diethyl (2E,5E)-2,5-bis[(5-(thiophen-2-yl)thiophen-2-ylmethylene)amino]thiophene-3,4-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: diethyl (2E,5E)-2,5-bis[(5-(thiophen-2-yl)thiophen-2-ylmethylene)amino]thiophene-3,4-dicarboxylate
• 英文别名: diethyl 2,5-bis[(E)-(5-thiophen-2-ylthiophen-2-yl)methylideneamino]thiophene-3,4-dicarboxylate
• 化学式: C₂₈H₂₂N₂O₄S₅
• 分子量: 610.824
• InChiKey: NGLHWUJQWRJBBW-CMNXJCJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  219
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,2'-联二噻吩 在 三氟乙酸 、 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 生成 diethyl (2E,5E)-2,5-bis[(5-(thiophen-2-yl)thiophen-2-ylmethylene)amino]thiophene-3,4-dicarboxylate
  参考文献：
  名称：

  对称和非对称自组装共轭噻吩甲亚胺的光物理，晶体学和电化学表征

  摘要：

  提出了新颖的由噻吩单元组成的共轭偶氮甲亚胺。通过稳定的二氨基噻吩（2）与其互补的噻吩醛的简单缩合来合成高度共轭的化合物。这些有趣的含氮噻吩单元表现出可变的反应性，导致受控的醛添加。由于不同的氨基反应性，通过明智地选择溶剂和仔细控制试剂的化学计量关系，可以一锅法合成不对称和对称的共轭偶氮甲硫氨酸，其中噻吩单元的数目不同。所得的共价共轭连接具有还原性和水解抗性。热力学E对于所有合成的甲亚胺而言，异构体是唯一形成的，这已通过晶体学研究得到证实。这些也证明了偶氮甲碱键和噻吩单元是高度平面和线性的。测得的噻吩甲亚胺的荧光和磷光与当前在功能装置中使用的噻吩类似物的荧光和磷光相似，但具有三重态形成低和带隙低至1.9 eV的优势。时间分辨和稳态温度相关的光物理现象表明，噻吩甲亚胺不会通过系统间交叉而广泛地占据其三重态流形。而是，它们的激发态能量主要通过内部转换的非辐射方式消散。发现了噻吩单元的准可逆电化学自由基阳离子形成。

  DOI：

  10.1021/jo070100o

文献信息

• Conjugated Thiophenes Having Conducting Properties and Synthesis of Same
  申请人：Skene G. William

  公开号：US20070287842A1

  公开（公告）日：2007-12-13

  The present invention relates to conjugated oligomers and polymers comprising aromatic thiophene cores. The conjugated materials are obtained by simple and efficient condensation of an aryl diamine and an aryl dialdehyde or a bifunctional aryl moiety comprising both an aldehyde and an amine. Condensation of the complementary moieties at temperatures ranging from ambient to refluxing temperatures in various solvents resulted in conjugated oligomers and polymers that can subsequently be cast into thin films. Oligomerization and polymerization can be done under mild conditions with removal of the resulting water bi-product responsible for shifting the equilibrium in favour of the conjugated products. The resulting conjugated compounds can be made conducting with dopants affording electrically conducting materials of either p-type or n-type conductors depending on the dopant selected.

  本发明涉及含有芳香硫吡咯核的共轭寡聚物和聚合物。这些共轭材料是通过芳香族二胺和芳香族二醛或具有同时含有醛和胺的双官能团芳香族基团的简单而有效的缩合反应获得的。在各种溶剂中，在从常温到沸点温度的温度范围内缩合互补的官能团，得到了可以随后铸造成薄膜的共轭寡聚物和聚合物。在温和的条件下进行寡聚和聚合，去除产生的水副产物，有利于使平衡向共轭产物方向移动。所得的共轭化合物可以通过掺杂制成导电材料，根据所选择的掺杂剂，可以得到p型或n型导体的电导材料。
• CONJUGATED THIOPHENES HAVING CONDUCTING PROPERTIES AND SYNTHESIS OF SAME
  申请人：Skene William G.

  公开号：US20120004386A1

  公开（公告）日：2012-01-05

  The present invention relates to conjugated oligomers and polymers comprising aromatic thiophene cores. The conjugated materials are obtained by simple and efficient condensation of an aryl diamine and an aryl dialdehyde or a bifunctional aryl moiety comprising both an aldehyde and an amine. Condensation of the complementary moieties at temperatures ranging from ambient to refluxing temperatures in various solvents resulted in conjugated oligomers and polymers that can subsequently be cast into thin films. Oligomerization and polymerization can be done under mild conditions with removal of the resulting water bi-product responsible for shifting the equilibrium in favour of the conjugated products. The resulting conjugated compounds can be made conducting with dopants affording electrically conducting materials of either p-type or n-type conductors depending on the dopant selected.

  本发明涉及含有芳香硫杂苯核的共轭寡聚物和聚合物。这些共轭材料是通过芳香族二胺和芳香族二醛或含有醛和胺的双官能团芳香族基团的简单高效缩合反应得到的。在各种溶剂中，将互补的官能团在环境温度到沸腾温度范围内缩合，得到共轭寡聚物和聚合物，随后可以将其铸造成薄膜。在温和的条件下进行寡聚和聚合反应，通过去除生成的水分子，使平衡向共轭产物倾斜。所得的共轭化合物可以通过掺杂剂使其导电，从而获得p型或n型导体的电导材料。
• US8034895B2
  申请人：——

  公开号：US8034895B2

  公开（公告）日：2011-10-11
• [EN] CONJUGATED THIOPHENES HAVING CONDUCTING PROPERTIES AND SYNTHESIS OF SAME<br/>[FR] THIOPHENES CONJUGUES POSSEDANT DES PROPRIETES DE CONDUCTION ET SYNTHESE DE CES DERNIERS
  申请人：UNIV MONTREAL

  公开号：WO2005073265A1

  公开（公告）日：2005-08-11

  The present invention relates to conjugated oligomers and polymers comprising aromatic thiophene cores. The conjugated materials are obtained by simple and efficient condensation of an aryl diamine and an aryl dialdehyde or a bifunctional aryl moiety comprising both an aldehyde and an amine. Condensation of the complementary moieties at temperatures ranging from ambient to refiuxing temperatures in various solvents resulted in conjugated oligomers and polymers that can subsequently be cast into thin films. Oligomerization and polymerization can be done under mild conditions with removal of the resulting water bi-product responsible for shifting the equilibrium in favour of the conjugated products. The resulting conjugated compounds can be made conducting with dopants affording electrically conducting materials of either p-type or n-type conductors depending on the dopant selected.
• Photophysical, Crystallographic, and Electrochemical Characterization of Symmetric and Unsymmetric Self-Assembled Conjugated Thiopheno Azomethines
  作者：Sergio Andrés Pérez Guarìn、Marie Bourgeaux、Stéphane Dufresne、W. G. Skene

  DOI：10.1021/jo070100o

  日期：2007.3.1

  crystallographic studies. These also demonstrated that the azomethine bonds and the thiophene units are highly planar and linear. The fluorescence and phosphorescence of the thiopheno azomethines measured are similar to those of thiophene analogues currently used in functional devices, but with the advantage of low triplet formation and band-gaps as low as 1.9 eV. The time-resolved and steady-state temperature-dependent

  提出了新颖的由噻吩单元组成的共轭偶氮甲亚胺。通过稳定的二氨基噻吩（2）与其互补的噻吩醛的简单缩合来合成高度共轭的化合物。这些有趣的含氮噻吩单元表现出可变的反应性，导致受控的醛添加。由于不同的氨基反应性，通过明智地选择溶剂和仔细控制试剂的化学计量关系，可以一锅法合成不对称和对称的共轭偶氮甲硫氨酸，其中噻吩单元的数目不同。所得的共价共轭连接具有还原性和水解抗性。热力学E对于所有合成的甲亚胺而言，异构体是唯一形成的，这已通过晶体学研究得到证实。这些也证明了偶氮甲碱键和噻吩单元是高度平面和线性的。测得的噻吩甲亚胺的荧光和磷光与当前在功能装置中使用的噻吩类似物的荧光和磷光相似，但具有三重态形成低和带隙低至1.9 eV的优势。时间分辨和稳态温度相关的光物理现象表明，噻吩甲亚胺不会通过系统间交叉而广泛地占据其三重态流形。而是，它们的激发态能量主要通过内部转换的非辐射方式消散。发现了噻吩单元的准可逆电化学自由基阳离子形成。