5-(3-(4-(diphenylamino)phenyl)-9-ethylcarbazole-6-yl)-3-hexylthiophene-2-carbaldehyde | 1245644-28-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(3-(4-(diphenylamino)phenyl)-9-ethylcarbazole-6-yl)-3-hexylthiophene-2-carbaldehyde
• 英文别名: 5-[9-ethyl-6-[4-(N-phenylanilino)phenyl]carbazol-3-yl]-3-hexylthiophene-2-carbaldehyde
• CAS: 1245644-28-3
• 化学式: C₄₃H₄₀N₂OS
• 分子量: 632.869
• InChiKey: YKYYEJPDPQAQPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-(4-(diphenylamino)phenyl)-9-ethylcarbazole-6-yl)-3-hexylthiophene-2-carbaldehyde 、 氰乙酸 在 哌啶 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 12.0h， 以59%的产率得到3-(5-(3-(4-(diphenylamino)phenyl)-9-ethylcarbazole-6-yl)-3-hexylthiophene-2-yl)-2-cyanoacrylic acid
  参考文献：
  名称：

  Efficient triphenylamine-based dyes featuring dual-role carbazole, fluorene and spirobifluorene moieties

  摘要：

  Three triphenylamine-based organic dyes SD6, SD7, and SD8 containing the bulky dual-role moieties (fluorene, carbazole, and spirobifluorene) in the molecular frameworks were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). The effects of dual-role moieties of organic dyes on their photophysical, electrochemical, and photovoltaic properties have been investigated in detail. These dyes exhibit strong charge transfer absorption bands in the visible region. Their redox potential levels were estimated by cyclic voltammetry and found to suit well to the charge flow in DSSCs. Inserting the dual-role moieties as the secondary donor between the triphenylamine and thiophene units increased the electron density of the donor groups, therefore reduced the HOMO-LUMO band gaps. The combination of ultraviolet-visible (UV-vis) region broad absorption bands with fairly high extinction coefficients and appropriate redox properties observed in these triphenylamine-based dyes make them promising dyes for DSSCs. For a typical solar cell device based on dye SD6, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to similar to 73%, with a short-circuit photocurrent density (J(sc)) of 14.25 mA/cm(2), an open-circuit photovoltage (V-oc) of 0.70 V, and a fill factor (FF) of 0.705, which corresponds to a power conversion efficiency (PCE) of 7.03%. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.10.016
• 作为产物：
  描述：

  3,6-二溴-9-乙基咔唑 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 96.5h， 生成 5-(3-(4-(diphenylamino)phenyl)-9-ethylcarbazole-6-yl)-3-hexylthiophene-2-carbaldehyde
  参考文献：
  名称：

  Efficient triphenylamine-based dyes featuring dual-role carbazole, fluorene and spirobifluorene moieties

  摘要：

  Three triphenylamine-based organic dyes SD6, SD7, and SD8 containing the bulky dual-role moieties (fluorene, carbazole, and spirobifluorene) in the molecular frameworks were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). The effects of dual-role moieties of organic dyes on their photophysical, electrochemical, and photovoltaic properties have been investigated in detail. These dyes exhibit strong charge transfer absorption bands in the visible region. Their redox potential levels were estimated by cyclic voltammetry and found to suit well to the charge flow in DSSCs. Inserting the dual-role moieties as the secondary donor between the triphenylamine and thiophene units increased the electron density of the donor groups, therefore reduced the HOMO-LUMO band gaps. The combination of ultraviolet-visible (UV-vis) region broad absorption bands with fairly high extinction coefficients and appropriate redox properties observed in these triphenylamine-based dyes make them promising dyes for DSSCs. For a typical solar cell device based on dye SD6, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to similar to 73%, with a short-circuit photocurrent density (J(sc)) of 14.25 mA/cm(2), an open-circuit photovoltage (V-oc) of 0.70 V, and a fill factor (FF) of 0.705, which corresponds to a power conversion efficiency (PCE) of 7.03%. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.10.016

文献信息

• Efficient triphenylamine-based dyes featuring dual-role carbazole, fluorene and spirobifluorene moieties
  作者：Ping Shen、Yuhua Tang、Shenghui Jiang、Huajie Chen、Xiaoyan Zheng、Xueye Wang、Bin Zhao、Songting Tan

  DOI：10.1016/j.orgel.2010.10.016

  日期：2011.1

  Three triphenylamine-based organic dyes SD6, SD7, and SD8 containing the bulky dual-role moieties (fluorene, carbazole, and spirobifluorene) in the molecular frameworks were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). The effects of dual-role moieties of organic dyes on their photophysical, electrochemical, and photovoltaic properties have been investigated in detail. These dyes exhibit strong charge transfer absorption bands in the visible region. Their redox potential levels were estimated by cyclic voltammetry and found to suit well to the charge flow in DSSCs. Inserting the dual-role moieties as the secondary donor between the triphenylamine and thiophene units increased the electron density of the donor groups, therefore reduced the HOMO-LUMO band gaps. The combination of ultraviolet-visible (UV-vis) region broad absorption bands with fairly high extinction coefficients and appropriate redox properties observed in these triphenylamine-based dyes make them promising dyes for DSSCs. For a typical solar cell device based on dye SD6, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to similar to 73%, with a short-circuit photocurrent density (J(sc)) of 14.25 mA/cm(2), an open-circuit photovoltage (V-oc) of 0.70 V, and a fill factor (FF) of 0.705, which corresponds to a power conversion efficiency (PCE) of 7.03%. (C) 2010 Elsevier B. V. All rights reserved.