2,6-Bis(dihexylamino)-4,8-dipyridin-4-ylfuro[2,3-f][1]benzofuran-3,7-dicarbonitrile | 1227073-86-0

• 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: 2,6-Bis(dihexylamino)-4,8-dipyridin-4-ylfuro[2,3-f][1]benzofuran-3,7-dicarbonitrile
• CAS: 1227073-86-0
• 化学式: C₄₆H₆₀N₆O₂
• 分子量: 729.021
• InChiKey: QSQCZLNSMQTEOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  54
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-Bis(dihexylamino)-4,8-dipyridin-4-ylfuro[2,3-f][1]benzofuran-3,7-dicarbonitrile 、 碘甲烷 在 六氟磷酸钾 作用下， 以 乙腈 、 水 为溶剂， 反应 0.5h， 以65%的产率得到
  参考文献：
  名称：

  Versatile Strategy To Access Fully Functionalized Benzodifurans: Redox-Active Chromophores for the Construction of Extended π-Conjugated Materials

  摘要：

  An efficient synthetic approach to construct a fully substituted benzo[1,2-b:4,5-b']difuran (BDF) 2a via base-catalyzed double annulations is presented. Compound 2a can readily undergo Suzuki, Heck, and Sonogashira coupling reactions to afford in good yields a manifold of extended pi-conjugated BDF derivatives, e.g., with pyridine termini (4-6) and with different spacers. These are highly luminescent materials that undergo two reversible one-electron oxidations. Remarkably, their photophysical and electrochemical properties can be largely tuned by methylation or protonation. Consequently, they can function as pH-dependent fluorescence switches. Finally, the observed electronic properties are explained on the basis of density functional theory.

  DOI：

  10.1021/jo100323s
• 作为产物：
  描述：

  2,6-bis(N,N-dihexylamino)-4,8-diiodobenzo[1,2-b:4,5-b’]difuran-3,7-dicarbonitrile 、 吡啶-4-硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以85%的产率得到2,6-Bis(dihexylamino)-4,8-dipyridin-4-ylfuro[2,3-f][1]benzofuran-3,7-dicarbonitrile
  参考文献：
  名称：

  Versatile Strategy To Access Fully Functionalized Benzodifurans: Redox-Active Chromophores for the Construction of Extended π-Conjugated Materials

  摘要：

  An efficient synthetic approach to construct a fully substituted benzo[1,2-b:4,5-b']difuran (BDF) 2a via base-catalyzed double annulations is presented. Compound 2a can readily undergo Suzuki, Heck, and Sonogashira coupling reactions to afford in good yields a manifold of extended pi-conjugated BDF derivatives, e.g., with pyridine termini (4-6) and with different spacers. These are highly luminescent materials that undergo two reversible one-electron oxidations. Remarkably, their photophysical and electrochemical properties can be largely tuned by methylation or protonation. Consequently, they can function as pH-dependent fluorescence switches. Finally, the observed electronic properties are explained on the basis of density functional theory.

  DOI：

  10.1021/jo100323s