As an important component of highly functional macromolecule semiconductor, two kinds of new diamine monomers, bis(5‐amino‐6‐methoxy‐[1,1’‐biphenyl]‐3‐yl) methanone (BAMBPM) and bis(5‐amino‐4’‐(9H‐carbazol‐9‐yl)‐6‐methoxy‐[1,1’‐biphenyl]‐3‐yl) methanone (BACzMBPM) were used as raw materials. Two kinds of soluble aromatic polyimides were prepared from BAMBPM and BACzMBPM by polycondensation with 2,2’,3,3’‐biphenyl tetracarboxylic dianhydride (BPDA) via a two‐step procedure. The obtained polyimides were sufficiently characterized, and showed superior organic solubility and excellent thermal stability, with a weight loss of 5 % weight loss above 300 °C. Memory devices with Al/polyimide/ITO structure were prepared by the traditional method of solution spin coating. Both devices show tristable characteristics, with high ON/OFF current ratios as high as 104 and long maintenance times of 104 seconds in the environmental atmosphere.
Two aggregation-induced emission (AIE) macrocycles (DMP[5]-TPE and PCP[5]-TPE) were prepared by embedding Tetraphenylethene (TPE) unit into the skeletons of Dimethoxypillar[5]arene (DMP[5]) and [15]Paracyclophane ([15]PCP) at meso position, respectively. In crystal, the PCP[5]-TPE showed a distorted cavity, and the incubation of hexane inside the DMP[5]-TPE cavity caused a distinct change in the molecular conformation compared to PCP[5]-TPE. There was no complexation between PCP[5]-TPE and 1,4-dicyanobutane (DCB). UV absorption experiments showed the distorted cavity of DMP[5]-TPE hindered association with DCB.
Three novel polyimides (PI(TPF-Br BPDA), PI(TPF-Ph BPDA), and PI(TPF-Ph-OMe BPDA)) with tetraphenyl fluorene (TPF) were synthesized and tested. The laboratorial results showed that the constructed electronic devices exhibited different memory behaviors due to the different steric hindrance substituents (bromine atom, phenyl, and 3,5-dimethoxyphenyl) in 2,7-position of TPF molecule. The memorizers based on PI(TPF-Br BPDA) and PI(TPF-Ph BPDA) presented volatile dynamic random access memory (DRAM) feature with turn-on voltages of −2.39 and +1.45 V, as same as −1.71 and +1.74 V, separately. However, the PI(TPF-Ph-OMe BPDA) based apparatus exhibited non-volatile write-once read-many-times memory (WORM) behavior with turn-on voltage of −1.13 V, due to the more charge traps of 3,5-dimethoxyphenyl moieties and higher dipole moment. The switching mechanism was verified by quantum simulation of energy level, electrostatic potential (ESP) surface and dipole moment. These results indicated that the electrical memory performance of the synthesized TPF-based PIs could be adjusted by modifying the electron donor structure.
Two asymmetric diamines [1,1′-biphenyl]-4-yl(3,5-diaminophenyl) methanone (BPDAM) and (3,5-diaminophenyl)(4′-(naphthalen-1-yl)-[1,1′-biphenyl]-4-yl) methanone(DANPBPM) were synthesized by Suzuki coupling reaction from (4-bromophenyl)(3,5-diaminophenyl) methanone (BDAM) and corresponding arylboronic acid. A series of polyimides exhibiting organic solubility were prepared from 2,2′,3,3′-biphenyl tetracarboxylic dianhydride(BPDA) and these above three new diamines via a two-stage process. The obtained polymers showed outstanding organic solubility and high thermal stability. And studies have shown that the storage device with a sandwich type configuration of Al/polyimide/ITO was prepared by the traditional liquid spin coating technology, which showed the storage capacity of flash memory type. All the polyimide-based devices showed bistable conductivity switching and nonvolatile memory behavior that had long preservation period and high ON/OFF electric current, the rate of which was 104.
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