2,5-bis(4-aminophenylenesulfanyl)thiophene | 211238-27-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,5-bis(4-aminophenylenesulfanyl)thiophene
• 英文别名: 4,4 inverted exclamation mark-[Thiophene-2,5-diylbis(sulfanediyl)]dianiline；4-[5-(4-aminophenyl)sulfanylthiophen-2-yl]sulfanylaniline
• CAS: 211238-27-6
• 化学式: C₁₆H₁₄N₂S₃
• 分子量: 330.499
• InChiKey: WFDDMRRZEHUPCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-二氯噻吩 、 4-氨基苯硫酚 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以80%的产率得到2,5-bis(4-aminophenylenesulfanyl)thiophene
  参考文献：
  名称：

  Thiophene and Selenophene Donor–Acceptor Polyimides as Polymer Electrets for Nonvolatile Transistor Memory Devices

  摘要：

  We report the nonvolatile memory characteristics of n-type N,N'-bis(2-phenylethyl)perylene-3,4:9,10-tetracarboxylic diimide (BPE-PTCDI) based organic field-effect transistors (OFET) using the polyimide electrets of poly[2,5-bis(4-aminophenylenesulfanyl)selenophene-hexafluoroisopropylidenediphthalimide] (PI(APSP-6FDA)), poly[2,5-bis(4-aminophenylenesulfanyl)thiophene-hexafluoroisopropylidenediphthalimide] (PI(APST-6FDA)), and poly(4,4'-oxidianiline-4,4'-hexafluoroisopropylidenediphthalic anhydride) (PI(ODA-6FDA)). Among those polymer electrets, the OFET memory device based on PI(APSP-6FDA) with a strong electron-rich selenophene moiety exhibited the highest field-effect mobility and I-on/I-off current ratio of 10(5) due to the formation of the large grain size of the BPE-PTCDI film. Furthermore, the device with PI(APSP-6FDA) exhibited the largest memory window of 63 V because the highest HOMO energy level and largest electric filed facilitated the charges transferring from BPE-PTCDI and trapping in the PI electret. Moreover, the charge transfer from BPE-PTCDI to the PI(APSP-6FDA) or PI(APST-6FDA) electrets was more efficient than that of PI(ODA-6FDA) due to the electron-donating heterocyclic ring. The nanowire device with PI(APSP-6FDA) showed a relatively larger memory window of 82 V, compared to the thin film device. The present study suggested that the donor acceptor polyimide electrets could enhance the capabilities for transferring and store the charges and have potential applications for advanced OFET memory devices.

  DOI：

  10.1021/ma301326r

文献信息

• Thiophene and Selenophene Donor–Acceptor Polyimides as Polymer Electrets for Nonvolatile Transistor Memory Devices
  作者：Ying-Hsuan Chou、Nam-Ho You、Tadanori Kurosawa、Wen-Ya Lee、Tomoya Higashihara、Mitsuru Ueda、Wen-Chang Chen

  DOI：10.1021/ma301326r

  日期：2012.9.11

  We report the nonvolatile memory characteristics of n-type N,N'-bis(2-phenylethyl)perylene-3,4:9,10-tetracarboxylic diimide (BPE-PTCDI) based organic field-effect transistors (OFET) using the polyimide electrets of poly[2,5-bis(4-aminophenylenesulfanyl)selenophene-hexafluoroisopropylidenediphthalimide] (PI(APSP-6FDA)), poly[2,5-bis(4-aminophenylenesulfanyl)thiophene-hexafluoroisopropylidenediphthalimide] (PI(APST-6FDA)), and poly(4,4'-oxidianiline-4,4'-hexafluoroisopropylidenediphthalic anhydride) (PI(ODA-6FDA)). Among those polymer electrets, the OFET memory device based on PI(APSP-6FDA) with a strong electron-rich selenophene moiety exhibited the highest field-effect mobility and I-on/I-off current ratio of 10(5) due to the formation of the large grain size of the BPE-PTCDI film. Furthermore, the device with PI(APSP-6FDA) exhibited the largest memory window of 63 V because the highest HOMO energy level and largest electric filed facilitated the charges transferring from BPE-PTCDI and trapping in the PI electret. Moreover, the charge transfer from BPE-PTCDI to the PI(APSP-6FDA) or PI(APST-6FDA) electrets was more efficient than that of PI(ODA-6FDA) due to the electron-donating heterocyclic ring. The nanowire device with PI(APSP-6FDA) showed a relatively larger memory window of 82 V, compared to the thin film device. The present study suggested that the donor acceptor polyimide electrets could enhance the capabilities for transferring and store the charges and have potential applications for advanced OFET memory devices.