1,6- and 2,7-<i>trans</i>-β-Styryl Substituted Pyrenes Exhibiting Both Emissive and Semiconducting Properties in the Solid State

Molecular materials that are both emissive and semiconducting are highly demanding for organic optoelectronics. In this article, we report the synthesis, emissive, and semiconducting properties of 1,6 and 2,7-<i>trans</i>-β-styryl substituted pyrenes (<b>16PyE</b> and <b>27PyE</b>). The results reveal that both <b>16PyE</b> and <b>27PyE</b> are emissive and semiconducting in the solid state. The fluorescence quantum yields of crystalline solids of <b>16PyE</b> and <b>27PyE</b> were determined to be 28.8% and 27.4%, respectively. Microrods of <b>16PyE</b> and microplates of <b>27PyE</b> were found to exhibit promising optical waveguilding behavior. Furthermore, on the basis of the transfer and output curves of the respective organic field effect transistors (OFETs), thin films of <b>16PyE</b> and <b>27PyE</b> were found to show <i>p</i>-type semiconducting properties with hole mobility up to 1.66 cm²V^–1s^–1. Such dual functions (emissive and semiconducting) of <b>16PyE</b> and <b>27PyE</b> can be ascribed to the unique intermolecular interactions and packing within crystals of <b>16PyE</b> and <b>27PyE</b>. Both 1,6 and 2,7-<i>trans</i>-β-styryl substituted pyrenes show relatively strong emissions in the solid state, and their microcrystalline samples exhibit promising optical waveguilding behavior. Moreover, their thin films exhibit <i>p</i>-type semiconducting property with hole mobilities up to 1.66 cm²V^–1s^–1