Synthesis And Properties Of Perylene-3,4-dicarboxylic Diesters And Several Electron Donor-acceptor Molecules Based On Perylene

Due to exceptional chemmical,photo,themal and weather stability,perylene derivatives have been applied to many fields such as organic optoelectronic materials,nano materials,artificial ion receptors,fluorescent molecular probe.With high fluorescence quantum yield,perylene derivatives are kinds of fluorophore with excellent performance.Perylene-3,4,9,10-tetracarboxylic tetraesters show strong absorption from visible light region to ultraviolet region and display good solubility in organic solvents.The researches about perylene-3,4,9,10-tetracarboxylic tetraesters become more and more.However,there are little researches involving perylene-3,4-dicarboxylic diesters.Perylene-3,4-dicarboxylic diesters have higher solubility in common organic solvents,better reactivity and more reaction sites.The electron cloud density of perylene can be changed by nitration and reactivity of carbon atoms are further changed,then we can get rich varieties of substitution products.With nitro as the bridge,Other groups can be attached to perylene.The species of perylene-3,4-dicarboxylic diester derivatives are enriched and the foundations have been laid for delve into applications.In this thesis,perylene-3,4-dicarboxylic diesters are synthesized and the compounds and photophysical properties are full characterized.At the same time,based on the oxy-heterocyclic reaction,a series of novel perylenes are synthesized which take the electron-receiving group called perylenes and take the electron-donor group called 3,4-Dithia-7H-cyclopenta[a]pentalene.With keep the flatness of perylene,the foundation of further derivatization is laid.(1)In the second chapter,based on the nitration,a series of perylene-3,4-dicarboxylic diesters have been synthesized,which contains mono-,di-and tri-nitrated products.The monositration products are 1-nitro-and 9-nitro-perylene-3,4-dicarboxylic diester.The di-nitrated products are 1,6-dinitro-and 1,9-dinitro-perylene-3,4-dicarboxylic diester.The tri-nitrated product is 1,6,9-trinitro-perylene-3,4-dicarboxylic diester.The reaction of part of the nitration perylene-3,4-dicarboxylic diester and 4-tert-butyphenol is studyed deeply.The compounds and photophysical properties of above products are full characterized.(2)In the third chapter,based on oxy-heterocyclic reactions of nitro-perylene-3,4-dicarboxylic diesters at the bay position,three novel perylene derivatives have been synthesized which take the electron-receiving group called perylenes and take the electron-donor group called 3,4-dithia-7H-cyclopenta[a]pentalene.Perylene-3,4,9,10-tetracarboxylic tetraesters and perylene diimides react with fuming nitric acid.And then the nitro-perylene-3,4,9,10-tetracarboxylic tetraesters and perylene diimides react with nitro-or bromo-3,4-dithia-7H-cyclopenta[a]pentalene,getting electron donor-acceptor molecule.The compounds and photophysical properties of above products are full characterized.