5-{2-[7-(diphenylamino)-9,9-diethyl-9H-fluoren-2-yl]ethynyl}thiophene-2-carbaldehyde | 1401100-10-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-{2-[7-(diphenylamino)-9,9-diethyl-9H-fluoren-2-yl]ethynyl}thiophene-2-carbaldehyde
• CAS: 1401100-10-4
• 化学式: C₃₆H₂₉NOS
• 分子量: 523.698
• InChiKey: GFUKKSGMUCPJFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.52
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-{2-[7-(diphenylamino)-9,9-diethyl-9H-fluoren-2-yl]ethynyl}thiophene-2-carbaldehyde 、 氰乙酸 在 乙酸铵 、 溶剂黄146 作用下， 反应 12.0h， 以67%的产率得到(E)-2-cyano-3-(5-(2-(7-(diphenylamino)-9,9-diethyl-9H-fluoren-2-yl)ethynyl)thiophen-2-yl)acrylic acid
  参考文献：
  名称：

  Fluorene-based organic dyes containing acetylene linkage for dye-sensitized solar cells

  摘要：

  New organic dyes based on diphenylaminofluorene donors, cyanoacrylic acid acceptors and either ethynylbenzene or ethynylthiophene pi-spacers have been synthesized and characterized as sensitizers for dye-sensitized solar cells. The dye with thiophene in the conjugation pathway exhibited longer wavelength absorption due to the significant lowering of the LUMO level when compared to the phenyl analog. However, the dye with the phenylacetylene linker displayed promising DSSC characteristics such as short circuit current, open circuit voltage and fill factor indicative of efficient charge generation and injection. The solvatochromic behavior of the dyes were examined in solvents of different polarity and found to exhibit negative solvatochromism of the fluorescence emission suggestive of a nonpolar solvent stabilized excited state with a significant structural reorganization. The TDDFT computations were used to explain the optical properties of the dyes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.06.004
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 9,9-diethyl-7-ethynyl-N,N-diphenyl-9H-fluoren-2-amine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 反应 24.0h， 以75%的产率得到5-{2-[7-(diphenylamino)-9,9-diethyl-9H-fluoren-2-yl]ethynyl}thiophene-2-carbaldehyde
  参考文献：
  名称：

  Fluorene-based organic dyes containing acetylene linkage for dye-sensitized solar cells

  摘要：

  New organic dyes based on diphenylaminofluorene donors, cyanoacrylic acid acceptors and either ethynylbenzene or ethynylthiophene pi-spacers have been synthesized and characterized as sensitizers for dye-sensitized solar cells. The dye with thiophene in the conjugation pathway exhibited longer wavelength absorption due to the significant lowering of the LUMO level when compared to the phenyl analog. However, the dye with the phenylacetylene linker displayed promising DSSC characteristics such as short circuit current, open circuit voltage and fill factor indicative of efficient charge generation and injection. The solvatochromic behavior of the dyes were examined in solvents of different polarity and found to exhibit negative solvatochromism of the fluorescence emission suggestive of a nonpolar solvent stabilized excited state with a significant structural reorganization. The TDDFT computations were used to explain the optical properties of the dyes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.06.004