Tailoring the Resistive Switching WORM Memory Behavior of Functionalized Bis(triphenylamine)

To better understand the structure–property relationship and the significance of the donor–acceptor (D–A) system in resistive memory devices, a series of new organic small molecules with A-π-D-π-A- and D-π-D-π-D-based architecture comprising a bis(triphenylamine) core unit and ethynyl-linked electron donor/acceptor arms were designed and synthesized. The devices with A-π-D-π-A structures exhibited write-once-read-many memory behavior with a good retention time of 1000 s while those based on D-π-D-π-D molecules presented only conductor property. The compound with nitrophenyl substitution resulted in a higher ON/OFF current ratio of 10 4, and the fluorophenyl substitution exhibited the lowest threshold voltage of −1.19 V. Solubility of the compounds in common organic solvents suggests that they are promising candidates for economic solution-processable techniques. Density functional theory calculations were used to envision the frontier molecular orbitals and to support the proposed resistive switching mechanisms. It is inferred that the presence of donor/acceptor substituents has a significant impact on the highest occupied molecular orbital–lowest unoccupied molecular orbital energy levels of the molecules, which affects their memory-switching behavior and thus suggests that a D–A architecture is ideal for memory device resistance switching characteristics.