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Org Lett. 2015 Sep 4;17(17):4224-7. doi: 10.1021/acs.orglett.5b02009. Epub 2015 Aug 18.

Synthesis and Divergent Electronic Properties of Two Ring-Fused Derivatives of 9,10-Diphenylanthracene.

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Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal H3A 0B8, Quebec, Canada.


Two new contorted polycyclic aromatic hydrocarbons (PAHs) 1 and 2 were synthesized by acid-catalyzed benzannulation of a substituted anthracene. The isomers reveal dissimilar photophysical and redox properties with 2 having a much smaller HOMO-LUMO gap than 1. In the solid state, 2 packs in a unique two-dimensional herringbone motif that gives rise to efficient ambipolar charge transport in OFET devices, a feature not previously observed in contorted PAHs. On the other hand, 1 packs in one-dimensional dimerized π-stacks and displays insulating properties.

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