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‐dione (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 hexac...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-03, Vol.24 (13), p.3113-3116
Main Authors: Clevenger, Robert G., Kumar, Bharat, Menuey, Elizabeth M., Kilway, Kathleen V.
Format: Article
Language:English
Subjects:
Anthracene
Chemistry
Crystallography
hexacene
longitudinally twisted acene
Naphthalene
polycyclic quinone
Quinones
reduction
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Summary:The addition of phenyllithium to a polycyclic quinone, 9,11,12,21,22,24‐hexaphenyltetrabenzo[a,c,n,p]hexacene‐10,23‐dione (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. Come on, let's twistacenes! The addition of phenyllithium to the appropriate polycyclic quinone precursor, followed by SnCl2‐mediated reduction of the diol intermediate, yielded 9,10,11,12,21,22,23,24‐octaphenyltetrabenzo[a,c,n,p]hexacene. X‐ray analysis of the hexacene showed it to possess an end‐to‐end torsional angle of 184°, the largest longitudinal twist to be recorded.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201705676