis of amino-end star-shaped phenyl thioether compound with benzene coreAmino-end star-shaped phenyl thioether compounds were synthesized through arm first method with benzene ring as core and phenyl thioether structure as arm. The formed compound possesses regular molecular weight and can be only dissolved in DMSO, but is good in thermostability and fluorescence. This compound can be used as fluorescent probe and also decorated by the reaction activity of amino group for further modification. Meantime, it provides referent for the synthesis of specific star-shaped amphiphilic block polymer.2. The synthesis of star-shaped phenyl thioether Schiff base formed by modifying with amino-end groupsFour star-shaped phenyl thioether Schiff base were prepared through the reaction with amino groups, which displayed different physical and chemical properties as the different functionality on the periphery. Especially, studies have shown that salicylaldehyde-Schiff base compound had excellent thermostability and solubility in many organic solvents and possessed good electrochemical properties and fluorescence properties. Due to the introduction of C=N double bonds and hydroxyl groups on ortha benzene ring, the compounds are able to coordinate with metal ions, which causes the fluorescence quenching in the solution with application in detection of trace metal ions. Star-shaped salicylicaldehyde Schiff base was also applied to the dispersion of gold nanoparticles, which were stable and within nanometer size range in narrow distribution.3. The synthesis of star-shaped amphiphilic block macromolecules with phenyl thioether as coreBased on the hydrophilicity of polyethylene glycol (PEG), amphiphilic block star macromolecular compounds were obtained by the grafting PEG to the periphery of star-shaped phenyl thioether compounds. The star, gigantic, amphiphilic block compounds displayed with good water-solubility and fluorescence, which was directly employed in protection of nanometer gold particles in the water phase.