The Strategy for the Construction of Thiophene-based Helicene

【作者】 王华；

【Author】 Hua Wang;Engineering Research Center for Nanomaterials,Henan University;

【机构】 河南大学；

【摘要】 In organic and bioorganic chemistry,the helical framework is one of most amazing molecular structures.The construction of helical structures always shows high challenge in organic synthesis.Based on our previous work during past more than 10 years,we provide here the strategy for the construction of thiophene-based helicene.Dithienothiophene(DTT) has six isomers,which can be employed as building blocks for the construction of helicenes.There are two strategies for this issue,chemical synthesis and photochemical synthesis.In the case of chemical synthesis,the symmetric [7]helicene is normally prepared by cyclization of the DTT dimmer,and the unsymmetric [7]helicene is generated by cyclization of the di-DTT,containing two DTT isomers.In addition,silicon spiro carbon-sulfur double helicene-like compounds 2 and 3 were synthesized from DTT.The photochemical synthesis is an effective method for construction of helicenes,including monohelicene,double helicene and triple helicene.Based on dithienothiophene(DTT) as building blocks,naphthalene-cored double helicenes,including racemate(rac-1) and mesomer(meso-1) are synthesized,respectively.Further more,the triple helicenes based on DTT and diseleno[3,2-b:2’,3’-d] selenophene(DSS) have been carried out in our research group recently.更多还原

【Abstract】 In organic and bioorganic chemistry,the helical framework is one of most amazing molecular structures.The construction of helical structures always shows high challenge in organic synthesis.Based on our previous work during past more than 10 years,we provide here the strategy for the construction of thiophene-based helicene.Dithienothiophene(DTT) has six isomers,which can be employed as building blocks for the construction of helicenes.There are two strategies for this issue,chemical synthesis and photochemical synthesis.In the case of chemical synthesis,the symmetric [7]helicene is normally prepared by cyclization of the DTT dimmer,and the unsymmetric [7]helicene is generated by cyclization of the di-DTT,containing two DTT isomers.In addition,silicon spiro carbon-sulfur double helicene-like compounds 2 and 3 were synthesized from DTT.The photochemical synthesis is an effective method for construction of helicenes,including monohelicene,double helicene and triple helicene.Based on dithienothiophene(DTT) as building blocks,naphthalene-cored double helicenes,including racemate(rac-1) and mesomer(meso-1) are synthesized,respectively.Further more,the triple helicenes based on DTT and diseleno[3,2-b:2’,3’-d] selenophene(DSS) have been carried out in our research group recently.更多还原