Study On The Synthesis And Catalytic Property Of Phenanthro[9,10-d]Imidazole Derivatives

The phenanthro[9,10-d]imidazole derivatives are a kind of nitrogen-containing heterocyclic conjugated compound,which are easy to modify and synthesize.Numerous optical,electrochemical and thermal research activities have been focused on phenanthro[9,10-d]imidazol derivatives due to their high thermal stability,excellent electron transport capability and good electroluminescence performance in electroluminescent materials and fluorescent probes.However,using phenanthro[9,10-d]imidazole derivatives as catalysts source is very rare.In our works,we have designed and synthesized two types of phenanthro[9,10-d]imidazole derivatives catalysts to overcome these deficiencies,such as the expensive,difficult to recycle and polluting the environment of traditional catalysts.Finally,their catalytic activities in the reaction of addition of diaryl phosphine oxides to alkynes,Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions were investigated.The main research contents of this thesis are as follows:The first part is the review of papers:?1?Research progress of metal complexes and organic dyes in photocatalytic reactions;?2?The progress of the synthesis of phosphine-free Pd-catalysts for the C-C coupling reactions.In the second part,two novel types of phenanthrene[9,10-d]imidazole catalysts were synthesized,and the catalytic performance were investigated.1.A series of novel phenanthrol[9,10-d]imidazole derivatives were synthesized by Debus-Radziszewski reaction.The catalytic performance in the reaction of addition of diaryl phosphine oxides to alkynes under water as solvent was studied.Meanwhile,we investigated the effect of different substituents on the catalytic activity of photocatalysts.The results showed that phenanthro[9,10-d]imidazole derivative substituted by triphenylamine group exhibited high-performance catalytic activity to synthesize Z-alkenylphosphine oxides.Mild reaction conditions and good substrate universality make these photocatalyst of great potential application value in organic photocatalytic reactions.In a word,this study expands the application of phenanthrol[9,10-d]imidazole derivatives in organic photocatalytic reactions.2.Based on the first part of the experiment,phenanthro[9,10-d]imidazole derivative was prepared,which was coordinated with palladium acetate to obtain a palladium???solid catalyst,which was characterized by HR-MS,FT-IR,XPS,EDS,TGA,SEM,TEM and ICP.The Pd-catalyst exhibited high catalytic activity in Suzuki and Heck coupling reactions in an environmentally benign water medium.Meanwhile,Sodium dodecyl sulfonate?SDS?as a phase transfer additive.Further,the Pd-catalyst?Z4?can be reused for 15 times with little decrease of activity through simple and efficient recovery.These results proved that the Pd-catalyst has a stable structure and can be recycled many times,making these photocatalyst has great potential application value in organic catalytic reaction.It is expected to be widely used in other organic catalytic reactions.The structures of all the products were confirmed by ¹H NMR,¹³C NMR,and HR-MS.Individual compound structures were confirmed by ¹⁹F NMR,³¹P NMR.