3,4-ethylendioxythiophene-2-carbaldehyde-N,N-diphenylhydrazone | 871239-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-ethylendioxythiophene-2-carbaldehyde-N,N-diphenylhydrazone
• 英文别名: 2,3-Dihydrothieno[3,4-b]-1,4-dioxin-5-carboxaldehyde 2,2-diphenylhydrazone；N-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-ylmethylideneamino)-N-phenylaniline
• CAS: 871239-68-8
• 化学式: C₁₉H₁₆N₂O₂S
• 分子量: 336.414
• InChiKey: KSOYZXJQROGITK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.06
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,4-ethylendioxythiophene-2-carbaldehyde-N,N-diphenylhydrazone 在 哌啶 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 28.5h， 生成 5-(2-cyanoacrylic acid-3-yl)-3,4-ethylendioxythiophene-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-乙烯二氧噻吩 在 sodium acetate 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.5h， 生成 3,4-ethylendioxythiophene-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