Diaceno[a,e]pentalenes: An Excellent Molecular Platform for High-Performance Organic Semiconductors.

Three diaceno[a,e]pentalene analogues with pendant sterically bulky di-tert-butylphenyl groups have been designed and synthesized. With the extension of the conjugated molecular framework, the molecular arrangement is apparently tuned by the balance between the π-extended surface and pendant alkyl or aryl substituents. Theoretical calculations of the morphologies were in good agreement with the experimental results. Ambient-stable field-effect transistors based on dianthraceno[a,e]pentalene (DAP) have been fabricated, which exhibited excellent hole mobilities (up to 6.55 cm(2) V(-1) s(-1)). Thus, this study has shown that diaceno[a,e]pentalenes are stable even with an extraordinarily large π-surface area, and may thus serve as excellent molecular platforms for further exploring high-performance semiconducting materials.