1-(2-ethylhexyl)-indole-3-carboxaldehyde | 441070-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(2-ethylhexyl)-indole-3-carboxaldehyde
• 英文别名: 1-(2-ethylhexyl)indole-3-carbaldehyde
• CAS: 441070-89-9
• 化学式: C₁₇H₂₃NO
• mdl: MFCD21402792
• 分子量: 257.376
• InChiKey: FFYFSAVGWZBFOT-UHFFFAOYSA-N

物化性质

• 沸点：
  399.1±15.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-ethylhexyl)-indole-3-carboxaldehyde 在 N-甲基哌嗪 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 碘 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-[2-(2,4-Difluorophenyl)ethynyl]-1-(2-ethylhexyl)indole-3-carbaldehyde
  参考文献：
  名称：

  Thermally Induced Defluorination during a mer to fac Transformation of a Blue-Green Phosphorescent Cyclometalated Iridium(III) Complex

  摘要：

  The new homoleptic tris-cyclometalated [Ir((CN)-N-boolean AND)(3)] complexes mer-8, fac-8, and fac-9 incorporating gamma-carboline ligands are reported. Reaction of 3-(2,4-difluorophenyl)-5-(2-ethylhexyl)-pyrido[4,3-b]indole 6 with iridium(III) chloride under standard cyclometalating conditions gave the homoleptic complex mer-8 in 63% yield. The X-ray crystal structure of mer-8 is described. The Ir-C and Ir-N bonds show the expected bond length alternations for the differing trans influence of phenyl and pyridyl ligands. mer-8 quantitatively isomerized to fac-8 upon irradiation with UV light. However, heating mer-8 at 290 degrees C in glycerol led to an unusual regioselective loss of one fluorine atom from each of the ligands, yielding fac-9 in 58% yield. fac-8 is thermally very stable: no decomposition was observed when fac-8 was heated in glycerol at 290 degrees C for 48 h. The gamma-carboline system of fac-8 enhances thermal stability compared to the pyridyl analogue fac-Ir(46dfppy)(3) 10, which decomposes extensively upon being heated in glycerol at 290 degrees C for 2 h. Complexes mer-8, fac-8, and fac-9 are emitters of blue-green light (lambda(em)(max) = 477, 476, and 494 nm, respectively). The triplet lifetimes for fac-8 and fac-9 are similar to 4.5 Its at room temperature; solution On values are 0.31 and 0.22, respectively.

  DOI：

  10.1021/ic201655n
• 作为产物：
  描述：

  溴代异辛烷 、 3-吲哚甲醛 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以79%的产率得到1-(2-ethylhexyl)-indole-3-carboxaldehyde
  参考文献：
  名称：

  The effect of the molecular structure of the chromophore on the photorefractive properties of the polymer systems with low glass transition temperatures

  摘要：

  通过不同的共轭桥，如多烯、噻吩、吲哚和苯，与强电子给体和电子受体基团结合，合成了七种具有不同偶极矩和极化各向异性的发色团。在 70 V µm−1 电场下，观察到含有 30 wt% 发色团的光折变材料的双折射率在 0.45 × 10−3 至 5.0 × 10−3 范围内，具体取决于发色团结构。含有多烯基发色团的光折变材料表现出最高的光折变性能，其次是含有噻吩基、苯基和吲哚基发色团的光折变材料。据观察，在本研究中使用的材料系统中，宾主系统的光折射特性与取向双折射成线性比例。

  DOI：

  10.1039/b105555k

文献信息

• The preparation and properties of bulk-heterojunction organic solar cells with indole-containing fulleropyrrolidine derivatives as acceptors
  作者：Xiaona Zhang、Liang Sun、Wei Zheng、Xichang Bao、Ning Wang、Ting Wang、Renqiang Yang

  DOI：10.1016/j.tet.2013.09.046

  日期：2013.11

  Two indole-containing fullerene derivatives, N-hydrogen-2-[3-(N-2-ethylhexylindolyl)][60]fulleropyrrolidine (EHIHC60P), and N-(2-ethylhexylindolyl))-2-[3-(N-2-ethylhexylindoly1)][60]fulleropyrrolidine (DEHIC60P) were synthesized by the typical Prato reaction. The absorption spectra, electrochemical properties of the two compounds were measured. Inverted solar cells were fabricated with the structure of ITO/ZnO/poly(3-hexylthiophene) (P3HT):fullerene derivatives/MoO3/Ag. The highest power conversion efficiencies (PCEs) of 3.32% and 3.23% were obtained for P3HT/EHIHC60P and P3HT/DEHIC60P based solar cells at the composite ratio of 1:1 after the active layers were annealed at 150 degrees C under inert atmosphere, with a open-circuit voltage (V-oc) of 0.66 V and 0.74 V, respectively. For comparison, the device based on P3HT/PCBM at the same conditions showed the PCE of 328%, with a V-oc of 0.61 V. The influence on the photovoltaic property of the fullerene derivatives, which was induced by some subtle changes in the chemical structure was compared and discussed. (c) 2013 Elsevier Ltd. All rights reserved.