N-(3,5-bismethoxycarbonylphenyl)-4-picolinium chloride | 1335151-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(3,5-bismethoxycarbonylphenyl)-4-picolinium chloride
• 英文别名: [(3,5-MC2Ph)pic(1+)]Cl
• CAS: 1335151-62-6
• 化学式: C₁₆H₁₆NO₄*Cl
• 分子量: 321.76
• InChiKey: LRDKZLYUVYSSJB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.15
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.48
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(3,5-bismethoxycarbonylphenyl)-4-picolinium chloride 在 哌啶 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 11.0h， 生成 (E)-4'-(dimethylamino)-N-(3,5-biscarboxyphenyl)-4-stilbazolium hexafluorophosphate
  参考文献：
  名称：

  N-Aryl stilbazolium dyes as sensitizers for solar cells

  摘要：

  Eight new N-arylstilbazolium chromophores with electron donating -NR2 (R = Me or Ph) substituents have been synthesized via Knoevenagel condensations and isolated as their PF6- salts. These compounds have been characterized by using various techniques including H-1 NMR and IR spectroscopies and electrospray mass spectrometry. UV-vis absorption spectra recorded in acetonitrile are dominated by intense, low energy pi -> pi* intramolecular charge-transfer (ICT) bands, and replacing Me with Ph increases the ICT energies. Cyclic voltammetric studies show irreversible reduction processes, together with oxidation waves that are irreversible for R = Me, but reversible for R = Ph. Single crystal X-ray structures have been determined for three of the methyl ester-substituted stilbazolium salts and for the Cl- salts of their picolinium precursors. Time-dependent density functional theory calculations afford reasonable predictions of ICT energies, but greater rigour is necessary for -NPh2 derivatives. The four new acid-functionalized dyes give moderate sensitization efficiencies (ca. 0.2%) when using TiO2-based photoanodes, with relatively higher values for R = Ph vs Me, while larger efficiencies (up to 0.8%) are achieved with ZnO substrates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.06.017
• 作为产物：
  描述：

  4-甲基吡啶 以 乙醇 、 异丙醇 为溶剂， 反应 74.0h， 生成 N-(3,5-bismethoxycarbonylphenyl)-4-picolinium chloride
  参考文献：
  名称：

  N-Aryl stilbazolium dyes as sensitizers for solar cells

  摘要：

  Eight new N-arylstilbazolium chromophores with electron donating -NR2 (R = Me or Ph) substituents have been synthesized via Knoevenagel condensations and isolated as their PF6- salts. These compounds have been characterized by using various techniques including H-1 NMR and IR spectroscopies and electrospray mass spectrometry. UV-vis absorption spectra recorded in acetonitrile are dominated by intense, low energy pi -> pi* intramolecular charge-transfer (ICT) bands, and replacing Me with Ph increases the ICT energies. Cyclic voltammetric studies show irreversible reduction processes, together with oxidation waves that are irreversible for R = Me, but reversible for R = Ph. Single crystal X-ray structures have been determined for three of the methyl ester-substituted stilbazolium salts and for the Cl- salts of their picolinium precursors. Time-dependent density functional theory calculations afford reasonable predictions of ICT energies, but greater rigour is necessary for -NPh2 derivatives. The four new acid-functionalized dyes give moderate sensitization efficiencies (ca. 0.2%) when using TiO2-based photoanodes, with relatively higher values for R = Ph vs Me, while larger efficiencies (up to 0.8%) are achieved with ZnO substrates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.06.017