10-hexyl-7-p-tolyl-10H-phenothiazine-3-carbaldehyde | 1334496-52-4

• 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: 10-hexyl-7-p-tolyl-10H-phenothiazine-3-carbaldehyde
• 英文别名: 10-Hexyl-7-(4-methylphenyl)phenothiazine-3-carbaldehyde；10-hexyl-7-(4-methylphenyl)phenothiazine-3-carbaldehyde
• CAS: 1334496-52-4
• 化学式: C₂₆H₂₇NOS
• 分子量: 401.572
• InChiKey: JTUWKCJRYONRLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  3-羧甲基绕丹宁 、 10-hexyl-7-p-tolyl-10H-phenothiazine-3-carbaldehyde 在 ammonium acetate 、 溶剂黄146 作用下， 反应 5.0h， 以67%的产率得到(Z)-2-(5-((10-hexyl-7-p-tolyl-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：

  吩噻嗪 在 四(三苯基膦)钯 、 potassium tert-butylate 、 溴 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 1,2-二氯乙烷 为溶剂， 反应 78.0h， 生成 10-hexyl-7-p-tolyl-10H-phenothiazine-3-carbaldehyde
  参考文献：
  名称：

  发射光变色酚噻嗪基花青染料的合成，电学和光电性质

  摘要：

  通过Knoevenagel缩合相应的吩噻嗪基醛与N-甲基罗丹宁或茚满-1,3-二酮，可以高收率合成在外围苯环上具有可变取代图形的吩噻嗪基部花青染料。通过循环伏安法，吸收法，电光吸收法和发射光谱法研究了电子性质。所有这些花青素都显示出可逆的氧化还原行为，该行为是由吩噻嗪基为中心的氧化产生稳定的自由基阳离子。的氧化还原电位与哈米特强烈相关σ p参数。所有花青素都显示出较大的斯托克斯位移。它们还显示出明显的发射溶剂变色现象，这是由从基态激发到激发态时大的偶极矩变化引起的。这些发现得到溶剂变色研究和与时间有关的DFT计算的支持。

  DOI：

  10.1002/chem.201100592

文献信息

• Synthesis, Electronic, and Electro-Optical Properties of Emissive Solvatochromic Phenothiazinyl Merocyanine Dyes
  作者：Martina Hauck、Matthias Stolte、Jan Schönhaber、Hans-Georg Kuball、Thomas J. J. Müller

  DOI：10.1002/chem.201100592

  日期：2011.8.29

  patterns on the peripheral benzene ring were synthesized in good yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and N‐methylrhodanine or indan‐1,3‐dione. The electronic properties were investigated by cyclic voltammetry, absorption, electro‐optical absorption, and emission spectroscopy. All these merocyanines reveal reversible redox behavior that stems from the phenothiazinyl‐centered

  通过Knoevenagel缩合相应的吩噻嗪基醛与N-甲基罗丹宁或茚满-1,3-二酮，可以高收率合成在外围苯环上具有可变取代图形的吩噻嗪基部花青染料。通过循环伏安法，吸收法，电光吸收法和发射光谱法研究了电子性质。所有这些花青素都显示出可逆的氧化还原行为，该行为是由吩噻嗪基为中心的氧化产生稳定的自由基阳离子。的氧化还原电位与哈米特强烈相关σ p参数。所有花青素都显示出较大的斯托克斯位移。它们还显示出明显的发射溶剂变色现象，这是由从基态激发到激发态时大的偶极矩变化引起的。这些发现得到溶剂变色研究和与时间有关的DFT计算的支持。
• 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.