Synthesis and Divergent Electronic Properties of Two Ring-Fused Derivatives of 9,10-Diphenylanthracene.
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.
Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal H3A 0B8, Quebec, Canada.
M Rajeswara
MR
Rao
Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal H3A 0B8, Quebec, Canada.
Hayden T
HT
Black
Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal H3A 0B8, Quebec, Canada.
Dmitrii F
DF
Perepichka