Study On The Synthesis And Applications Of Triarylimidazole Derivatives

Triarylimidazole derivatives have been widely used in biomedicine, optical materials and fluorescent probe due to their biological activities, self-assembly properties and excellent optical properties. Among those reported one dimensional (1D) organic micro/nanomaterials, ultralong organic micro/nanomaterials have been demonstrated to possess interesting optical and electronic properties. However, there are no literature reports describing the synthesis of ultralong microbelts based on triarylimidazole derivative with length in the range of millimeter scale, although ultralong belts have potential application prospect in the construction of integrated microelectronic devices. In this work, ultralong microbelts of SDB were prepared by self-assembly method. The electrical properties of microbelts were also investigated. In addition, fluorescent probes have the advantages of high sensitivity and good selectivity. Triarylimidazole group can act as fluorophore owing to its excellent spectroscope properties, such as large molar extinction coefficient, high fluorescent quantum yield. A novel fluorescent probe based on triarylimidazole derivative was synthesized and used to detect mercury ion.In this paper, the main research as follows:(1) Synthesis of two kinds of triarylimidazole derivatives. Two novel compounds, named sodium4-(4,5-diphenyl-1H-imidazole-2-yl)benzoate (SDB) and l-(4-(4,5-di-phenyl-lH-imidazol-2-y])benzoyl)-4-(4-nitrophenyl)thiosemicarbazide (DIBT), have been successfully synthesized using4-(4,5-diphenyl-1H-imidazol-2-yl)benzoic acid as starting material. These compounds have been fully characterized by1H NMR and MALDI-TOF MS.(2) Self-assembly of SDB into ultralong microbelts. A self-assembly technique is developed to fabricate ultralong microbelts of SDB. The as-prepared SDB microbelts are identified to have a belt-like structure with a rectangular cross section. All the obtained microbelts under optimal conditions have a relatively uniform size of about5.0μm in width,2.0μin thickness and approximately5.0mm in length. Particularly, the length of the SDB microbelts can be readily controlled by adjusting the SDB concentration as well as the aging temperature. In addition, the electrical and optical properties of the as-prepared microbelts are also investigated. These results should be significant in triarylimidazole derivatives crystallization and their potential application in optoelectronic devices.(3) Fluorescent mercury chemodosimeter based on triphenylimidazole derivative. A highly selective chemodosimeter, DIBT, for Hg2+detection was fabricated using triphenylimidazole group as the fluorescent signal unit and thiosemicarbazide group as the reaction unit. Upon the addition of Hg2+, the probe displayed a red-shifted fluorescence spectrum and as well as a increased fluorescence intensity due to the irreversible Hg2+-promoted1,3,4-oxadiazole formation through the desulfuriazation reaction of thiosemicarbazide. With the aid of the fluorescence spectrometer, the chemodosimeter exhibited a detection limit of3.0×10-8(S/N=3) with a linear range from1.5×10-6M to5×10-6M. Interferences from other common cations associated with Hg2+analysis were effectively inhibited.