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The design and synthesis of ferrocene-functionalized organic small molecules using quinoline cores are rendered to achieve a ternary write-once-read-many (WORM) memory device. Introducing an electron-withdrawing group into the ferrocene system changes the compounds' photophysical, electrochemical, and memory behavior. The compounds were synthesized with and without an acetylene bridge between the ferrocene unit and quinoline. The electrochemical studies proved the oxidation behavior with a slightly less intense reduction peak of the ferrocene unit, demonstrating that quinolines have more reducing properties than ferrocene with bandgaps ranging from 2.67-2.75 eV. The single crystal analysis of the compounds also revealed good interactive interactions, ensuring good molecular packing. This further leads to a ternary WORM memory with oxidation of the ferrocene units and charge transfer in the compounds. The devices exhibit on/off ratios of 10 4 and very low threshold voltages of -0.58/-1.02 V with stabilities of 10 3 s and 100 cycles of all the states through retention and endurance tests., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

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.

Donor-Acceptor systems are highly appreciated in the field of organic memory devices due to their efficient charge transport within the systems. In this work, we have designed and synthesized a D-π-A system constituting ester-flanked quinolines and functionalized triarylamines (TAA) through a single-step cross-coupling reaction to fabricate memory devices via Write-Once Read-Many times (WORM) non-volatile memory. Structure-property relationships are reconnoitered for these conjugated D-π-A systems through a series of UV, fluorescence, XRD, DFT, and memory characterizations. The UV and CV data show efficient charge transfer with intramolecular charge transfer occurring at 407-417 nm and a short band gap of 2.56-2.65 eV. An enhancement in the resistive switching behavior of the memory devices is observed for the compounds with simple TAA-quinoline and tert-butylphenyl substituted TAA and fluorophenyl substituted quinoline due to balanced charge distribution in the compounds. This enhanced switching induces an on/off ratio of 10 3 by generating a highly ordered arrangement in the thin films. The HOMO, LUMO levels, and the ESP images together estimate a charge transfer and charge trapping as the plausible mechanism for the solution-processable WORM memory devices. The longer retention time (10 3  s) and lower threshold voltages (-1.21--2.12 V) of the devices makes them intriguing compounds for memory applications., (© 2022 Wiley-VCH GmbH.)