Synthesis of Conjugated Aryleneethynylenesiloles Dendron  

作　　者：Liu Jie Yan Chenxu Li Shanshan Wang Chengyun Shen Yongjia 

机构地区：[1]Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, China

出　　处：《Chinese Journal of Chemistry》2012年第12期2861-2868,共8页中国化学（英文版）

基　　金：supported by National Natural Science Foundation of China （Nos. 20872035, 21076078）, and Specialized Research Fund for the Doctoral Program of Higher Education （No. 20070251018）.

摘　　要：Three routes were designed to synthesize a n-conjugated aryleneethynylenesiloles dendron. With the desilylation of the disilole mono（silylethynyl） derivative in the presence of potassium carbonate （K2CO3）, the silole-containing oligomer has been successfully synthesized without impact on the Si-（CH3）2 group. The disilole mono- （silylethynyl） derivative was prepared by means of the Sonogashira heterocoupling reaction between the diacetylene compound and asymmetrical silole, catalyzed by the dichloro bis（triphenylphosphine）palladium, in a divergent synthesis. Due to their steric effect and triethynylbenzene self-coupling Glaser reaction, the endeavour to prepare the dendron by controlling the molar ratio of asymmetrical silole and 1,3,5-triethynylbenzene was failed. The another attempt to prepare the dendron by different desilylation condition of triisopropylsilyl group and trimethylsilyl group was also failed, the desilylation of Si-（CH3）2 group in silacyclopentadiene unit was also easily accomplished in the presence of tetrabutylammonium fluoride（Bu4NF）, whereas no reaction occurred when K2CO3 was used instead of Bu4NF.Three routes were designed to synthesize a n-conjugated aryleneethynylenesiloles dendron. With the desilylation of the disilole mono（silylethynyl） derivative in the presence of potassium carbonate （K2CO3）, the silole-containing oligomer has been successfully synthesized without impact on the Si-（CH3）2 group. The disilole mono- （silylethynyl） derivative was prepared by means of the Sonogashira heterocoupling reaction between the diacetylene compound and asymmetrical silole, catalyzed by the dichloro bis（triphenylphosphine）palladium, in a divergent synthesis. Due to their steric effect and triethynylbenzene self-coupling Glaser reaction, the endeavour to prepare the dendron by controlling the molar ratio of asymmetrical silole and 1,3,5-triethynylbenzene was failed. The another attempt to prepare the dendron by different desilylation condition of triisopropylsilyl group and trimethylsilyl group was also failed, the desilylation of Si-（CH3）2 group in silacyclopentadiene unit was also easily accomplished in the presence of tetrabutylammonium fluoride（Bu4NF）, whereas no reaction occurred when K2CO3 was used instead of Bu4NF.

关 键 词：HETEROCYCLES DENDRIMERS SILOLE sonogashira reaction DESILYLATION 

分 类 号：TQ317[化学工程—高聚物工业] O152.1[理学—数学]