10-(4-dodecyloxyphenyl)-10H-phenothiazine | 1211331-96-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 10-(4-dodecyloxyphenyl)-10H-phenothiazine
• 英文别名: 10-(4-dodecyloxyphenyl)phenothiazine；10-(4-Dodecoxyphenyl)phenothiazine；10-(4-dodecoxyphenyl)phenothiazine
• CAS: 1211331-96-2
• 化学式: C₃₀H₃₇NOS
• 分子量: 459.696
• InChiKey: CROAHSIVNVSCLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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-dodecyloxyphenyl)-10H-phenothiazine 在 N-溴代丁二酰亚胺(NBS) 、 trans-bis(triphenylphosphine)palladium dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成
  参考文献：
  名称：

  Effect of intermolecular interaction with phenothiazine core on inverted organic photovoltaics by using different acceptor moiety

  摘要：

  Six novel small molecules containing phenothiazine as the core moiety of p-type materials were synthesized in combination with PC61BM or PC71BM as n-type materials for bulk heterojunction organic photovoltaic (OPV) cells. Phenothiazine was used as donor building blocks to construct acceptor donor acceptor (A-D-A) and ADD A small molecule. We investigated the relationship between the molecular structures, optoelectronic and thermal properties, and their blend film morphologies for OPV applications. We further studied their photophysical properties using a time-dependent density functional theory model and the B3LYP functional. A solution-processed OPV employing PT2-DE combined with the electron acceptor PC61BM and additive 010 achieved optimal device performance, with a shortcircuit current 'of 6.3 mASix novel small molecules containing phenothiazine as the core moiety of p -type materials were synthesized in combination with PC6113M or PC71BM as n -type materials for bulk heterojunction organic photovoltaic (OPV) cells. Phenothiazine was used as donor building blocks to construct acceptor donor acceptor (A D A) and A D D A small molecule. We investigated the relationship between the molecular structures, optoelectronic and thermal properties, and their blend film morphologies for OPV applications. We further studied their photophysical properties using a time -dependent density functional theory model and the B3LYP functional. A solution -processed OPV employing PT2-DE combined with the electron acceptor PC61BM and additive 010 achieved optimal device performance, with a shortcircuit current 'of 6.3 mA cm -2, an open -circuit voltage of 770 mV, a fill factor of 0.55, and a corresponding overall conversion efficiency of 2.64%. To the best of our knowledge, this is the best -reported performance of a phenothiazine derivative for OPV application. 2017 Elsevier Ltd. All rights reserved. cm(-2), an open-circuit voltage of 770 mV, a fill factor of 0.55, and a corresponding overall conversion efficiency of 2.64%. To the best of our knowledge, this is the best-reported performance of a phenothiazine derivative for OPV application. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2017.07.027
• 作为产物：
  描述：

  吩噻嗪 、 1-十二烷氧基-4-碘苯 在 18-冠醚-6 、 铜 、 potassium carbonate 作用下， 以 邻二氯苯 为溶剂， 反应 48.0h， 以53%的产率得到10-(4-dodecyloxyphenyl)-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 properties of phenothiazylene vinylene-based polymers: New organic semiconductors for field-effect transistors and solar cells
  作者：Seon-Kyoung Son、Yoon-Suk Choi、Woo-Hyung Lee、Yongtaek Hong、Jae-Ryoung Kim、Won-Suk Shin、Sang-Jin Moon、Do-Hoon Hwang、In-Nam Kang

  DOI：10.1002/pola.23814

  日期：2010.2.1

  features. UV–visible absorption spectra of the polymers showed two strong absorption bands in the ranges 315–370 nm and 450–500 nm, which arose from absorptions of the phenothiazine segments and the conjugated main chains. Solution‐processed field‐effect transistors fabricated from these polymers showed p‐type organic thin‐film transistor characteristics. The field‐effect mobilities of P1, P2, and P3

  一系列新的基于碳酸亚乙烯phenothiazylene半导体聚合物，聚[3,7-（4'-十二烷氧基）phenothiazylene乙炔]（P1），聚[3,7-（4'-十二烷氧基）phenothiazylene vinylene- ALT -1,4-亚苯基乙烯撑]（P2），和聚[3,7-（4'-十二烷氧基）phenothiazylene vinylene- ALT -2,5-亚噻吩基亚乙烯基]（P3），都通过Horner-Emmons反应被合成。FTIR和1个1 H NMR光谱证实，在聚合物中的亚乙烯基的结构是所有-反式（É）。P1的重均分子量（M w），发现P2和P3分别为27,000、22,000和29,000，多分散指数分别为1.91、2.05和2.25。P1，P2和P3的热谱图分别仅包含一个宽的玻璃化转变温度，分别在129、167和155°C，而没有观察到熔融特征。聚合物的紫外可见吸收光谱显示在315–370
• Side-chain effects on phenothiazine-based donor-acceptor copolymer properties in organic photovoltaic devices
  作者：Young-Hoon Seo、Woo-Hyung Lee、Jong-Hyeok Park、Cheolbeom Bae、Yongtaek Hong、Jong-Wook Park、In-Nam Kang

  DOI：10.1002/pola.25074

  日期：2012.2.15

  Solution‐processed field‐effect transistors fabricated with these polymers exhibited p‐type organic thin film transistor characteristics. The field‐effect mobilities of P1 and P2 were measured to be 1.0 × 10−4 and 7.5 × 10−5 cm2 V−1 s−1, respectively, with on/off ratios in the order of 104 for all polymers. A photovoltaic device in which a P2/PC71BM (1/3) blend film was used as the active layer exhibited an open‐circuit

  通过Suzuki偶联反应合成了一系列新的基于吩噻嗪的供体-受体共聚物P1和P2。重均分子量（M wP1和P2的）分别为16,700和16,100，多分散指数分别为1.74和1.39。聚合物薄膜的紫外可见吸收光谱在318-320 nm，430-436 nm和527-568 nm范围内包含三个强吸收带。在320和430 nm处的吸收峰主要源自吩噻嗪基单体单元，而在527–568 nm处更长的波长吸收带归因于聚合物主链的有效共轭长度增加。用这些聚合物制成的溶液处理的场效应晶体管表现出p型有机薄膜晶体管的特性。P1和P2的场效应迁移率测量为1.0×10 -4和7.5×10 -5 cm 2 V -1 s对于所有聚合物，-1分别具有10 4数量级的开/关比。使用P2 / PC 71 BM（1/3）混合膜作为有源层的光伏器件的开路电压（V OC）为0.70 V，短路电流（J SC）为6.79 mA cm
• 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.
• Effect of intermolecular interaction with phenothiazine core on inverted organic photovoltaics by using different acceptor moiety
  作者：Yu-Lung Weng、Yi-Chan Li、Chih-Ping Chen、Yuan Jay Chang

  DOI：10.1016/j.dyepig.2017.07.027

  日期：2017.11

  Six novel small molecules containing phenothiazine as the core moiety of p-type materials were synthesized in combination with PC61BM or PC71BM as n-type materials for bulk heterojunction organic photovoltaic (OPV) cells. Phenothiazine was used as donor building blocks to construct acceptor donor acceptor (A-D-A) and ADD A small molecule. We investigated the relationship between the molecular structures, optoelectronic and thermal properties, and their blend film morphologies for OPV applications. We further studied their photophysical properties using a time-dependent density functional theory model and the B3LYP functional. A solution-processed OPV employing PT2-DE combined with the electron acceptor PC61BM and additive 010 achieved optimal device performance, with a shortcircuit current 'of 6.3 mASix novel small molecules containing phenothiazine as the core moiety of p -type materials were synthesized in combination with PC6113M or PC71BM as n -type materials for bulk heterojunction organic photovoltaic (OPV) cells. Phenothiazine was used as donor building blocks to construct acceptor donor acceptor (A D A) and A D D A small molecule. We investigated the relationship between the molecular structures, optoelectronic and thermal properties, and their blend film morphologies for OPV applications. We further studied their photophysical properties using a time -dependent density functional theory model and the B3LYP functional. A solution -processed OPV employing PT2-DE combined with the electron acceptor PC61BM and additive 010 achieved optimal device performance, with a shortcircuit current 'of 6.3 mA cm -2, an open -circuit voltage of 770 mV, a fill factor of 0.55, and a corresponding overall conversion efficiency of 2.64%. To the best of our knowledge, this is the best -reported performance of a phenothiazine derivative for OPV application. 2017 Elsevier Ltd. All rights reserved. cm(-2), an open-circuit voltage of 770 mV, a fill factor of 0.55, and a corresponding overall conversion efficiency of 2.64%. To the best of our knowledge, this is the best-reported performance of a phenothiazine derivative for OPV application. (C) 2017 Elsevier Ltd. All rights reserved.