Synthesis And Fluorescence Properties Of M-diarylaniline And Their Derivatives

The dissertation consists of synthesis and fluorescence properties of m-diarylaniline and their derivatives; palladium catalyzed cross-coupling reaction of m-terphenylamine and aryl bromides in the synthesis of diarylaniline with aryl bromide.A series of m-diarylaniline compounds are synthesized and characterized. Due to their superior conjugation system and intensive fluorescence properties, they could be used as precursors for small molecule luminescent materials with good prospect in OLEDs.5,7-diphenylquinoline is therefore synthesized from m-terphenylamine, further reaction with phenyl lithium prepared in situ led to the formation of 2,5,7-diphenylquinoline. During the synthetic procedure, modification was done for classical Skraup reaction to give rise a better result.Cu（I）-aminoacid system is found to be inactive for Buchwald-Hartwig coupling reaction between m-terphenylamine and aryl bromide. When Pd-phosphine system is used to catalyze diarylaniline with aryl bromide, better results are found. Cross-coupling reaction of m-terphenylamine and aryl bromides catalyzed by various palladium catalytic systems are studied in detail. Besides catalyst themselves, the structure of substrates are also found to have strong influence on results. Comparison of different catalytic systems proves that of Pd₂（dba）₃ and P（t-Bu）₃ generally displays the best catalytic activitiy for this kind of coupling reaction.Both m-diarylaniline and their derivatives display good fluorescence properties.