triethylammonium 2-butoxy-3-(dicyanomethylene)-4-oxocyclobut-1-enolate | 848485-56-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: triethylammonium 2-butoxy-3-(dicyanomethylene)-4-oxocyclobut-1-enolate
• 英文别名: N,N-diethylethanamine;2-[3-hydroxy-2-[(2-methylpropan-2-yl)oxy]-4-oxocyclobut-2-en-1-ylidene]propanedinitrile
• CAS: 848485-56-3
• 化学式: C₆H₁₅N*C₁₁H₁₀N₂O₃
• 分子量: 319.404
• InChiKey: FKNBUPIZEJSWFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  97.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  triethylammonium 2-butoxy-3-(dicyanomethylene)-4-oxocyclobut-1-enolate 、 5-bromo-1-(3,7-dimethyloctyl)-2,3,3-trimethyl-3H-indol-1-ium tosylate 在 吡啶 作用下， 以 甲苯 、 正丁醇 为溶剂， 反应 17.0h， 以82%的产率得到[2-[4-[[5-Bromo-1-(3,7-dimethyloctyl)-3,3-dimethylindol-1-ium-2-yl]methylidene]-2-[[5-bromo-1-(3,7-dimethyloctyl)-3,3-dimethylindol-2-ylidene]methyl]-3-oxocyclobuten-1-yl]-2-cyanoethenylidene]azanide
  参考文献：
  名称：

  Exciton Coupling Effects in Polymeric cis-Indolenine Squaraine Dyes

  摘要：

  Dicyanovinylene-substituted cis-indolenine squaraines were polymerized by a Ni-mediated Yamamoto homocoupling reaction. Preparative recycling GPC was used to obtain polymer fractions with different molecular weight distributions in order to investigate the influence of molecular weight on the optical properties. In this attempt, conjugated cyclic trimers could also be isolated that are, to the best of our knowledge, the first of their kind. These trimers and the squaraine polymers were investigated by cyclic voltammetry, absorption spectroscopy, and static and time-resolved fluorescence spectroscopy. While the trimers show multiple fluorescence bands with, for squaraines, an exceptional huge Stokes' shift, the polymers show broad absorption in the red to near infrared (NIR) region with narrow fluorescence and only the common minor Stokes' shift. The spectral features of the squaraines were interpreted to be caused by excitonic coupling. By comparison of experimental and computed (CNDO/S2 CIS) spectra detailed, structural models of the polymers were derived that consist of helix (H-aggregate behavior) and zigzag motifs (J-aggregate behavior).

  DOI：

  10.1021/cm301109u

文献信息

• Exciton Coupling Effects in Polymeric <i>cis</i>-Indolenine Squaraine Dyes
  作者：Sebastian F. Völker、Christoph Lambert

  DOI：10.1021/cm301109u

  日期：2012.7.10

  Dicyanovinylene-substituted cis-indolenine squaraines were polymerized by a Ni-mediated Yamamoto homocoupling reaction. Preparative recycling GPC was used to obtain polymer fractions with different molecular weight distributions in order to investigate the influence of molecular weight on the optical properties. In this attempt, conjugated cyclic trimers could also be isolated that are, to the best of our knowledge, the first of their kind. These trimers and the squaraine polymers were investigated by cyclic voltammetry, absorption spectroscopy, and static and time-resolved fluorescence spectroscopy. While the trimers show multiple fluorescence bands with, for squaraines, an exceptional huge Stokes' shift, the polymers show broad absorption in the red to near infrared (NIR) region with narrow fluorescence and only the common minor Stokes' shift. The spectral features of the squaraines were interpreted to be caused by excitonic coupling. By comparison of experimental and computed (CNDO/S2 CIS) spectra detailed, structural models of the polymers were derived that consist of helix (H-aggregate behavior) and zigzag motifs (J-aggregate behavior).