7-bromo-10-(2-decyltetradecyl)-10H-phenothiazine-3-carbaldehyde | 1370461-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 7-bromo-10-(2-decyltetradecyl)-10H-phenothiazine-3-carbaldehyde
• 英文别名: 7-Bromo-10-(2-decyltetradecyl)phenothiazine-3-carbaldehyde；7-bromo-10-(2-decyltetradecyl)phenothiazine-3-carbaldehyde
• CAS: 1370461-51-0
• 化学式: C₃₇H₅₆BrNOS
• 分子量: 642.828
• InChiKey: KKPCLYIXTUEUHI-UHFFFAOYSA-N

物化性质

• 沸点：
  692.9±55.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.7
• 重原子数：
  41
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-bromo-10-(2-decyltetradecyl)-10H-phenothiazine-3-carbaldehyde 在 copper(l) iodide 、 ammonium acetate 、 potassium carbonate 、 溶剂黄146 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 49.0h， 生成 (Z)-2-(5-((10-(2-decyltetradecyl)-7-(pyrrolidine-1-yl)-10H-phenothiazine-3-yl)-methylene)-4-oxo-2-thioxothiazolidine-3-yl)acetic acid
  参考文献：
  名称：

  Phenothiazinyl Rhodanylidene Merocyanines for Dye-Sensitized Solar Cells

  摘要：

  Phenothiazinyl rhodanylidene acetic acid merocyanine dyes with variable substitution pattern on the peripheral benzene ring were synthesized in good to excellent yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and rhodanine-N-acetic acid. The electronic properties were investigated by cyclic voltammetry, absorption, and fluorescence spectroscopy. Electron releasing substitution leads to an appreciable lowering of the oxidation potential, bathochromic shift of the absorption band, and minimization of the emission quantum yield. Not least as a consequence of these properties, the compounds are interesting for use as chromophores in dye-sensitized solar cells (DSSC). DSSCs were constructed and successfully tested by determining the characteristic parameters such as incident-photon-to-electron conversion efficiency (IPCE), fill factor (FF), and overall efficiency.

  DOI：

  10.1021/jo202608w
• 作为产物：
  描述：

  10-(2-decyltetradecyl)-10H-phenothiazine-3-carbaldehyde 在 溴 、 溶剂黄146 作用下， 反应 10.0h， 以88%的产率得到7-bromo-10-(2-decyltetradecyl)-10H-phenothiazine-3-carbaldehyde
  参考文献：
  名称：

  Phenothiazinyl Rhodanylidene Merocyanines for Dye-Sensitized Solar Cells

  摘要：

  Phenothiazinyl rhodanylidene acetic acid merocyanine dyes with variable substitution pattern on the peripheral benzene ring were synthesized in good to excellent yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and rhodanine-N-acetic acid. The electronic properties were investigated by cyclic voltammetry, absorption, and fluorescence spectroscopy. Electron releasing substitution leads to an appreciable lowering of the oxidation potential, bathochromic shift of the absorption band, and minimization of the emission quantum yield. Not least as a consequence of these properties, the compounds are interesting for use as chromophores in dye-sensitized solar cells (DSSC). DSSCs were constructed and successfully tested by determining the characteristic parameters such as incident-photon-to-electron conversion efficiency (IPCE), fill factor (FF), and overall efficiency.

  DOI：

  10.1021/jo202608w

文献信息

• Three-Component Suzuki–Knoevenagel Synthesis of Merocyanine Libraries and Correlation Analyses of Their Oxidation Potentials and Optical Band Gaps
  作者：Tim Meyer、Roxanne Krug、Thomas J. J. Müller

  DOI：10.3390/molecules26175149

  日期：——

  The Suzuki coupling Knoevenagel condensation one-pot synthesis of boronic acids/esters, (hetero)aromatic bromo aldehydes and methylene active compounds is a highly practical consecutive three-component process to provide substance libraries with 60 donor-π-bridge-acceptor molecules, i.e., merocyanines in a broader sense, in moderate to excellent yield. As already seen with the naked eye, a broad variation

  Suzuki 偶联 Knoevenagel 缩合一锅法合成硼酸/酯、（杂）芳族溴醛和亚甲基活性化合物是一种非常实用的连续三组分工艺，可提供具有 60 个供体-π-桥-受体分子的物质库，即，更广泛意义上的部花青，产量中等至极好。正如肉眼所见，使用这种实用的合成工具可以实现光学特性的广泛变化。更系统地，在绘制光学带隙与近亲系列氧化还原活性系统的第一氧化电位时的相关性分析提供了线性相关性，并且通过扩展，两个参数图（氧化电位和发射最大值）与光学带隙平面相关性。
• Synthesis and Photophysical Properties of Luminescent Phenothiazinyl Merocyanine Substituted Polyacetylenes
  作者：Wladislaw Pisetsky、Piotr Budny、Thomas J. J. Müller

  DOI：10.1002/anie.202316246

  日期：2024.1.22

  A series of soluble phenothiazinyl merocyanine substituted polyacetylenes have been readily synthesized by rhodium-catalyzed polymerization of the corresponding 3-ethynyl phenothiazines. These polyacetylenes with conjugatively ligated merocyanines are emissive in solution and in the solid state and also show emission solvatochromism.

  通过相应的3-乙炔基吩噻嗪的铑催化聚合，可以很容易地合成一系列可溶性吩噻嗪基部花青取代的聚乙炔。这些具有共轭连接的部花青的聚乙炔在溶液和固态下都具有发射性，并且还表现出发射溶剂化变色现象。
• Polyacetylenes with (hetero)aryl-, styryl-, and amino-phenothiazinyl sidechains: synthesis and photophysics
  作者：Wladislaw Pisetsky、Thomas J. J. Müller

  DOI：10.1039/d4ra01912a

  日期：——

  A novel generation of 7-aryl phenothiazinyl substituted polyacetylenes is readily accessible via controlled rhodium-catalyzed polymerization of the corresponding 3-ethynyl 7-aryl phenothiazines. The monomers are synthesized by Suzuki coupling, Heck coupling, or Buchwald–Hartwig amination, and Bestmann–Ohira reaction. This allows for the introduction of electron donating and releasing substituents with

  通过相应的3-乙炔基7-芳基吩噻嗪的受控铑催化聚合，可以容易地获得新一代7-芳基吩噻嗪基取代的聚乙炔。单体通过 Suzuki 偶联、Heck 偶联或 Buchwald-Hartwig 胺化以及 Bestmann-Ohira 反应合成。这允许引入具有不同连接模式的给电子和释放取代基。所得聚合物除极少数例外外均表现出窄分子量分布，并且可溶于许多有机溶剂。比较了新型单取代聚乙炔和相应单体的光物理性质。虽然单体在溶液中表现出强发射，量子产率高达 0.84，但只有选定的聚合物具有发光性（ Φ f = 0.06），并表现出适度的斯托克斯位移和正发射溶剂化变色现象。