1,4-bis(4-formyl-2,5-dioctyloxyphenylethynyl)-2,5-dioctyloxybenzene | 431898-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis(4-formyl-2,5-dioctyloxyphenylethynyl)-2,5-dioctyloxybenzene
• 英文别名: 4-[2-[4-[2-(4-Formyl-2,5-dioctoxyphenyl)ethynyl]-2,5-dioctoxyphenyl]ethynyl]-2,5-dioctoxybenzaldehyde；4-[2-[4-[2-(4-formyl-2,5-dioctoxyphenyl)ethynyl]-2,5-dioctoxyphenyl]ethynyl]-2,5-dioctoxybenzaldehyde
• CAS: 431898-27-0
• 化学式: C₇₂H₁₁₀O₈
• 分子量: 1103.66
• InChiKey: SUQXPVGJXDJFJN-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  1031.6±65.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  25.2
• 重原子数：
  80
• 可旋转键数：
  54
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,4-二溴-2,5-二(辛基氧基)苯 在 四(三苯基膦)钯 copper(l) iodide 、 正丁基锂 、 二异丙胺 作用下， 以 乙醚 、 正庚烷 、 甲苯 为溶剂， 反应 25.5h， 生成 1,4-bis(4-formyl-2,5-dioctyloxyphenylethynyl)-2,5-dioctyloxybenzene
  参考文献：
  名称：

  Investigation of the Photophysical and Electrochemical Properties of Alkoxy-Substituted Arylene−Ethynylene/Arylene−Vinylene Hybrid Polymers

  摘要：

  High-molecular-weight, soluble and thermostable alkoxy-substituted arylene-ethynylene/ arylene-vinylene conjugated polymers, 13 and 14, have been successfully synthesized through the Horner-Wadsworth-Emmons olefination of luminophoric dialdehydes 7 and 9 and bisphosphonate 12 in very good yields. They were characterized through H-1 NMR, C-13 NMR, IR, and elemental analysis. The investigation of their photophysical and electrochemical properties has been carried out. Although almost identical absorption and emission spectra were obtained in dilute chloroform solution for all polymers 13, the full width at half-maximum (fwhm) value of the emission curves depends on the length of the attached side chains. The presence of anthracenylene units in 14 leads to a red shift of its absorption and emission spectra relative to 13. Strong self-reabsorption after excitation in solution was observed for this polymer. The solid-state photophysical properties of 13 and 14 (photoconductivity, absorption and emission spectra, fluorescence quantum yield, Stokes shift, and fwhm) greatly depend on the nature (linear or branched), length, and location of the grafted alkoxy side groups. Photoconductivity is easily detected in polymers having octadecyloxy chains (13aa, 13ab, 14). Long linear (octadecyl, i.e., 13aa) or short branched (2-ethylhexyl, i.e., 13cc) side chains at position R-2 (phenylene-vinylene segment) are necessary to obtain sharp and well-resolved emission spectra accompanied by high fluorescence quantum yields. The quasi-donor (phenylene-vinylene segment)-acceptor (arylene-ethynylene segment) nature of these polymers could explain the great discrepancy between the electrochemical band gap energy, E-g(ec) approximate to 1.60 eV, as obtained from the onset values of the redox potentials in cyclic voltammetry and in differential pulse polarography measurements, and the optical band gap energy, E-g(opt) approximate to 2.30 eV, from the absorption spectra.

  DOI：

  10.1021/ma0301395

文献信息

• Investigation of the Photophysical and Electrochemical Properties of Alkoxy-Substituted Arylene−Ethynylene/Arylene−Vinylene Hybrid Polymers
  作者：Daniel Ayuk Mbi Egbe、Bader Cornelia、Jürgen Nowotny、Wolfgang Günther、Elisabeth Klemm

  DOI：10.1021/ma0301395

  日期：2003.7.1

  High-molecular-weight, soluble and thermostable alkoxy-substituted arylene-ethynylene/ arylene-vinylene conjugated polymers, 13 and 14, have been successfully synthesized through the Horner-Wadsworth-Emmons olefination of luminophoric dialdehydes 7 and 9 and bisphosphonate 12 in very good yields. They were characterized through H-1 NMR, C-13 NMR, IR, and elemental analysis. The investigation of their photophysical and electrochemical properties has been carried out. Although almost identical absorption and emission spectra were obtained in dilute chloroform solution for all polymers 13, the full width at half-maximum (fwhm) value of the emission curves depends on the length of the attached side chains. The presence of anthracenylene units in 14 leads to a red shift of its absorption and emission spectra relative to 13. Strong self-reabsorption after excitation in solution was observed for this polymer. The solid-state photophysical properties of 13 and 14 (photoconductivity, absorption and emission spectra, fluorescence quantum yield, Stokes shift, and fwhm) greatly depend on the nature (linear or branched), length, and location of the grafted alkoxy side groups. Photoconductivity is easily detected in polymers having octadecyloxy chains (13aa, 13ab, 14). Long linear (octadecyl, i.e., 13aa) or short branched (2-ethylhexyl, i.e., 13cc) side chains at position R-2 (phenylene-vinylene segment) are necessary to obtain sharp and well-resolved emission spectra accompanied by high fluorescence quantum yields. The quasi-donor (phenylene-vinylene segment)-acceptor (arylene-ethynylene segment) nature of these polymers could explain the great discrepancy between the electrochemical band gap energy, E-g(ec) approximate to 1.60 eV, as obtained from the onset values of the redox potentials in cyclic voltammetry and in differential pulse polarography measurements, and the optical band gap energy, E-g(opt) approximate to 2.30 eV, from the absorption spectra.