ol5b02009_si_003.cif (1.61 MB)

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

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posted on 04.09.2015, 00:00 by M. Rajeswara Rao, Hayden T. Black, Dmitrii F. Perepichka
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.