cyclohexane-1,4-dione bis(phenylhydrazone) | 29184-72-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyclohexane-1,4-dione bis(phenylhydrazone)
• 英文别名: Cyclohexan-1,4-dion-bis-phenylhydrazon；N-[[4-(phenylhydrazinylidene)cyclohexylidene]amino]aniline
• CAS: 29184-72-3
• 化学式: C₁₈H₂₀N₄
• 分子量: 292.384
• InChiKey: HHMVURQDZJPWEC-UHFFFAOYSA-N

物化性质

• 沸点：
  463.5±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  48.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclohexane-1,4-dione bis(phenylhydrazone) 在 硫酸 作用下， 反应 0.25h， 生成 吲哚并[3,2-b]咔唑
  参考文献：
  名称：

  Indolo[3,2-b]carbazole-Based Thin-Film Transistors with High Mobility and Stability

  摘要：

  Proper functionalization of indolo[3,2-b]carbazole led to a new class of high-performance organic semiconductors suitable for organic thin-film transistor (OTFT) applications. While 5,11-diaryl-substituted indolo[3,2-b]carbazoles without long alkyl side chains provided amorphous thin films upon vacuum deposition, those with sufficiently long alkyl side chains such as 5,11-bis(4-octylphenyl)indolo[3,2-b]carbazole self-organized readily into highly crystalline layered structures under similar conditions. OTFTs using channel semiconductors of this nature exhibited excellent field-effect properties, with mobility up to 0.12 cm(2) V-1 s(-1) and current on/off ratio to 10(7). As this class of organic semiconductors has relatively low HOMO levels and large band gaps, they also displayed good environmental stability even with prolonged exposure to amber light, an appealing characteristic for OTFT applications.

  DOI：

  10.1021/ja0456149
• 作为产物：
  描述：

  苯肼 、 1,4-环己二酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 cyclohexane-1,4-dione bis(phenylhydrazone)
  参考文献：
  名称：

  Indolo[3,2-b]carbazole-Based Thin-Film Transistors with High Mobility and Stability

  摘要：

  Proper functionalization of indolo[3,2-b]carbazole led to a new class of high-performance organic semiconductors suitable for organic thin-film transistor (OTFT) applications. While 5,11-diaryl-substituted indolo[3,2-b]carbazoles without long alkyl side chains provided amorphous thin films upon vacuum deposition, those with sufficiently long alkyl side chains such as 5,11-bis(4-octylphenyl)indolo[3,2-b]carbazole self-organized readily into highly crystalline layered structures under similar conditions. OTFTs using channel semiconductors of this nature exhibited excellent field-effect properties, with mobility up to 0.12 cm(2) V-1 s(-1) and current on/off ratio to 10(7). As this class of organic semiconductors has relatively low HOMO levels and large band gaps, they also displayed good environmental stability even with prolonged exposure to amber light, an appealing characteristic for OTFT applications.

  DOI：

  10.1021/ja0456149

文献信息

• Synthesis and alkylation of indolo[3,2-b]carbazoles
  作者：Larisa N Yudina、Jan Bergman

  DOI：10.1016/s0040-4020(03)00029-2

  日期：2003.2

  Double Fischer cyclisation was used to prepare indolo[3,2-b]carbazole and its 2,8-di-OMe, OH, Br and F-derivatives. N-monosubstituted derivatives of indolo[3,2-b]carbazole (methyl, hydroxymethyl, dimethylaminoethyl) were obtained starting from 5,11-di-Boc-indolo[3,2-b]carbazole.

  使用双费歇尔环化反应制备吲哚并[3,2- b ]咔唑及其2,8-二-OMe，OH，Br和F衍生物。从5，11-二-Boc-吲哚[3，2- b ]咔唑开始获得吲哚[3，2- b ]咔唑的N-单取代衍生物（甲基，羟甲基，二甲基氨基乙基）。
• Baeyer; Noyes, Chemische Berichte, 1889, vol. 22, p. 2176
  作者：Baeyer、Noyes

  DOI：——

  日期：——
• Indolo[3,2-<i>b</i>]carbazole-Based Thin-Film Transistors with High Mobility and Stability
  作者：Yiliang Wu、Yuning Li、Sandra Gardner、Beng S. Ong

  DOI：10.1021/ja0456149

  日期：2005.1.1

  Proper functionalization of indolo[3,2-b]carbazole led to a new class of high-performance organic semiconductors suitable for organic thin-film transistor (OTFT) applications. While 5,11-diaryl-substituted indolo[3,2-b]carbazoles without long alkyl side chains provided amorphous thin films upon vacuum deposition, those with sufficiently long alkyl side chains such as 5,11-bis(4-octylphenyl)indolo[3,2-b]carbazole self-organized readily into highly crystalline layered structures under similar conditions. OTFTs using channel semiconductors of this nature exhibited excellent field-effect properties, with mobility up to 0.12 cm(2) V-1 s(-1) and current on/off ratio to 10(7). As this class of organic semiconductors has relatively low HOMO levels and large band gaps, they also displayed good environmental stability even with prolonged exposure to amber light, an appealing characteristic for OTFT applications.