1-(2-ethylhexyl)-2-vinyl-4,5-dicyanoimidazole | 936924-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-ethylhexyl)-2-vinyl-4,5-dicyanoimidazole
• 英文别名: 1-(2-ethylhexyl)-vinazene；2-Ethenyl-1-(2-ethylhexyl)imidazole-4,5-dicarbonitrile
• CAS: 936924-29-7
• 化学式: C₁₅H₂₀N₄
• 分子量: 256.351
• InChiKey: GUXCBGQPKLDNOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-二溴吡啶 、 1-(2-ethylhexyl)-2-vinyl-4,5-dicyanoimidazole 在 二(三叔丁基膦)钯 、 dicyclohexylmethylamine 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以44%的产率得到2-[2-[6-[2-[4,5-dicyano-1-(2-ethylhexyl)imidazol-2-yl]ethenyl]pyridin-3-yl]ethenyl]-1-(2-ethylhexyl)imidazole-4,5-dicarbonitrile
  参考文献：
  名称：

  Electron-Accepting Conjugated Materials Based on 2-Vinyl-4,5-dicyanoimidazoles for Application in Organic Electronics

  摘要：

  We report the Heck coupling of 2-vinyl-4,5-dicyanoimidazole (vinazene) with selected di- and trihalo aromatics in an effort to prepare linear and branched electron-accepting conjugated materials for application in organic electronics. By selecting the suitable halo-aromatic moiety, it is possible to tune the HOMO-LUMO energy levels, absorption, and emission properties for a specific application. In this regard, materials with strong photoluminescence from blue -> green -> red are reported that may have potential application in organic light-emitting diodes (OLEDs). Furthermore, derivatives with strong absorption in the-visible spectrum, coupled with favorable HOMO-LUMO levels, have been used to prepare promising organic photovoltaic devices (OPVs) when combined with commercially available semiconducting donor polymers.

  DOI：

  10.1021/jo802720m
• 作为产物：
  描述：

  2-vinyl-4,5-dicyanoimidazole 、 2-乙基碘己烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1-(2-ethylhexyl)-2-vinyl-4,5-dicyanoimidazole
  参考文献：
  名称：

  Solution processable bulk-heterojunction solar cells using a small molecule acceptor

  摘要：

  我们报道了一种基于2-乙烯基-4,5-二氰基咪唑（Vinazene™）的小分子电子受体，用于溶液处理的有机太阳能电池。该材料的最低未占分子轨道（LUMO）能级位于−3.6 eV，并在可见光谱范围内强吸收，直到520 nm——与广泛使用的受体（6,6）-苯基-C60-丁酸甲酯（PCBM）相比，具有吸引人的特点。该Vinazene衍生物与聚（2,7-咔唑）供体混合——该供体被选择是由于其互补的吸收范围及相对较高的最高占分子轨道（HOMO）能级（−5.6 eV）——并被纳入体材料异质结器件中。随后研究了供体/受体组成和退火温度对器件性能的影响。表现最佳的器件显示出合理的功率转换效率为0.75%，开路电压超过1.3 V，显著高于之前使用小分子受体的器件报告。

  DOI：

  10.1039/b813786m

文献信息

• N-type conjugated materials based on 2-vinyl-4,5-dicyanoimidazoles and their use in organic photovoltaics
  申请人：Sellinger Alan

  公开号：US20090032106A1

  公开（公告）日：2009-02-05

  There is provided novel n-type conjugated compounds based on 2-vinyl-4,5-dicyanoimidazole moieties conjugated via the vinyl group to an aromatic moiety. Also provided are thin films and photovoltaics comprising the novel compounds, as well as methods of synthesizing the compounds.

  提供了基于2-乙烯基-4,5-二氰基咪唑基团的新型n-型共轭化合物，通过乙烯基与芳香基团共轭连接。还提供了包含这些新型化合物的薄膜和光伏器件，以及合成这些化合物的方法。
• Electron-Accepting Conjugated Materials Based on 2-Vinyl-4,5-dicyanoimidazoles for Application in Organic Electronics
  作者：Richard Y. C. Shin、Prashant Sonar、Pei Sann Siew、Zhi-Kuan Chen、Alan Sellinger

  DOI：10.1021/jo802720m

  日期：2009.5.1

  We report the Heck coupling of 2-vinyl-4,5-dicyanoimidazole (vinazene) with selected di- and trihalo aromatics in an effort to prepare linear and branched electron-accepting conjugated materials for application in organic electronics. By selecting the suitable halo-aromatic moiety, it is possible to tune the HOMO-LUMO energy levels, absorption, and emission properties for a specific application. In this regard, materials with strong photoluminescence from blue -> green -> red are reported that may have potential application in organic light-emitting diodes (OLEDs). Furthermore, derivatives with strong absorption in the-visible spectrum, coupled with favorable HOMO-LUMO levels, have been used to prepare promising organic photovoltaic devices (OPVs) when combined with commercially available semiconducting donor polymers.
• Solution processable bulk-heterojunction solar cells using a small molecule acceptor
  作者：Zi En Ooi、Teck Lip Tam、Richard Yee Cheong Shin、Zhi Kuan Chen、Thomas Kietzke、Alan Sellinger、Martin Baumgarten、Klaus Mullen、John C. deMello

  DOI：10.1039/b813786m

  日期：——

  We report a small-molecule electron-acceptor based on 2-vinyl-4,5-dicyanoimidazole [Vinazene™] for use in solution processed organic solar cells. The material has a favourably located LUMO level of −3.6 eV and absorbs strongly in the visible spectrum up to 520 nm—attractive properties compared to the widely used acceptor (6,6)-phenyl-C60-butyric acid methyl ester (PCBM). The Vinazene derivative was blended with a poly(2,7-carbazole) donor—chosen for its complementary absorption range and comparatively high-lying HOMO level of −5.6 eV—and incorporated into bulk heterojunction devices. The influence of the donor/acceptor composition and annealing temperature on device performance were then investigated. The best performing devices exhibited reasonable power conversion efficiencies of 0.75% and open-circuit voltages of more than 1.3 V, substantially higher than previously reported devices using small molecule acceptors.

  我们报道了一种基于2-乙烯基-4,5-二氰基咪唑（Vinazene™）的小分子电子受体，用于溶液处理的有机太阳能电池。该材料的最低未占分子轨道（LUMO）能级位于−3.6 eV，并在可见光谱范围内强吸收，直到520 nm——与广泛使用的受体（6,6）-苯基-C60-丁酸甲酯（PCBM）相比，具有吸引人的特点。该Vinazene衍生物与聚（2,7-咔唑）供体混合——该供体被选择是由于其互补的吸收范围及相对较高的最高占分子轨道（HOMO）能级（−5.6 eV）——并被纳入体材料异质结器件中。随后研究了供体/受体组成和退火温度对器件性能的影响。表现最佳的器件显示出合理的功率转换效率为0.75%，开路电压超过1.3 V，显著高于之前使用小分子受体的器件报告。