4-(4-甲基苯基)-1,2,3,3a,4,8b-六氢环戊并[b]吲哚-7-甲醛 | 273220-35-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(4-甲基苯基)-1,2,3,3a,4,8b-六氢环戊并[b]吲哚-7-甲醛
• 英文名称: 4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole-7-carbaldehyde
• 英文别名: 4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopentadieno[b]indole-7-carbaldehyde；4-(4-methylphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indole-7-carbaldehyde
• CAS: 273220-35-2
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: ZOZFBOVFKXAQIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-(4-甲基苯基)-1,2,3,3a,4,8b-六氢环戊并[b]吲哚-7-甲醛 在 potassium tert-butylate 、 lithium acetate 、 四丁基溴化铵 、 palladium diacetate 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成
  参考文献：
  名称：

  一种芳香族哒嗪类化合物、制备方法及应用

  摘要：

  本发明公开了一种芳香族哒嗪类化合物，并采用1H‑NMR等方式对其进行表征，该化合物具有较长的电荷分离态寿命，可以作为较好的光电材料。另外本发明还提供一种芳香族哒嗪类化合物的制备方法，该制备方法环境友好、操作便捷。该方法分为三步：步骤1，以2,4‑二溴硝基苯为原料通过偶联反应制得5,5‑二溴‑2,2’‑二硝基联苯；步骤2，以R1基取代的乙烯衍生物和5,5‑二溴‑2,2’‑二硝基联苯为原料通过偶联反应合成硝基取代化合物；步骤3：以所述硝基取代化合物为原料通过还原反应合成芳香族哒嗪类化合物。本发明还公开了一种芳香族哒嗪类化合物在太阳能电池中的应用和一种芳香族哒嗪类化合物在pH检测中的应用。

  公开号：

  CN111434651B
• 作为产物：
  描述：

  N-(对甲基苯基)苯并吲哚 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 0.5h， 以50%的产率得到4-(4-甲基苯基)-1,2,3,3a,4,8b-六氢环戊并[b]吲哚-7-甲醛
  参考文献：
  名称：

  一种芳香族哒嗪类化合物、制备方法及应用

  摘要：

  本发明公开了一种芳香族哒嗪类化合物，并采用1H‑NMR等方式对其进行表征，该化合物具有较长的电荷分离态寿命，可以作为较好的光电材料。另外本发明还提供一种芳香族哒嗪类化合物的制备方法，该制备方法环境友好、操作便捷。该方法分为三步：步骤1，以2,4‑二溴硝基苯为原料通过偶联反应制得5,5‑二溴‑2,2’‑二硝基联苯；步骤2，以R1基取代的乙烯衍生物和5,5‑二溴‑2,2’‑二硝基联苯为原料通过偶联反应合成硝基取代化合物；步骤3：以所述硝基取代化合物为原料通过还原反应合成芳香族哒嗪类化合物。本发明还公开了一种芳香族哒嗪类化合物在太阳能电池中的应用和一种芳香族哒嗪类化合物在pH检测中的应用。

  公开号：

  CN111434651B

文献信息

• Molecular engineering and theoretical investigation of organic sensitizers based on indoline dyes for quasi-solid state dye-sensitized solar cells
  作者：Bo Liu、Wenjun Wu、Xiaoyan Li、Lei Li、Shaofu Guo、Xiaoru Wei、Weihong Zhu、Qingbin Liu

  DOI：10.1039/c1cp20484j

  日期：——

  Novel indoline dyes, I-1–I-4, with structural modification of π-linker group in the D-π-A system have been synthesized and fully characterized. Molecular engineering through expanding the π-linker segment has been performed. The ground and excited state properties of the dyes have been studied by means of density functional theory (DFT) and time-dependent DFT (TD-DFT). Larger π-conjugation linkers would lead to broader spectral response and higher molar extinction coefficient but would decrease dye-loaded amount on TiO2 electrode and LUMO level. While applied in DSSCs, the variation trends in short-circuit current density (Jsc) and open-circuit voltage (Voc) were observed to be opposite to each other. The internal reasons were studied by experimental data and theoretical calculations in detail. Notably, I-2 showed comparable photocurrent values with liquid and quasi-solid state electrolyte, which suggested through molecular engineering of organic sensitizers the dilemma between optical absorption and charge diffusion lengths can be balanced well. Through studies of photophysical, electrochemical, and theoretical calculation results, the internal relations between chemical structure and efficiency have been revealed, which serve to enhance our knowledge regarding design and optimization of new sensitizers for quasi-solid state DSSCs, providing a powerful strategy for prediction of photovoltaic performances.

  新型吲哚啉染料 I-1-I-4（在 D-π-A 系统中对π-连接基团进行了结构调整）已被合成并充分表征。研究人员通过扩大π-连接基段进行了分子工程。通过密度泛函理论（DFT）和时间相关 DFT（TD-DFT）研究了染料的基态和激发态特性。较大的π-共轭连接体会导致更宽的光谱响应和更高的摩尔消光系数，但会降低二氧化钛电极上的染料负载量和LUMO水平。在应用于 DSSC 时，短路电流密度（Jsc）和开路电压（Voc）的变化趋势是相反的。实验数据和理论计算详细研究了其内在原因。值得注意的是，I-2 在液态和准固态电解质中显示出相当的光电流值，这表明通过有机敏化剂的分子工程，可以很好地平衡光吸收和电荷扩散长度之间的矛盾。通过对光物理、电化学和理论计算结果的研究，揭示了化学结构与效率之间的内在联系，有助于提高我们对准固态 DSSC 新敏化剂的设计和优化的认识，为预测光伏性能提供了有力的策略。
• Organic dye, photoelectric transducing material, semiconductor electrode, and photoelectric transducing device
  申请人：Mitsubishi Paper Mills Limited

  公开号：EP1997855A2

  公开（公告）日：2008-12-03

  Disclosed are an organic dye having a specific structure, a photoelectric conversion material containing the dye, a semiconductor electrode formed of a substrate having an electrically conductive surface, a semiconductor layer coated on the electrically conductive surface and the above dye adsorbed on the surface, and a photoelectric conversion device to which the above dye is applied. The present invention uses the above dye and can therefore provide a photoelectric conversion device excellent in photoelectric conversion efficiency, and the photoelectric conversion device is suitable for use in a solar cell or the like.

  本发明公开了一种具有特定结构的有机染料，一种含有该染料的光电转换材料，一种由具有导电表面的基板、涂覆在导电表面上的半导体层和吸附在该表面上的上述染料构成的半导体电极，以及一种应用了上述染料的光电转换装置。 本发明使用了上述染料，因此可以提供一种光电转换效率极佳的光电转换装置，该光电转换装置适用于太阳能电池等。
• Synthesis and characterization of triphenylamine modified azobenzene dyes
  作者：Chuanwu Zhao、Tianyang Wang、Dongmei Li、Ting Lu、Dongzhi Liu、Qingbo Meng、Qianqian Zhang、Fengqing Li、Wei Li、Wenping Hu、Lichang Wang、Xueqin Zhou

  DOI：10.1016/j.dyepig.2016.10.018

  日期：2017.2

  A series of triphenylamine modified azobenzenes were synthesized and studied theoretically and experimentally. D-A-D structures of these dyes were revealed with an intramolecular charge transfer (ICT) from both triphenylamine or indoline units (donor) to the central azobenzene unit (acceptor). Both computational and experimental results indicate that a stronger electron donating ability of the donor enhances the degree of ICT and improve their HOMO energies. The absorption spectra indicate an increased light absorption by enhanced ICT effect. The intermolecular interaction also affects their absorption ability. The strongest intermolecular interaction results in the best light absorption ability in films. An obviously increased hole mobility was also found as the ICT was-enhanced. These dyes were used as hole transport materials (HTM) of perovskite solar cells to investigate their feasibility. It is revealed that the solubility and filming ability are significant for the photovoltaic performance of devices. (C) 2016 Elsevier Ltd. All rights reserved.
• ORGANIC DYE, PHOTOELECTRIC TRANSDUCING MATERIAL, SEMICONDUCTOR ELECTRODE, AND PHOTOELECTRIC TRANSDUCING DEVICE
  申请人：MITSUBISHI PAPER MILLS LIMITED

  公开号：EP1526159B1

  公开（公告）日：2010-06-16
• Organic dye, photoelectric conversion material, semiconductor electrode and photoelectric conversion device
  申请人：Horiuchi Tamotsu

  公开号：US20080149175A1

  公开（公告）日：2008-06-26

  Disclosed are an organic dye having a specific structure, a photoelectric conversion material containing the dye, a semiconductor electrode formed of a substrate having an electrically conductive surface, a semiconductor layer coated on the electrically conductive surface and the above dye adsorbed on the surface, and a photoelectric conversion device to which the above dye is applied. The present invention uses the above dye and can therefore provide a photoelectric conversion device excellent in photoelectric conversion efficiency, and the photoelectric conversion device is suitable for use in a solar cell or the like.