N-(对甲基苯基)苯并吲哚 | 273220-33-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(对甲基苯基)苯并吲哚
• 中文别名: N-(4-甲基)苯基-1,2,3,3a,4,8b-六氢环戊基[b]吲哚
• 英文名称: 4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole
• 英文别名: 4-(p-Tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole；4-(4-methylphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indole
• CAS: 273220-33-0
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: UZFOEGFWKUBPHK-UHFFFAOYSA-N

物化性质

• 沸点：
  381.5±22.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-(对甲基苯基)苯并吲哚 在 sodium hydride 、 三氯氧磷 作用下， 反应 6.0h， 生成 4-(4-methylphenyl)-7-styryl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole
  参考文献：
  名称：

  Synthesis and characterization of triphenylamine modified azobenzene dyes

  摘要：

  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.

  DOI：

  10.1016/j.dyepig.2016.10.018
• 作为产物：
  描述：

  1,2,3,3a,4,8b-六氢环戊二烯并[b]吲哚 、 对溴甲苯 在 palladium diacetate 、 sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以70%的产率得到N-(对甲基苯基)苯并吲哚
  参考文献：
  名称：

  Unsymmetrical squaraines with new linkage manner for high-performance solution-processed small-molecule organic photovoltaic cells

  摘要：

  两种非对称的方醌类化合物被用作高性能BHJ-OPV器件的供体，其光电流密度（Jsc）大于13 mA/cm²，光电转换效率（PCE）大于5%。

  DOI：

  10.1039/c5ra24186c

文献信息

• 一种芳香族哒嗪类化合物、制备方法及应用
  申请人：天津大学

  公开号：CN111434651B

  公开（公告）日：2023-08-22

  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。
• Unsymmetrical squaraines with new linkage manner for high-performance solution-processed small-molecule organic photovoltaic cells
  作者：Lin Yang、Daobin Yang、Yao Chen、Qian Luo、Mangang Zhang、Yan Huang、Zhiyun Lu、Hisahiro Sasabe、Junji Kido

  DOI：10.1039/c5ra24186c

  日期：——

  Two unsymmetrical squaraines were employed as donors for high performance BHJ-OPV devices with J_sc > 13 mA cm⁻² and PCE > 5%.

  两种非对称的方醌类化合物被用作高性能BHJ-OPV器件的供体，其光电流密度（Jsc）大于13 mA/cm²，光电转换效率（PCE）大于5%。
• Di-thiazolyl-benzodiazole based sensitizers and their use in photovoltaic cell
  申请人：Karim Mohammad Rezaul

  公开号：US08575355B2

  公开（公告）日：2013-11-05

  Described herein are D-π-A type sensitizers of the formula (I) or (II) having a novel central π-conjugated unit di-thiazolyl-benzodiazole and dye-sensitized electrodes including a substrate having an electrically conductive surface, an oxide semiconductor film formed on the conductive surface, and the above sensitizer of formula (I) or (II), as specified above, supported on the film. A solar cell includes the above electrode, a counter electrode, and an electrolyte deposited there between. The sensitizers of formula (I) and (II) efficiently sensitize the semiconductor materials and show a high solar to electricity conversion efficiency.

  本文描述了具有新型中心π-共轭单元二噻唑基苯并二氮杂苯的D-π-A型敏化剂的化学式(I)或(II)，以及包括具有电导表面的基底、在导电表面上形成的氧化物半导体薄膜以及上述化学式(I)或(II)中的敏化剂，所述敏化剂支持在薄膜上的染料敏化电极。太阳能电池包括上述电极、对电极和在其之间沉积的电解质。化学式(I)和(II)的敏化剂有效地敏化半导体材料，并显示出较高的太阳能转换效率。
• Donor–acceptor dyes incorporating a stable dibenzosilole π-conjugated spacer for dye-sensitized solar cells
  作者：Md. Akhtaruzzaman、Yohei Seya、Naoki Asao、Ashraful Islam、Eunsang Kwon、Ahmed El-Shafei、Liyuan Han、Yoshinori Yamamoto

  DOI：10.1039/c2jm30978e

  日期：——

  Four novel organic dyes including three based on dibenzosilole (YS01–03) and one based on fluorene (YS04) were synthesized, and their photophysical properties and dye-sensitized solar cell (DSC) performances were characterized. The silicon-containing dibenzosilole-based dyes (YS01–03) were superior to the carbon analogue fluorene-based dye YS04 in incident-photon-to-current conversion efficiency (IPCE), and total solar-to-electric conversion efficiency (η), with YS03, which has the bulkiest and most branched electron donor group, achieving the highest η of 5.07% compared to 2.88% of YS04. To better understand how silicon influences the excited state oxidation potentials (S+/*) and absorption maxima (λmax), the equilibrium molecular geometries of dyes YS01–04 were calculated using density functional theory (DFT) utilizing B3LYP energy functional and DGDZVP basis set. It was shown that the torsion angles (θ1 and θ2) across the biphenyl linkages of dyes containing silicon (YS01–03) were less twisted than that of the silicon-free dye (YS04), which enhanced the π–π* overlap, and that translated into photocurrent enhancements in the silicon-containing dyes YS01–03. Moreover, the vertical electronic excitations and S+/* of dyes YS01–04 were studied using different long-range corrected time-dependent DFT methods, including CAM-B3LYP, LC-BLYP, WB97XD, and LC-wPBE at the basis set level DGDZVP. Excellent agreement between the calculated, using CAM-B3LYP/DGDZVP, and experimental results was found.

  合成了四种新型有机染料，包括三种基于二苯并硅啶（YS01–03）和一种基于萘的染料（YS04），并对其光物理特性和染料敏化太阳能电池（DSC）的性能进行了表征。含硅的二苯并硅啶基染料（YS01–03）在入射光子转电流效率（IPCE）和总太阳能转电能效率（η）方面优于碳基类似物的萘基染料（YS04），其中YS03具有最大体积和最为分支的电子给体基团，实现了最高的η值为5.07%，而YS04的η值仅为2.88%。为了更好地理解硅如何影响激发态氧化电位（S+/*）和吸收最大值（λmax），利用密度泛函理论（DFT）计算了染料YS01–04的平衡分子几何结构，采用B3LYP能量泛函和DGDZVP基组。结果表明，含硅染料（YS01–03）中通过联苯链接的扭转角（θ1和θ2）比不含硅的染料（YS04）扭转程度更小，从而增强了π–π*重叠，这转化为含硅染料YS01–03中的光电流增强。此外，通过不同的长程校正时间相关DFT方法，包括CAM-B3LYP、LC-BLYP、WB97XD和LC-wPBE，研究了染料YS01–04的垂直电子激发和S+/*。使用CAM-B3LYP/DGDZVP计算的结果与实验结果之间具有很好的吻合。
• D–A–π–A featured sensitizers by modification of auxiliary acceptor for preventing “trade-off” effect
  作者：Haibo Zhu、Bo Liu、Jingchuan Liu、Weiwei Zhang、Wei-Hong Zhu

  DOI：10.1039/c5tc01195g

  日期：——

  The two thiophene groups grafted onto the auxiliary quinoxaline acceptor successfully overcome the unfavorable “trade-off” effect between the photocurrent and photovoltage.

  附加的喹啉受体上移植的两个噻吩基团成功地克服了光电流和光电压之间不利的“权衡”效应。