7,7,8,8-tetracyano-p-quinodimethanepropanoic acid | 87145-82-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 7,7,8,8-tetracyano-p-quinodimethanepropanoic acid
• 英文别名: 3-[3,6-Bis(dicyanomethylene)-1,4-cyclohexadien-1-yl]propanoic acid；3-[3,6-bis(dicyanomethylidene)cyclohexa-1,4-dien-1-yl]propanoic acid
• CAS: 87145-82-2
• 化学式: C₁₅H₈N₄O₂
• 分子量: 276.254
• InChiKey: XJIFHQLJZZMWML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,7,8,8-tetracyano-p-quinodimethanepropanoic acid 在 正丁基锂 、 草酰氯 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 72.0h， 生成 3-(3,6-Bis-dicyanomethylene-cyclohexa-1,4-dienyl)-propionic acid 5-methyl-4',5'-dipentyl-[2,2']bi[[1,3]dithiolylidene]-4-ylmethyl ester
  参考文献：
  名称：

  共价四硫富瓦烯-四氰基喹二甲烷二元共聚物：极低的HOMO-LUMO间隙，热激发电子转移和高质量的langmuir-blodgett膜。

  摘要：

  DOI：

  10.1002/anie.200351876
• 作为产物：
  描述：

  3-<2,5-bis(dicyanomethylene)cyclohexyl>propanoic acid 在 manganese(IV) oxide 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以42%的产率得到7,7,8,8-tetracyano-p-quinodimethanepropanoic acid
  参考文献：
  名称：

  Organic metals. Preparation and properties of 7,7,8,8-tetracyano-p-quinodimethaneacetic and -propanoic acids

  摘要：

  DOI：

  10.1021/jo00169a063

文献信息

• Far-red absorbing squarylium dyes with terminally connected electron-accepting units for organic dye-sensitized solar cells
  作者：Takeshi Maeda、Hidekazu Nakao、Hisashi Kito、Hirokazu Ichinose、Shigeyuki Yagi、Hiroyuki Nakazumi

  DOI：10.1016/j.dyepig.2011.01.006

  日期：2011.9

  Novel squarylium dyes with either terminally placed tetracyanoquinodimethane or tetracyanoanthraquinodimethane moieties as strong electron acceptors were designed and synthesized for use as sensitizers for TiO2-based dye-sensitized solar cells (DSSCs). The photovoltaic performance of DSSCs indicates that two chromophores, strong electron acceptors and squarylium components, make independent contributions to photosensitization of nanocrystalline TiO2. DSSCs fabricated from squarylium-based diads as sensitizers and chenodeoxycholic acid as the coadsorbent exhibited a high open-circuit voltage (up to 0.66 V), suggesting that the electron-accepting components showed some effect on electron injection from the squarylium chromophore to the conduction band of TiO2. Under the coadsorbent-free conditions, the short-circuit photocurrent and overall solar-to-electrical energy conversion efficiency of the photovoltaic cells was improved by the contribution of photosensitizing effect in the wavelength range derived from the electron-acceptor components rather than the squarylium component. This phenomenon implies the possibility that the electron-accepting group acts as an anchoring unit to the TiO2 surface. (C) 2011 Elsevier Ltd. All rights reserved.
• BAGHDADCHI, J.;PANETTA, C. A., J. ORG. CHEM., 1983, 48, N 21, 3852-3854
  作者：BAGHDADCHI, J.、PANETTA, C. A.

  DOI：——

  日期：——
• Organic metals. Preparation and properties of 7,7,8,8-tetracyano-p-quinodimethaneacetic and -propanoic acids
  作者：Jamil Baghdadchi、Charles A. Panetta

  DOI：10.1021/jo00169a063

  日期：1983.10
• A Covalent Tetrathiafulvalene–Tetracyanoquinodimethane Diad: Extremely Low HOMO–LUMO Gap, Thermoexcited Electron Transfer, and High-Quality Langmuir–Blodgett Films
  作者：Dmitrii F. Perepichka、Martin R. Bryce、Christopher Pearson、Michael C. Petty、Eric J. L. McInnes、Jing P. Zhao

  DOI：10.1002/anie.200351876

  日期：2003.10.6