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Synthesis and Structure of a Longitudinally Twisted Hexacene

The addition of phenyllithium to a polycyclic quinone, 9,11,12,21,22,24‐hexaphenyltetrabenzo[a,c,n,p]hexacene‐10,23‐di‐one (10), followed by SnCl2‐mediated reduction of the diol intermediate, yielded 9,10,11,12,21,22,23,24‐octaphenyltetrabenzo‐[a,c,n,p]hexacene (4). Crystallographic analysis of hexacene 4 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 4 contains within its substructure the most twisted naphthalene, anthracene, tetracene, and pentacene moieties described.

Authors:   Robert G. Clevenger, Bharat Kumar, Elizabeth M. Menuey, Kathleen Victoria Kilway
Journal:   Chemistry - A European Journal
Year:   2018
Pages:   n/a
DOI:   10.1002/chem.201705676
Publication date:   19-Jan-2018
Facts, background information, dossiers
  • pentacene
  • naphthalene
  • anthracene
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