3,4-dimethoxythiophene-2-carbaldehyde | 51792-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dimethoxythiophene-2-carbaldehyde
• 英文别名: 3,4-dimethoxy-thiophene-2-carbaldehyde；3,4-Dimethoxythiophen-2-carbaldehyd；3,4-Dimethoxythiophene-2-carbaldehyde
• CAS: 51792-38-2
• 化学式: C₇H₈O₃S
• 分子量: 172.205
• InChiKey: FUJWFUQYKOKBBW-UHFFFAOYSA-N

物化性质

• 沸点：
  287.6±35.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxythiophene-2-carbaldehyde 在 哌啶 、 sodium acetate 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 52.5h， 生成 5-(2-cyanoacrylic acid-3-yl)-3,4-dimethyloxythiophene-2-carbaldehyde-N,N-diphenylhydrazone
  参考文献：
  名称：

  Synthesis of new N, N-diphenylhydrazone dyes for solar cells: Effects of thiophene-derived π-conjugated bridge

  摘要：

  Four novel D-pi-A hydrazone dyes (HT, HM, HE, and HO) with an N, N-diphenylhydrazone moiety as the electron donor, different thiophene-derived pi-conjugated bridges and a cyanoacrylic acid moiety as the electron acceptor have been designed and synthesized for the application in dye-sensitized solar cells. The influences of thiophene-derived bridges on the photoelectrochemical and photovoltaic performance of these hydrazone dyes were investigated. Results demonstrate that the introduction of 3,4-dialkyloxythiophene could red-shift the dye's absorption spectrum due to the enhancement of the electron-donating ability of pi-conjugated bridges. Importantly, electrochemical impedance spectroscopy analysis reveal that 3,4-dialkyloxythiophene bridge could change the charge recombination resistance at the TiO2/dye/electrolyte interface and as a result to improve the open-circuit photovoltage. Among the four dyes, HO exhibits the maximum power conversion efficiency of 5.83% (V-oc = 0.65 V, J(sc) = 12.69 mA/cm(2), FF = 0.707) under simulated AM 1.5 irradiation (100 mW/cm(2)). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.08.014
• 作为产物：
  描述：

  3,4-二甲氧基噻吩 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 4.5h， 以63%的产率得到3,4-dimethoxythiophene-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of new N, N-diphenylhydrazone dyes for solar cells: Effects of thiophene-derived π-conjugated bridge

  摘要：

  Four novel D-pi-A hydrazone dyes (HT, HM, HE, and HO) with an N, N-diphenylhydrazone moiety as the electron donor, different thiophene-derived pi-conjugated bridges and a cyanoacrylic acid moiety as the electron acceptor have been designed and synthesized for the application in dye-sensitized solar cells. The influences of thiophene-derived bridges on the photoelectrochemical and photovoltaic performance of these hydrazone dyes were investigated. Results demonstrate that the introduction of 3,4-dialkyloxythiophene could red-shift the dye's absorption spectrum due to the enhancement of the electron-donating ability of pi-conjugated bridges. Importantly, electrochemical impedance spectroscopy analysis reveal that 3,4-dialkyloxythiophene bridge could change the charge recombination resistance at the TiO2/dye/electrolyte interface and as a result to improve the open-circuit photovoltage. Among the four dyes, HO exhibits the maximum power conversion efficiency of 5.83% (V-oc = 0.65 V, J(sc) = 12.69 mA/cm(2), FF = 0.707) under simulated AM 1.5 irradiation (100 mW/cm(2)). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.08.014

文献信息

• Synthesis of new N, N-diphenylhydrazone dyes for solar cells: Effects of thiophene-derived π-conjugated bridge
  作者：Ping Shen、Xinping Liu、Shenghui Jiang、Ling Wang、Ling Yi、Dandan Ye、Bin Zhao、Songting Tan

  DOI：10.1016/j.dyepig.2011.08.014

  日期：2012.3

  Four novel D-pi-A hydrazone dyes (HT, HM, HE, and HO) with an N, N-diphenylhydrazone moiety as the electron donor, different thiophene-derived pi-conjugated bridges and a cyanoacrylic acid moiety as the electron acceptor have been designed and synthesized for the application in dye-sensitized solar cells. The influences of thiophene-derived bridges on the photoelectrochemical and photovoltaic performance of these hydrazone dyes were investigated. Results demonstrate that the introduction of 3,4-dialkyloxythiophene could red-shift the dye's absorption spectrum due to the enhancement of the electron-donating ability of pi-conjugated bridges. Importantly, electrochemical impedance spectroscopy analysis reveal that 3,4-dialkyloxythiophene bridge could change the charge recombination resistance at the TiO2/dye/electrolyte interface and as a result to improve the open-circuit photovoltage. Among the four dyes, HO exhibits the maximum power conversion efficiency of 5.83% (V-oc = 0.65 V, J(sc) = 12.69 mA/cm(2), FF = 0.707) under simulated AM 1.5 irradiation (100 mW/cm(2)). (C) 2011 Elsevier Ltd. All rights reserved.