Pyridone-Doped Acenes with Improved Stability

Abstract

Besides the peripheral modification, the introduction of heteroatoms to modulate the property of longer acenes with improved chemical stability has been extensively studied for their potential applications in organic electronics. However, the utilization of 4-pyridone, a common unit in the air- and photo-stable acridone and quinacridone, to decorate higher acenes with increased stability has not been realized yet. Here we present the synthesis of a series of monopyridone-doped acenes up to heptacene via the palladium-catalyzed Buchwald-Hartwig amination of aniline and dibromo-ketone. The effect of pyridone on the property of doped acenes were investigated experimentally and computationally. With the π-extension of doped acenes, the pyridone ring shows the weakened conjugation and gradual loss of aromaticity. The doped acenes demonstrate enhanced stability in solution and maintain the electronic communication between the acene planes.