Vorona Mikhail Y, Yutronkie Nathan J, Melville Owen A, Daszczynski Andrew J, Ovens Jeffrey S, Brusso Jaclyn L, Lessard Benoît H
Department of Chemical and Biological Engineering, University of Ottawa, 161 Louis Pasteur, Ottawa, ON K1N 6N5, Canada.
Department of Chemistry and Biomolecular Sciences, University of Ottawa, 150 Louis Pasteur, Ottawa, ON K1N 6N5, Canada.
Materials (Basel). 2020 Apr 22;13(8):1961. doi: 10.3390/ma13081961.
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.
基于蒽的半导体因其分子平面性、环境和热稳定性、可调节的前沿分子轨道以及能导致良好器件场效应晶体管性能的强分子间相互作用而备受关注。在本研究中，我们报告了六种在2,6位双取代的蒽衍生物的合成、它们的光学、电化学和热性质以及它们的单晶结构。研究发现，用各种氟化苯基衍生物进行2,6-官能化对光学行为的影响可忽略不计，同时会影响电化学性质。此外，氟化苯基部分的选择对熔点和热稳定性有显著影响（Δ<55°C和Δ<65°C）。使用2,6-蒽衍生物作为半导体层制备并表征了底栅顶接触（BGTC）有机薄膜晶体管（OTFT）。在BGBC OTFT中，苯基上氟基团的添加导致了从p型行为到n型行为的转变。
