Preparation Of Amides Materials Based On Phenanthroimidazole And Their Fluorescence Applications

Amide, as a class of important carboxylic acid derivative, has played an extremelyimportant role in material science, target sensing, life, health and other areas. Some specialfunctions would be realized or strengthed via intramolecular hydrogen bonding, coordinationor chelating effects for the presence of the carbonyl and amino in amide bond.Phenanthro[9,10-d]imdizole, has attracted tremendous attention as a efficient blue-emittingbuilding block due to their simple synthesis, excellent thermal properties and highfluorescence quantum yields, and become a new star block in electro-photo field. This thesisfocuses on combining structure-properties advantage of amide group with opticalcharacteristics of phenanthro[9,10-d]imdizole to develop its potential in functional fluorescentfield via UV-vis, fluorescence spectra and electrochemistry data.Base on our pervious phenanthro[9,10-d]imdizole research achievement, the substitutepositions at N1and C2are chosen to extended the conjugated system. Chloride method ispreferred from various amide preparation systems, and become a main synthetic method inpaper. By simple substitution and modification in functional group, the binding mode is triedbetween phenanthro[9,10-d]imdizole and amide derivatives, and the various carboxylic acidderivatives are prepared and applied in the fluorescence field.By selecting the formyl carboxylic or amino acid as the raw material alternatively,C-COOH and N-COOH structure are prepared via "one pot" chemical reaction. Comparisonwith their UV absorption and emission spectra, substituent effects of N1and C2inphenanthro[9,10-d]imdizole are further defined;Two chloride structures are obtained by simplerefluxing in thionyl chloride, and named as C-COCl and N-COCl. They exhibit good waterstability. There are significant differences because of substitution sites change in solvent testand pH sensing experiment. And cell staining experiments prove that the two dyes may beused as potential fluorescence probe;Aniline is chosen as raw materials for amide modelcompounds, and two kinds of structure were prepared as CA and NA. The significant responsein low field region of NMR proved the existence of amide structure base onphenanthro[9,10-d]imdizole. Comparison with their fluorescence spectra, solvent effect, theelectrochemical data and the pH effect, the data prove that NA would be a potential buildingblock of better photoelectric materials; C2substituted group is optimized in NA structure from the benzene ring to naphthalene ring structure. Comparing with their fluorescence properties atalpha and beta position, combining with the Lippert-Mataga equation analysis,electrochemical data and other results, the limited conjugate linking method may be morefavorable for deep-blue emitting materials.Through optimizing the structure and optical study of N1and C2inphenanthro[9,10-d]imdizole carboxylic acid derivatives, the amide structures base onphenanthro[9,10-d]imdizole is a kind of great potential photoelectric materials in keeping withdeep blue solid state emission and adjusting excited state structure.