Synthesis and Structure of a Longitudinally Twisted Hexacene.

Abstract: The addition of phenyllithium to a polycyclic quinone, 9,11,12,21,22,24‐hexaphenyltetrabenzo[<italic>a</italic>,<italic>c</italic>,<italic>n</italic>,<italic>p</italic>]hexacene‐10,23‐dione (<bold>10</bold>), followed by SnCl2‐mediated reduction of the diol intermediate, yielded 9,10,11,12,21,22,23,24‐octaphenyltetrabenzo‐[<italic>a</italic>,<italic>c</italic>,<italic>n</italic>,<italic>p</italic>]hexacene (<bold>4</bold>). Crystallographic analysis of hexacene <bold>4</bold> showed it to possess a longitudinal twist of 184°, which was in good agreement with AM1 calculations. In addition to being the most twisted acene synthesized to this point, compound <bold>4</bold> contains within its substructure the most twisted naphthalene, anthracene, tetracene, and pentacene moieties described. [ABSTRACT FROM AUTHOR]