10-(2-decyltetradecyl)-10H-[3,10'-biphenothiazine]-7-carbaldehyde | 1370461-53-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 10-(2-decyltetradecyl)-10H-[3,10'-biphenothiazine]-7-carbaldehyde
• 英文别名: 10-(2-Decyltetradecyl)-7-phenothiazin-10-ylphenothiazine-3-carbaldehyde；10-(2-decyltetradecyl)-7-phenothiazin-10-ylphenothiazine-3-carbaldehyde
• CAS: 1370461-53-2
• 化学式: C₄₉H₆₄N₂OS₂
• 分子量: 761.192
• InChiKey: UNSGTYSOBDRORT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.4
• 重原子数：
  54
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-羧甲基绕丹宁 、 10-(2-decyltetradecyl)-10H-[3,10'-biphenothiazine]-7-carbaldehyde 在 ammonium acetate 、 溶剂黄146 作用下， 反应 5.0h， 以94%的产率得到(Z)-2-(5-((10-(2-decyltetradecyl)-10H,10'H-3,10'-biphenothiazine-7-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 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 生成 10-(2-decyltetradecyl)-10H-[3,10'-biphenothiazine]-7-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

• 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：2024.3.26

  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。
• Phenothiazinyl Rhodanylidene Merocyanines for Dye-Sensitized Solar Cells
  作者：Tim Meyer、Daniel Ogermann、Andrea Pankrath、Karl Kleinermanns、Thomas J. J. Müller

  DOI：10.1021/jo202608w

  日期：2012.4.20

  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.