3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6-carboxaldehyde | 914457-47-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6-carboxaldehyde
• 英文别名: 3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6-carbaldehyde；3,4-(2,2-dihexylpropylenedioxy)thiophene-2-carbaldehyde
• CAS: 914457-47-9
• 化学式: C₂₀H₃₂O₃S
• 分子量: 352.538
• InChiKey: JWYCZQVEKQMJJA-UHFFFAOYSA-N

物化性质

• 沸点：
  456.0±33.0 °C(predicted)
• 密度：
  1.028±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6-carboxaldehyde 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,3-bis(8-bromo-3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-6-yl)acrylonitrile
  参考文献：
  名称：

  Soluble Narrow Band Gap and Blue Propylenedioxythiophene-Cyanovinylene Polymers as Multifunctional Materials for Photovoltaic and Electrochromic Applications

  摘要：

  A family of soluble narrow band gap donor- acceptor conjugated polymers based on dioxythiophenes and cyanovinylenes is reported. The polymers were synthesized using Knoevenagel polycondensation or Yamamoto coupling polymerizations to yield polymers with molecular weights on the order of 10000-20000 g/mol, which possess solubility in common organic solvents. Thin film optical measurements revealed narrow band gaps of 1.5-1.8 eV, which gives the polymers a strong overlap of the solar spectrum. The energetic positions of the band edges were determined by cyclic voltammetry and differential pulse voltammetry and demonstrate that the polymers are both air stable and show a strong propensity for photoinduced charge transfer to fullerene acceptors. Such measurements also suggest that the polymers can be both p- and n-type doped, which is supported by spectroelectrochemical results. These polymers have been investigated as electron donors in photovoltaic devices in combination with PCBM ([6,6]-phenyl C-61-butyric acid methyl ester) as an electron acceptor based on the near ideal band structures designed into the polymers. Efficiencies as high as 0.2% (AM1.5) with short circuit current densities as high as 1.2-1.3 mA/cm(2) have been observed in polymer/PCBM (1: 4 by weight) devices and external quantum efficiencies of more than 10% have been observed at wavelengths longer than 600 nm. The electrochromic properties of the narrow band gap polymers are also of interest as the polymers show three accessible color states changing from an absorptive blue or purple in the neutral state to a transmissive sky-blue or gray in the oxidized and reduced forms. The wide electrochemical range of electrochromic activity coupled with the strong observed changes in transmissivity between oxidation states makes these materials potentially interesting for application to electrochromic displays.

  DOI：

  10.1021/ja061274a
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine 在 三氯氧磷 作用下， 以99%的产率得到3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6-carboxaldehyde
  参考文献：
  名称：

  Triphenylamine-Based Dyes Bearing Functionalized 3,4-Propylenedioxythiophene Linkers with Enhanced Performance for Dye-Sensitized Solar Cells

  摘要：

  Introduction of modified 3,4-propylenedioxythiophene units into triphenylamine-based dyes is found to enhance light capturing, suppress dye aggregation, and remarkably retard charge recombination in dye-sensitized solar cells. Open circuit voltages of the as-synthesized dyes (similar to 800 mV) are much higher than that with a thiophene congener (720 mV) under similar conditions as a result of self-passivation benefiting from their three-dimensional branched structures.

  DOI：

  10.1021/ol902973r

文献信息

• Pyridine−EDOT Heteroarylene−Vinylene Donor−Acceptor Polymers
  作者：Alessandro Abbotto、Erika Herrera Calderon、Milind S. Dangate、Filippo De Angelis、Norberto Manfredi、Claudio Maria Mari、Chiara Marinzi、Edoardo Mosconi、Michele Muccini、Riccardo Ruffo、Mirko Seri

  DOI：10.1021/ma1017132

  日期：2010.12.14

  Two heteroarylene-vinylene donor acceptor polymers, P(2,6-Py-V-EDOT) and P(2,5-Py-V-EDOT), containing vinylene-spaced simple donor (EDOT) and acceptor (pyridine) moieties, are presented. The central pyridine ring of the repeating unit is either 2,6- or 2,5-substituted, leading to different structural and electronic properties of the monomers. Polymers were obtained by either oxidative electropolymerization or Yamamoto coupling and fully characterized by NMR, UV-vis absorption, GPC, TGA, DSC, electrochemistry, and spectroelectrochemistry. Detailed ab initio computations have been performed for the monomers and model oligomers for analyzing their optical and electronic properties. GPC showed that isolated polymers obtained via Yamamoto poly coupling have low molecular weights, likely due to solubility issues. The electrochemical polymerizations led to p- and n-dopable polymers, with 2,5-Py-V-EDOT yielding more reversible n-doped process. The energetic positions revealed HOMO (-5.1 and -5.0 eV), LUMO (-3.4 eV), and narrow bandgap (1.6 and 1.7 eV) energies closely matching materials-design rules for optimized organic photovoltaic devices. Preliminary investigation in photovoltaic devices in combination with C-71-PCBM afforded relatively modest power conversion efficiencies of similar to 0.5% (AM 1.5G, 100 mW/cm(2)), which were attributed to the low molecular-weight of the polymers accessible via the chemical route.