含噻吩基团的圆盘型多环芳烃的合成

Synthesis of Polycyclic Aromatic Hydrocarbons Containing Thiophene Groups

3-(2-噻吩)丙酸与乙醇进行酯化反应制得化合物2; 2与N-溴代琥珀酰亚胺发生取代反应制得化合物3;以间溴碘苯为原料,经Sonogashira偶联反应制得化合物5; 5与双频哪醇合二硼反应得到化合物6; 3与6经Suzuki偶联反应制得化合物7,产率63%;以八羰基二钴为催化剂,7经三聚反应制得氧化前驱体8;以三氯化铁为催化剂,8经氧化关环反应合成含噻吩基团的圆盘型多环芳烃,其结构经UV-Vis和MALDI-TOF-MS确证。

Compound 3 was obtained by the reaction of esterification of3-(2-thiophene)propionic acid with ethanol,and then reaction with1-bromo-2,5-pyrrolidinedione.Coupound3was coupled with m-bromoiodobenzene by Sonogashira coupling reaction to afford coupound 5,which was further treated with bis(pinacolato)diboron to give coupound 6.Coupound3and6were coupled through Suzuki coupling reaction to achive coupound7with yield of63%.Coupound 7 was then polymerizated in the presence of catalytic amound of dicobaltoctacarbonyl to provide coupound8,which was cyclization in the presence of ferric chloride to give polycyclic aromatic hydrocarbons containing thiophene groups.The structure was confirmed by UV-Vis and MALDI-TOF-MS.