Synthesis, Crystal Structure, and Optoelectronic Properties of 2,7-bis(benzo[b]thiophen-2-yl)-4,5-Diazafluoren-9-One

Abstract

2,7-Bis(benzo[b]thiophen-2-yl)-4,5-diazafluoren-9-one (BT-DAFO) is synthesized and crystallized and its optoelectronic properties are studied. The compound has the layered crystal packing formed by π-stacking interactions with a shift along the long molecular axis. The physicochemical and optoelectronic properties of BT-DAFO are investigate. It has photoluminescence quantum yields of 29% and 9% in the tetrahydrofuran solution and single crystals respectively. The crystal structure is found to have a high anisotropy of the charge transport. A series of top-gate organic field-effect transistors is manufactured based on BT-DAFO single crystals, however, the charge transport was not detected. With regard to the favorable crystal structure, diazafluorenone derivatives are promising materials for organic electronics, however, further functionalization is needed to improve the solubility and modify the carbonyl group.