2-((2-butoxy-3,4-dioxocyclobut-1-en-1-yl)methylene)-1-ethyl-3,3-dimethylindoline-5-carboxylic acid | 1425382-28-0

• 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: 2-((2-butoxy-3,4-dioxocyclobut-1-en-1-yl)methylene)-1-ethyl-3,3-dimethylindoline-5-carboxylic acid
• CAS: 1425382-28-0
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: IUVQIUPZSUAPJD-UHFFFAOYSA-N

物化性质

• 熔点：
  244 °C (decomp)
• 沸点：
  539.9±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((2-butoxy-3,4-dioxocyclobut-1-en-1-yl)methylene)-1-ethyl-3,3-dimethylindoline-5-carboxylic acid 、 1-hexyl-2-methylbenz[c,d]indolium perchlorate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 、 甲苯 、 正丁醇 为溶剂， 反应 18.5h， 以27%的产率得到4-[(5-Carboxy-1-ethyl-3,3-dimethylindol-1-ium-2-yl)methylidene]-2-[(1-hexylbenzo[cd]indol-2-ylidene)methyl]-3-oxocyclobuten-1-olate
  参考文献：
  名称：

  Effect of extended π-conjugation on photovoltaic performance of dye sensitized solar cells based on unsymmetrical squaraine dyes

  摘要：

  Aiming toward the far-red to near infra-red (NIR) photon harvesting, three new unsymmetrical squaraine dyes bearing direct ring carboxy functionalized indole as an anchoring moiety with varying donor groups with extended pi-conjugation have been successfully synthesized and utilized for dye sensitized solar cell fabrication. Under simulated solar irradiation, dye SQ-8 gave a photoconversion efficiency of 3.3% mainly harvesting photons in the far-red region between 500 and 700 nm. By extending the pi-conjugation of the donor moieties in the novel unsymmetrical squaraine dyes, it was possible to extend the light absorption from far-red to NIR wavelength region. In spite of good light absorption up to 900 nm and energetic matching, dye SQ-16 was found to exhibit the decreased photon harvesting, which was explained by the enhanced dye aggregation along with its difficulty in facile electron injection as indicated from electronic absorption spectroscopic and DFT calculation results, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.036
• 作为产物：
  描述：

  方酸二正丁酯 、 5-carboxy-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 1.0h， 以48%的产率得到2-((2-butoxy-3,4-dioxocyclobut-1-en-1-yl)methylene)-1-ethyl-3,3-dimethylindoline-5-carboxylic acid
  参考文献：
  名称：

  Effect of extended π-conjugation on photovoltaic performance of dye sensitized solar cells based on unsymmetrical squaraine dyes

  摘要：

  Aiming toward the far-red to near infra-red (NIR) photon harvesting, three new unsymmetrical squaraine dyes bearing direct ring carboxy functionalized indole as an anchoring moiety with varying donor groups with extended pi-conjugation have been successfully synthesized and utilized for dye sensitized solar cell fabrication. Under simulated solar irradiation, dye SQ-8 gave a photoconversion efficiency of 3.3% mainly harvesting photons in the far-red region between 500 and 700 nm. By extending the pi-conjugation of the donor moieties in the novel unsymmetrical squaraine dyes, it was possible to extend the light absorption from far-red to NIR wavelength region. In spite of good light absorption up to 900 nm and energetic matching, dye SQ-16 was found to exhibit the decreased photon harvesting, which was explained by the enhanced dye aggregation along with its difficulty in facile electron injection as indicated from electronic absorption spectroscopic and DFT calculation results, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.036