(E)-2-cyano-3-(N-hexylphenothiazin-7-yl)acrylic acid | 1352937-87-1

• 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: (E)-2-cyano-3-(N-hexylphenothiazin-7-yl)acrylic acid
• 英文别名: (E)-2-cyano-3-(10-hexylphenothiazin-3-yl)prop-2-enoic acid
• CAS: 1352937-87-1
• 化学式: C₂₂H₂₂N₂O₂S
• 分子量: 378.495
• InChiKey: CANKEDAOOHMFEZ-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  溴己烷 在 potassium tert-butylate 、 ammonium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 24.33h， 生成 (E)-2-cyano-3-(N-hexylphenothiazin-7-yl)acrylic acid
  参考文献：
  名称：

  Phenothiazine derivatives as organic sensitizers for highly efficient dye-sensitized solar cells

  摘要：

  合成了一系列含有苯噻嗪中心单元的有机染料，并有效地用于染料敏化太阳能电池（DSSCs）的制造。在苯噻嗪的C(3)位点添加了一种氰基丙烯酸酯部分作为电子受体，同时在C(7)位点连接了三芳胺部分作为电子给体。使用这些染料制作的DSSC在AM 1.5太阳条件下（100 mW cm−2）显示出显著的量子效率，范围为4.2%至6.2%。在苯噻嗪的N(10)位点添加了多种取代基，如甲基、己基和三苯胺基，以优化入射光子到电流的转换效率。在主要染料上还在不同位置插入了噻吩苯基，以研究其对器件性能的影响。最佳表现发现于化合物NSPt-C6，其中在苯噻嗪的N(10)位点连接了己基，并在C(7)位点连接了噻吩苯基。它显示出短路电流（Jsc）为14.42 mA cm−2，开路电压（Voc）为0.69 V，填充因子（ff）为0.63，相应的整体转换效率为6.22%。借助时间相关密度泛函理论（TDDFT）模型与B3LYP泛函分析了它们的光物理性质。通过电化学阻抗谱进一步阐明了它们的光伏行为。

  DOI：

  10.1039/c2jm13961h

文献信息

• Organic dyes containing oligo-phenothiazine for dye-sensitized solar cells
  作者：Yuan Jay Chang、Po-Ting Chou、Yan-Zuo Lin、Motonori Watanabe、Chih-Jen Yang、Tsung-Mei Chin、Tahsin J. Chow

  DOI：10.1039/c2jm35556f

  日期：——

  A series of organic dyes containing oligo-phenothiazine were synthesized and used effectively on the fabrication of dye-sensitized solar cells (DSSCs). In these compounds the phenothiazine moiety functions both as an electron donor and as a π-bridge. These materials exhibit considerably high values of open-circuit voltage (Voc) ranging from 0.78–0.83 V under an AM1.5 solar condition (100 mW cm−2). Two kinds of substituents, i.e., hexyl and hexyloxyphenyl groups, were added onto the N(10) of phenothiazine for comparison. The best device displayed a short-circuit current (Jsc) of 14.3 mA cm−2, an open-circuit voltage (Voc) of 0.83 V, a fill factor (FF) of 0.65, corresponding to an overall conversion efficiency of 7.78%. Their photophysical properties were analyzed with the aid of a time-dependent density functional theory (TDDFT) model with the B3LYP functional. The electronic nature of the devices was further elucidated by using electrochemical impedance spectroscopy.

  合成了一系列含有寡聚苯噻嗪的有机染料，并有效地用于染料敏化太阳能电池（DSSCs）的制造。在这些化合物中，苯噻嗪基团既作为电子给体，又作为π-桥。这些材料在AM1.5太阳条件（100 mW cm−2）下表现出相当高的开路电压（Voc），值范围为0.78–0.83 V。为了比较，两个种类的取代基，即己基和己氧基苯基，被添加到苯噻嗪的N(10)上。最佳器件显示短路电流（Jsc）为14.3 mA cm−2，开路电压（Voc）为0.83 V，填充因子（FF）为0.65，对应的整体转换效率为7.78%。使用带有B3LYP功能的时间依赖密度泛函理论（TDDFT）模型分析了它们的光物理特性。通过使用电化学阻抗谱进一步阐明了器件的电子性质。
• Phenothiazine derivatives as organic sensitizers for highly efficient dye-sensitized solar cells
  作者：Chih-Jen Yang、Yuan Jay Chang、Motonori Watanabe、Yung-Son Hon、Tahsin J. Chow

  DOI：10.1039/c2jm13961h

  日期：——

  A series of organic dyes containing a phenothiazine central unit were synthesized and were used effectively in the fabrication of dye-sensitized solar cells (DSSCs). A cyanoacrylate moiety was added at the C(3) position of the phenothiazine as an electron acceptor, and a triarylamine moiety was attached at the C(7) position as an electron donor. The DSSCs made with these dyes displayed remarkable quantum efficiency, ranging from 4.2–6.2% under an AM 1.5 solar condition (100 mW cm−2). A variety of substituents, i.e., methyl, hexyl and triphenylamino groups, were added at the N(10) of phenothiazine in order to optimize the incident photon-to-current conversion efficiency. Along the main chromophore a thiophenylene group was inserted at different positions to examine its influence on the properties of devices. The best performance was found in compound NSPt-C6, in which a hexyl group was attached at the N(10) of phenothiazine and a thiophenylene at the C(7) position. It displayed a short-circuit current (Jsc) of 14.42 mA cm−2, an open-circuit voltage (Voc) of 0.69 V, and a fill factor (ff) of 0.63, corresponding to an overall conversion efficiency of 6.22%. Their photophysical properties were analyzed with the aid of a time-dependent density functional theory (TDDFT) model with the B3LYP functional. Their photovoltaic behavior was further elucidated by the electrochemical impedance spectroscopy.

  合成了一系列含有苯噻嗪中心单元的有机染料，并有效地用于染料敏化太阳能电池（DSSCs）的制造。在苯噻嗪的C(3)位点添加了一种氰基丙烯酸酯部分作为电子受体，同时在C(7)位点连接了三芳胺部分作为电子给体。使用这些染料制作的DSSC在AM 1.5太阳条件下（100 mW cm−2）显示出显著的量子效率，范围为4.2%至6.2%。在苯噻嗪的N(10)位点添加了多种取代基，如甲基、己基和三苯胺基，以优化入射光子到电流的转换效率。在主要染料上还在不同位置插入了噻吩苯基，以研究其对器件性能的影响。最佳表现发现于化合物NSPt-C6，其中在苯噻嗪的N(10)位点连接了己基，并在C(7)位点连接了噻吩苯基。它显示出短路电流（Jsc）为14.42 mA cm−2，开路电压（Voc）为0.69 V，填充因子（ff）为0.63，相应的整体转换效率为6.22%。借助时间相关密度泛函理论（TDDFT）模型与B3LYP泛函分析了它们的光物理性质。通过电化学阻抗谱进一步阐明了它们的光伏行为。