10-(4-octyloxyphenyl)-10H-phenothiazine | 1189130-48-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 10-(4-octyloxyphenyl)-10H-phenothiazine
• 英文别名: 10-(4-Octoxyphenyl)phenothiazine；10-(4-octoxyphenyl)phenothiazine
• CAS: 1189130-48-0
• 化学式: C₂₆H₂₉NOS
• 分子量: 403.588
• InChiKey: VOSJNVHAEMYKHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-(4-octyloxyphenyl)-10H-phenothiazine 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 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：

  吩噻嗪 、 4-(n-octyloxy)-iodobenzene 在 18-冠醚-6 、 铜 、 potassium carbonate 作用下， 以 邻二氯苯 为溶剂， 反应 48.0h， 以54%的产率得到10-(4-octyloxyphenyl)-10H-phenothiazine
  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

• Synthesis and characterization of fluorene‐based oligomers and polymers incorporating <i>N</i> ‐arylphenothiazine‐ <i>S,S</i> ‐dioxide units
  作者：Kiran T. Kamtekar、Katja Dahms、Andrei S. Batsanov、Vygintas Jankus、Helen L. Vaughan、Andrew P. Monkman、Martin R. Bryce

  DOI：10.1002/pola.24527

  日期：2011.3

  A series of 3,7‐bis(9,9‐di‐n‐hexylfluoren‐2‐yl)‐N‐arylphenothiazine‐S,S‐dioxide trimers and (9,9‐di‐n‐octylfluorene‐2,7‐diyl‐co‐N‐arylphenothiazine‐S,S‐dioxide) co‐polymers, with varying ratios of phenothiazine‐S,S‐dioxide units, have been prepared in good yields by palladium‐catalyzed cross‐coupling reactions. The materials are deep blue emitters and show no solvatochromism or evidence for an intramolecular

  一系列3,7-双（9,9-二-n-己基芴-2-基）-N-芳基吩噻嗪-S，S-二氧化物三聚体和（9,9-二-n-辛基芴-2,7-二基-共- ñ -arylphenothiazine- S，S二氧化物）共聚物，与吩噻嗪的不同比率S，S二氧化物单元，已在良好的产率通过钯催化的交叉偶联反应来制备。这些材料是深蓝色发射体，没有溶剂溶变色现象或分子内电荷转移状态的证据。三聚体的光致发光量子产率在溶液中为ϕ PL的15–30％，在薄膜中为14–25％。聚合物在溶液中显示出很高的值（ϕ PL 74–84％），并且ϕ胶卷中的PL值为28–47％。对于结合了吩噻嗪-S，S-二氧化物单元的15％的聚合物，估计的HOMO能级在-5.64至-5.62 eV之间。类似的N-芳基吩噻嗪共聚物显示出明显的红移吸收和发射。还介绍了溶液电化学数据和密度泛函理论计算。©2010 Wiley Periodicals，Inc. J
• Trilateral π-conjugation extensions of phenothiazine-based dyes enhance the photovoltaic performance of the dye-sensitized solar cells
  作者：Zafar Iqbal、Wu-Qiang Wu、Zu-Sheng Huang、Lingyun Wang、Dai-Bin Kuang、Herbert Meier、Derong Cao

  DOI：10.1016/j.dyepig.2015.09.001

  日期：2016.1

  Two novel organic dyes TLEP-1 and TLEP-2 based on phenothiazine with trilateral pi-conjugation extensions were designed and synthesized for dye-sensitized solar cells, where phenothiazine ring was linked with two phenyl moieties at 7- and 10-positions as the first and second pi-conjugation extensions, and with furan or thiophene ring at 3-position as the third pi-conjugation extension for TLEP-1 and TLEP-2, respectively. The influence of the pi-conjugation extensions on the photovoltaic performance was evaluated. The cell based on TLEP-2 exhibits an impressive short-circuit photocurrent density of 14.87 mA cm(-2), which is much higher than the cell based on the reference dye without pi-conjugation extension (9.01 mA cm(-2)), leading to high power conversion efficiency of 7.33% under simulated AM 1.5 G illumination condition. The results indicate that the trilateral pi-conjugation extensions are an effective way to improve the photovoltaic performance of the dye-sensitized solar cells. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.