ImageFile = Hexacene.svg
IUPACName = Hexacene
Section1 = Chembox Identifiers
CASNo = 258-31-1
PubChem = 123044
SMILES = C1=CC=C2C=C3C=C4C=C5C=C6C=CC=CC6=CC5=CC4=CC3=CC2=C1
Section2 = Chembox Properties
Formula = C26H16
MolarMass = 328.41 g/mol
Section3 = Chembox Hazards
Hexacene is an
aromaticmolecule consisting of six linearly-fused benzene rings. Hexacene and its derivatives are investigated for potential applications as organic semiconductor.
Hexacene is one of a series of linear
acenes, the previous one being pentacene(five fused benzene rings) and the next one being heptacene(seven fused benzene rings) [The CAS registry numberis CASREF|CAS=258-38-8. Molecular weight 328 g.mol-1.] .
Hexacene is very unstable, being highly reactive in the 6, 15 positions due to pi electron localization. Its spectra must be collected on freshly purified samples handled in an inert atmosphere such as nitrogen or argon. Only with very large substituents it is possible to isolate an hexacene for instance the compound "6,15-bis(tri-t-butylsilylethynyl)hexacene" which melts with decomposition at 96°C. [cite journal
author = Payne M. M., Parkin S. R., Anthony J. E.
title = Functionalized higher acenes: hexacene and heptacene
Journal of the American Chemical Society
year = 2005
volume = 127
issue = 22
pages = 8028–9
doi = 10.1021/ja051798v S0002-7863(05)01798-1 ]
The first reported synthesis of hexacene itself dates back to 1942 [cite journal
author = E. Clar
title = Eine neue Synthese des Hexacens (Aromatische Kohlenwasserstoffe, XXXIV. Mitteil.)
journal = Berichte der deutschen chemischen Gesellschaft
year = 1942
volume = 75
issue = 11
pages = 1283–1287
doi = 10.1002/cber.19420751102 ] In 1955 the compound is synthesized by
dehydrogenationof "hexacosadehydrohexacene" by palladium on carbon["Cyclic Dienes. XI. New Syntheses of Hexacene and Heptacene" William J. Bailey and Chien-Wei Liao J. Am. Chem. Soc.; 1955; 77(4) pp 992 - 993; DOI|10.1021/ja01609a055] . In 1982 hexacene is reported as a bluish green compound with decomposition at 380 degrees [cite journal
author = Angliker H., Rommel E., Wirz J.
title = Electronic spectra of hexacene in solution (ground state, triplet state, dication and dianion)
Chemical Physics Letters
year = 1982
volume = 87
issue = 2
pages = 208–12
doi = 10.1016/0009-2614(82)83589-6 ] . In 2007, a research group claimed the first reproducible unsubstituted hexacene synthesis (invalidating the previous claims) based on
photochemicaldecarbonylation of a dioneprecursor ["Revisiting the Stability of Hexacenes" Rajib Mondal, Ravi M. Adhikari, Bipin K. Shah, and Douglas C. Neckers Org. Lett.; 2007; 9(13) pp 2505 - 2508; (Letter) DOI|10.1021/ol0709376] :
The compound cannot be isolated: it dimerizes even at concentration as low as 10-4 M and reacts in solution with oxygen to the
organic peroxide. In a PMMApolymer matrix on the other hand these side-reactions are limited and the compound can survive up to 12 hours. The next homologue heptacenealso studied by this group, is even more unstable (decomposes within 4 hours).
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