diethyl 2,2'-diamino-(E)-stilbene-4,4'-dicarboxylate | 150713-17-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: diethyl 2,2'-diamino-(E)-stilbene-4,4'-dicarboxylate
• 英文别名: ethyl 3-amino-4-[(E)-2-(2-amino-4-ethoxycarbonylphenyl)ethenyl]benzoate
• CAS: 150713-17-0
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: GBUHYQNZOKWRKC-AATRIKPKSA-N

物化性质

• 沸点：
  581.1±50.0 °C(predicted)
• 密度：
  1.239±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2,2'-diamino-(E)-stilbene-4,4'-dicarboxylate 在 盐酸 、 sodium azide 、 sodium nitrite 作用下， 以 邻二氯苯 为溶剂， 反应 1.5h， 生成 Diethyl 5,10-dihydroindolo<3,2-b>indole-2,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and properties of diethyl 5,10-dihetera-5,10-dihydroindeno[2,1-a]indene-2,7-dicarboxylates

  摘要：

  A series of six heterocyclic diesters lb-6b containing all combinations of nitrogen, sulfur, and selenium has been prepared from a common precursor, diethyl 2,2'-dinitrostilbene-4,4'-dicarboxylate. Electrochemical analysis showed oxidation potential increases in the order N < Se < S, and the same trend was observed for maxima of UV absorbance. Electrochemical oxidation of indoloindole lb (but not the other members of the series) generates a persistent radical cation whose properties were investigated. Diesters containing sulfur and selenium (but not nitrogen) form S(A) liquid crystals. A new synthetic method leading to the indolo[1,2-b]indazole ring system has been found.

  DOI：

  10.1021/jo00071a034
• 作为产物：
  描述：

  4-chloromethyl-3-nitrobenzoic acid 在 盐酸 、 氯化亚砜 、 硫酸 、 硝酸 、 sodium ethanolate 、 铁粉 作用下， 以 乙醇 为溶剂， 反应 9.5h， 生成 diethyl 2,2'-diamino-(E)-stilbene-4,4'-dicarboxylate
  参考文献：
  名称：

  Synthesis and properties of diethyl 5,10-dihetera-5,10-dihydroindeno[2,1-a]indene-2,7-dicarboxylates

  摘要：

  A series of six heterocyclic diesters lb-6b containing all combinations of nitrogen, sulfur, and selenium has been prepared from a common precursor, diethyl 2,2'-dinitrostilbene-4,4'-dicarboxylate. Electrochemical analysis showed oxidation potential increases in the order N < Se < S, and the same trend was observed for maxima of UV absorbance. Electrochemical oxidation of indoloindole lb (but not the other members of the series) generates a persistent radical cation whose properties were investigated. Diesters containing sulfur and selenium (but not nitrogen) form S(A) liquid crystals. A new synthetic method leading to the indolo[1,2-b]indazole ring system has been found.

  DOI：

  10.1021/jo00071a034

文献信息

• ORGANIC NANOFIBER STRUCTURE BASED ON SELF-ASSEMBLED ORGANOGEL, ORGANIC NANOFIBER TRANSISTOR USING THE SAME, AND METHOD OF MANUFACTURING THE ORGANIC NANOFIBER TRANSISTOR
  申请人：SAMSUNG ELECTRONICS CO., LTD.

  公开号：US20130069040A1

  公开（公告）日：2013-03-21

  An organic nanofiber including a gelled organic semiconductor compound. Also disclosed is an organic semiconductor transistor and a method of manufacturing an organic semiconductor transistor.

  一种有凝胶有机半导体化合物的有机纳米纤维。同时还公开了一种有机半导体晶体管以及一种制造有机半导体晶体管的方法。
• High-performance organic semiconductors for thin-film transistors based on 2,7-divinyl[1]benzothieno[3,2-b]benzothiophene
  作者：Myoung-Chul Um、Jeonghun Kwak、Jung-Pyo Hong、Jihoon Kang、Do Yeung Yoon、Seong Hoon Lee、Changhee Lee、Jong-In Hong

  DOI：10.1039/b808438f

  日期：——

  We have synthesized two novel organic semiconductors, which have a symmetrically substituted 2,7-divinyl[1]benzothieno[3,2-b]benzothiophene backbone. They show good electrical performances on a SiO2/Si substrate, with high field-effect mobilities of up to 0.4 cm2V−1 s−1, and can easily be synthesized in large quantities. In addition, there is no significant change in the mobility of DPV-BTBT even after the device is exposed to air for at least 60 days (further monitoring is in progress), showing that it is a promising air-stable p-channel organic semiconductor that can be applied to all-organic flexible electronic devices.

  我们合成了两种新型有机半导体，它们具有对称取代的 2,7- 二乙烯基[1]苯并噻吩并[3,2-b]苯并噻吩骨架。它们在二氧化硅/硅衬底上显示出良好的电性能，场效应迁移率高达 0.4 cm2V-1 s-1，而且很容易大量合成。此外，DPV-BTBT 器件在空气中暴露至少 60 天后，其迁移率也没有发生明显变化（正在进一步监测中），这表明它是一种具有良好空气稳定性的 p 沟道有机半导体，可应用于全有机柔性电子器件。
• US8362464B2
  申请人：——

  公开号：US8362464B2

  公开（公告）日：2013-01-29
• US9029840B2
  申请人：——

  公开号：US9029840B2

  公开（公告）日：2015-05-12
• Synthesis and properties of diethyl 5,10-dihetera-5,10-dihydroindeno[2,1-a]indene-2,7-dicarboxylates
  作者：Piotr Kaszynski、Dennis A. Dougherty

  DOI：10.1021/jo00071a034

  日期：1993.9

  A series of six heterocyclic diesters lb-6b containing all combinations of nitrogen, sulfur, and selenium has been prepared from a common precursor, diethyl 2,2'-dinitrostilbene-4,4'-dicarboxylate. Electrochemical analysis showed oxidation potential increases in the order N < Se < S, and the same trend was observed for maxima of UV absorbance. Electrochemical oxidation of indoloindole lb (but not the other members of the series) generates a persistent radical cation whose properties were investigated. Diesters containing sulfur and selenium (but not nitrogen) form S(A) liquid crystals. A new synthetic method leading to the indolo[1,2-b]indazole ring system has been found.