2-[(5-diethylaminothiophen-2-ylmethylene)amino]thiophene-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[(5-diethylaminothiophen-2-ylmethylene)amino]thiophene-3-carbonitrile
• 英文别名: 2-[(E)-[5-(diethylamino)thiophen-2-yl]methylideneamino]thiophene-3-carbonitrile
• 化学式: C₁₄H₁₅N₃S₂
• 分子量: 289.425
• InChiKey: BPEWRVIYKCJVOV-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 在 三氟乙酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 147.0h， 生成 2-[(5-diethylaminothiophen-2-ylmethylene)amino]thiophene-3-carbonitrile
  参考文献：
  名称：

  Tunable spectroscopic and electrochemical properties of conjugated push–push, push–pull and pull–pull thiopheno azomethines

  摘要：

  我们研究了仅由噻吩单元组成的新型偶氮甲烷。这些高度共轭的化合物是通过将空气稳定的氨基噻吩与 2-噻吩醛缩合而制备的，后者被各种电子基团取代。所制备的偶氮甲烷具有高度共轭性，并具有抗还原性和抗水解性。在 5-噻吩醛的 2 位上放置了各种电子供体和受体，从而产生了电子分散的推推、拉拉和推拉偶氮甲烷。这些电子基团会影响 HOMO 和 LUMO 水平，从而影响吸收和发射光谱。这些含氮共轭化合物的颜色横跨从黄色到蓝色的整个可见光谱。单重激发态的激发态失活主要是通过内部转换实现的，只有少量能量是通过系统间转换到三重态和荧光而耗散的。噻吩偶氮甲烷随之产生的荧光和磷光与目前用于功能器件的噻吩类似物相似，但其优点是三重态较低，HOMOâLUMO 能级可调，从 3.0 到 1.9 eV。这种化合物可以形成准可逆的电化学自由基阳离子，而氧化电位则取决于噻吩所附电子基团的性质。电子推挽系统的晶体学数据显示，偶氮甲基键是平面和线性的，它们采用 E 异构体。

  DOI：

  10.1039/b616379c

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.
• Tunable spectroscopic and electrochemical properties of conjugated push–push, push–pull and pull–pull thiopheno azomethines
  作者：Stéphane Dufresne、Marie Bourgeaux、W. G. Skene

  DOI：10.1039/b616379c

  日期：——

  Novel azomethines consisting uniquely of thiophene units were examined. The highly conjugated compounds were prepared by condensing air stable aminothiophenes with 2-thiophene aldehydes, which were substituted with various electronic groups. The resulting azomethines are highly conjugated and are both reductively and hydrolytically resistant. Various electron donating and accepting groups placed in the 2-position of 5-thiophene carboxaldehyde lead to electronically delocalized push–push, pull–pull, and push–pullazomethines. These electronic groups affect both the HOMO and the LUMO levels, which influence the absorption and emission spectra. Colors spanning the entire visible spectrum ranging from yellow to blue are possible with these nitrogen containing conjugated compounds. Excited state deactivation of the singlet excited state occurs predominately by internal conversion while only a small amount of energy is dissipated by intersystem crossing to the triplet state and by fluorescence. The ensuing fluorescence and phosphorescence of the thiopheno azomethines are similar to those of their thiophene analogues currently used in functional devices, but with the advantage of a low triplet state and tunable HOMO–LUMO energy levels extending from 3.0 to 1.9 eV. Quasi-reversible electrochemical radical cation formation is possible while the oxidation potential is dependent on the nature of the electronic group appended to the thiophene. The crystallographic data of the electronic push–push system show the azomethine bonds are planar and linear and they adopt the E isomer.

  我们研究了仅由噻吩单元组成的新型偶氮甲烷。这些高度共轭的化合物是通过将空气稳定的氨基噻吩与 2-噻吩醛缩合而制备的，后者被各种电子基团取代。所制备的偶氮甲烷具有高度共轭性，并具有抗还原性和抗水解性。在 5-噻吩醛的 2 位上放置了各种电子供体和受体，从而产生了电子分散的推推、拉拉和推拉偶氮甲烷。这些电子基团会影响 HOMO 和 LUMO 水平，从而影响吸收和发射光谱。这些含氮共轭化合物的颜色横跨从黄色到蓝色的整个可见光谱。单重激发态的激发态失活主要是通过内部转换实现的，只有少量能量是通过系统间转换到三重态和荧光而耗散的。噻吩偶氮甲烷随之产生的荧光和磷光与目前用于功能器件的噻吩类似物相似，但其优点是三重态较低，HOMOâLUMO 能级可调，从 3.0 到 1.9 eV。这种化合物可以形成准可逆的电化学自由基阳离子，而氧化电位则取决于噻吩所附电子基团的性质。电子推挽系统的晶体学数据显示，偶氮甲基键是平面和线性的，它们采用 E 异构体。