4-nitro-4'-carboxy-α-cyanostilbene | 571938-92-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-nitro-4'-carboxy-α-cyanostilbene
• 英文别名: 4-[2-Cyano-2-(4-nitrophenyl)ethenyl]benzoic acid
• CAS: 571938-92-6
• 化学式: C₁₆H₁₀N₂O₄
• 分子量: 294.266
• InChiKey: MNWMWZCCXWDTNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯乙腈 在 硫酸 、 硝酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-nitro-4'-carboxy-α-cyanostilbene
  参考文献：
  名称：

  Simple sensitizers of low band gap based on 4-nitro-α-cyanostilbene prepared from a one-step reaction for efficient dye-sensitized solar cells

  摘要：

  Two simple dyes D1 and D2 based on 4-nitro-alpha-cyanostilbene were conveniently synthesized from a one-step reaction. These dyes were prepared from the condensation of 4-carboxybenzaldehyde or 4-hydroxybenzaldehyde with 4-nitrobenzyl cyanide to afford 4-nitro-4'-carboxy-alpha-cyanostilbene (D1) and 4-nitro-4'-hydroxy-alpha-cyanostilbene (D2) respectively. Photophysical and electrochemical properties of the dyes were investigated by UV-vis spectroscopy and cyclic voltammetry. Their absorption spectra were broad with long-wavelength absorption maximum at 617-655 nm and optical band gap of 1.63 eV. These two dyes were used as sensitizers in quasi solid state dye-sensitized solar cells (DSSCs). Photovoltaic devices with D1 showed a maximum monochromatic incident photon to current efficiency (IPCE) of 70% and overall power conversion efficiency (PCE) of 4.8%, under illumination intensity 100 mW/cm(2). The photovoltaic performance of the cell with D-2 was lower because of less dye loading on the TiO2 surface, since it has OH anchoring group, and lower electron lifetime. Additionally, we have investigated the photovoltaic response of the DSSCs with nitrogen doped TiO2 photoanode and found that the PCE has been enhanced. The enhancement in PCE has been attributed to the increase in open circuit voltage and fill factor. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.05.002

文献信息

• Simple sensitizers of low band gap based on 4-nitro-α-cyanostilbene prepared from a one-step reaction for efficient dye-sensitized solar cells
  作者：J.A. Mikroyannidis、D.V. Tsagkournos、P. Balraju、G.D. Sharma

  DOI：10.1016/j.orgel.2010.05.002

  日期：2010.7

  Two simple dyes D1 and D2 based on 4-nitro-alpha-cyanostilbene were conveniently synthesized from a one-step reaction. These dyes were prepared from the condensation of 4-carboxybenzaldehyde or 4-hydroxybenzaldehyde with 4-nitrobenzyl cyanide to afford 4-nitro-4'-carboxy-alpha-cyanostilbene (D1) and 4-nitro-4'-hydroxy-alpha-cyanostilbene (D2) respectively. Photophysical and electrochemical properties of the dyes were investigated by UV-vis spectroscopy and cyclic voltammetry. Their absorption spectra were broad with long-wavelength absorption maximum at 617-655 nm and optical band gap of 1.63 eV. These two dyes were used as sensitizers in quasi solid state dye-sensitized solar cells (DSSCs). Photovoltaic devices with D1 showed a maximum monochromatic incident photon to current efficiency (IPCE) of 70% and overall power conversion efficiency (PCE) of 4.8%, under illumination intensity 100 mW/cm(2). The photovoltaic performance of the cell with D-2 was lower because of less dye loading on the TiO2 surface, since it has OH anchoring group, and lower electron lifetime. Additionally, we have investigated the photovoltaic response of the DSSCs with nitrogen doped TiO2 photoanode and found that the PCE has been enhanced. The enhancement in PCE has been attributed to the increase in open circuit voltage and fill factor. (c) 2010 Elsevier B.V. All rights reserved.