7-(4-hydroxyphenyl)-10-(4-(octyloxy)phenyl)-10H-phenothiazine-3-carbaldehyde | 1417703-10-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7-(4-hydroxyphenyl)-10-(4-(octyloxy)phenyl)-10H-phenothiazine-3-carbaldehyde
• 英文别名: 7-(4-Hydroxyphenyl)-10-(4-octoxyphenyl)phenothiazine-3-carbaldehyde；7-(4-hydroxyphenyl)-10-(4-octoxyphenyl)phenothiazine-3-carbaldehyde
• CAS: 1417703-10-6
• 化学式: C₃₃H₃₃NO₃S
• 分子量: 523.696
• InChiKey: YBEYIEOXRBSESS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-溴辛烷 、 7-(4-hydroxyphenyl)-10-(4-(octyloxy)phenyl)-10H-phenothiazine-3-carbaldehyde 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以91%的产率得到7,10-bis(4-(octyloxy)phenyl)-10H-phenothiazine-3-carbaldehyde
  参考文献：
  名称：

  Phenothiazine-based dyes with bilateral extension of π-conjugation for efficient dye-sensitized solar cells

  摘要：

  Four novel organic photo-sensitizers based on phenothiazine were designed, synthesized and characterized for efficient dye-sensitized solar cells. Anisole, octyloxybenzene and dodecyloxybenzene were incorporated into the phenothiazine by an Ullmann reaction. An additional octyloxybenzene was incorporated into one dye unit through a Suzuki coupling reaction. The modified phenothiazine moiety acts as an electron donor and cyanoacrylic acid acts as an electron acceptor and anchoring unit. The photophysical, electrochemical and sensitizing characteristics of the new dyes were evaluated. The bis(octyloxybenzene) substituted dye delivered the best performance with its sensitized solar cell displaying an overall power conversion efficiency of 5.73% under standard illumination. The results indicate that bilateral conjugate extension of the pi conjugation can increase their light harvesting capacity and electron lifetime, leading to improvements in the efficiency of their dye-sensitized solar cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.11.010
• 作为产物：
  描述：

  10-(4-octyloxyphenyl)-10H-phenothiazine-3-carbaldehyde 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 56.5h， 生成 7-(4-hydroxyphenyl)-10-(4-(octyloxy)phenyl)-10H-phenothiazine-3-carbaldehyde
  参考文献：
  名称：

  Phenothiazine-based dyes with bilateral extension of π-conjugation for efficient dye-sensitized solar cells

  摘要：

  Four novel organic photo-sensitizers based on phenothiazine were designed, synthesized and characterized for efficient dye-sensitized solar cells. Anisole, octyloxybenzene and dodecyloxybenzene were incorporated into the phenothiazine by an Ullmann reaction. An additional octyloxybenzene was incorporated into one dye unit through a Suzuki coupling reaction. The modified phenothiazine moiety acts as an electron donor and cyanoacrylic acid acts as an electron acceptor and anchoring unit. The photophysical, electrochemical and sensitizing characteristics of the new dyes were evaluated. The bis(octyloxybenzene) substituted dye delivered the best performance with its sensitized solar cell displaying an overall power conversion efficiency of 5.73% under standard illumination. The results indicate that bilateral conjugate extension of the pi conjugation can increase their light harvesting capacity and electron lifetime, leading to improvements in the efficiency of their dye-sensitized solar cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.11.010

文献信息

• Phenothiazine-based dyes with bilateral extension of π-conjugation for efficient dye-sensitized solar cells
  作者：Zafar Iqbal、Wu-Qiang Wu、Dai-Bin Kuang、Lingyun Wang、Herbert Meier、Derong Cao

  DOI：10.1016/j.dyepig.2012.11.010

  日期：2013.3

  Four novel organic photo-sensitizers based on phenothiazine were designed, synthesized and characterized for efficient dye-sensitized solar cells. Anisole, octyloxybenzene and dodecyloxybenzene were incorporated into the phenothiazine by an Ullmann reaction. An additional octyloxybenzene was incorporated into one dye unit through a Suzuki coupling reaction. The modified phenothiazine moiety acts as an electron donor and cyanoacrylic acid acts as an electron acceptor and anchoring unit. The photophysical, electrochemical and sensitizing characteristics of the new dyes were evaluated. The bis(octyloxybenzene) substituted dye delivered the best performance with its sensitized solar cell displaying an overall power conversion efficiency of 5.73% under standard illumination. The results indicate that bilateral conjugate extension of the pi conjugation can increase their light harvesting capacity and electron lifetime, leading to improvements in the efficiency of their dye-sensitized solar cells. (C) 2012 Elsevier Ltd. All rights reserved.