The Synthesis Of Aromatic Vinyl Compounds And Their Application In Luminescent Probes

Due to luminescent probes technology has advantage of no radioactive contamination, analyte easily modify tag, good stability, low background signals, operate quickly and simple etal, it can be used in ion, environmental pollutants, drugs, the determination of nucleic acids, proteins and other substances, therefore luminescent probes were widely used in analytical chemistry, life sciences, medicine and other field. Aromatic vinyl compound is aryl connecting with another group by double bond, which has a important status in photoelectric materials, medicine and sensor thanks to its large conjugated system, good optical properties and small molecular weight easy to penetrate the cell membrane. In order to prepare a new type of optical probe with high sensitivity and high selectivity, a series of aromatic vinyl type optical probes which as quinoline, coumarin, naphthyridine or 1,10-phenanthroline for its optical response groups have been designed and synthesized in this paper, and we sudied the recognition performance to metal ion and anion of probes. The concrete research content includes the following several parts:1. Using aryl methyl compounds and aldehydes as raw materials, through Knoevenagel condensation reaction we designed and synthesized five aromatic vinyl type compounds luminescent probes: naphthyridine-salicylic aldehydeand compound(probe 1), quinoline-azo compound(probe 2), quinoline-coumarin(probe 3), 1,10-phenanthroline –pyridine acid(probe 4) and quinoline-benzothiazole(probe 5), the structure of final products were characterized by IR, 13 C NMR, 1H NMR and MS.2. The recognition properties to metal ions and anoins of probe 1~ 4 were investigated by absorption spectra and fluorescence spectra. Probes 1 can be used as a selective chemosensor for Hg2+, Ag+ and F-, and probe 2 can choose identify Ac- and Cu2+ with the ratio of absorption. probe 3 can choose identify Ac- in proton solution-ethanol. Howevere probe 4 has fluorescence quenching recognition for Hg2+ and Ag+ in aqueous solution. In addition, the metal or anoin complexation sites, stoichiometric ratio and mechanism were confirmed by titration spectra, Infrared spectrum, 1H NMR and ITC experiments.