Developing and Comparing 2,6-Anthracene Derivatives: Optical, Electrochemical, Thermal, and Their Use in Organic Thin Film Transistors.

Anthracene-based semiconductors have attracted great interest due to their molecular planarity, ambient and thermal stability, tunable frontier molecular orbitals and strong intermolecular interactions that can lead to good device field-effect transistor performance. In this study, we report the synthesis of six anthracene derivatives which were di-substituted at the 2,6-positions, their optical, electrochemical and thermal properties, and their single crystal structures. It was found that 2,6-functionalization with various fluorinated phenyl derivatives led to negligible changes in the optical behaviour while influencing the electrochemical properties. Furthermore, the choice of fluorinated phenyl moiety had noticeable effects on melting point and thermal stability (Δ < 55 °C and Δ < 65 °C). Bottom-gate top-contact (BGTC) organic thin transistors (OTFTs) were fabricated and characterized using the 2,6-anthracene derivatives as the semiconducting layer. The addition of fluorine groups on the phenyl groups led to a transition from p-type behaviour to n-type behaviour in BGBC OTFTs.