Studies On Carbon-carbon Coupling Reaction In Ionic Liquids And Application In The Synthesis Of Some Photoelectric Functional Compounds

Room-Temperature Ionic Liquids (RTILs) are salt-type structure compounds that are liquids between -30 and 50C. Although such salts have been known for almost a century, they have recently gained popularity as "green" alternatives to conventional solvents and attracted much attention in fundamental research and industry application because of their special properties, such as nonvolatile, nonflammable, nontoxic, recyclable, extremely high boiling , thermally and chemically stable, especially, their excellent solubility for some inorganic, organic and organometallic compounds. So they can act as promising reaction media and catalyst for synthetic organic chemistry, for example, Friedel-Crafts reactions, alkylation, hydrogenations, Diels-Alder reactions, Witting reactions, Heck reactions, Michael additions, etc.Based on the analysis and summary of related literature, two kinds of ionic liquids have been designed and synthesized. The first one is based on N-alkylpyridinium cations and variable anions. The other consists of dialkylimidazolium cations and tetrafluoroborate anions. In order to synthesize some photoelectric materials, the reaction conditions of two kinds of carbon-carbon coupling reaction, Baylis-Hillman reaction and Heck reaction, in N-alkylpyridinium and dialkylimidazolium ionic liquids have been investigated and the optimum reaction conditions were examined: To Baylis-Hillman reaction, benylpyridinium tetrafluoroborate ([C7H7Py]BF4) is found to be the most practical ionic liquid. It can not only give high yield, but also be recyclable and reusable without much drop of the yield. To Heck reaction, Pd(PPh})2d2 was found to be an efficient catalyst, and [BMIMJBF4 was a useful reaction media. Based on these study, some photoluminescence(PL) compounds have been designed and synthesized. The compounds contain fluorine or anthracene moiety which exhibit high PL efficiency and carbazole moiety which has excellent hole-transporting function. The photoluminescence properties of these compounds have been preliminary characterized.