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A Superior Synthesis of Longitudinally Twisted Acenes
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2017-12-07 , DOI: 10.1002/chem.201704501
Robert G. Clevenger,Bharat Kumar,Elizabeth M. Menuey,Gene-Hsiang Lee,Dustin Patterson,Kathleen V. Kilway

Seven longitudinally twisted acenes (an anthracene, two tetracenes, three pentacenes, and a hexacene) have been synthesized by the addition of aryllithium reagents to the appropriate quinone precursors, followed by SnCl2‐mediated reduction of their diol intermediates, and several of these acenes have been crystallographically characterized. The new syntheses of the three previously reported twisted acenes, decaphenylanthracene (1), 9,10,11,20,21,22‐hexaphenyltetrabenzo[a,c,l,n]pentacene (2), and 9,10,11,12,13,14,15,16‐octaphenyldibenzo[a,c]tetracene (14), resulted in a reduction of the number of synthetic steps. As a consequence their overall yields were increased by factors of 50‐, 24‐, and 66‐fold, respectively. All of the twisted acene syntheses reported here are suitable for the synthesis of at least gram quantities of these remarkable hydrocarbon materials.

中文翻译:

纵向扭曲并苯的优异合成方法

通过在适当的醌前体中添加芳基锂试剂,然后通过SnCl 2介导的二醇中间体还原反应,合成了七个纵向扭曲的并苯(蒽,两个四烯,三个并五苯和并六苯)。已经在晶体学上进行了表征。新合成的三种先前报道的双并苯,十苯并蒽(1),9,10,11,20,21,22-六苯基四苯并[ acln ]并五苯(2)和9,10,11, 12,13,14,15,16-八苯基二苯并[ ac ]并四苯(14),从而减少了合成步骤的数量。结果,它们的总产量分别增加了50倍,24倍和66倍。本文报道的所有扭曲并苯合成均适合于合成至少克量的这些引人注目的烃类材料。
更新日期:2017-12-07
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