A Superior Synthesis of Longitudinally Twisted Acenes

作者：Clevenger Robert G.; Kumar Bharat; Menuey Elizabeth M.; Lee Gene-Hsiang; Patterson Dustin; Kilway Kathleen V.^*

来源：Chemistry - A European Journal, 2018, 24(1): 243-250.

DOI：10.1002/chem.201704501

• acenes
• pentacene
• quinones
• reduction
• tetracene

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.

• 出版日期2018-1-2