3-ethenyl-10-n-hexyl-10H-phenothiazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 3-ethenyl-10-n-hexyl-10H-phenothiazine
• 英文别名: 3-Ethenyl-10-hexylphenothiazine；3-ethenyl-10-hexylphenothiazine
• 化学式: C₂₀H₂₃NS
• 分子量: 309.475
• InChiKey: FWDVXSALPQDMMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethenyl-10-n-hexyl-10H-phenothiazine 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 7-{(7-bromo-10-hexyl-10H-phenothiazin-3-yl)ethen-3-yl}-10-hexyl-10H-phenothiazine-3-carboxaldehyde
  参考文献：
  名称：

  Tuning of spacer groups in organic dyes for efficient inhibition of charge recombination in dye-sensitized solar cells

  摘要：

  Most of the studied organic dyes for dye-sensitized solar cell have exhibited low photovoltage due to fast charge recombination. Here, we report on synthetic strategy of organic dye to get high photovoltage. Phenothiazine (PTZ) moieties are incorporated between electron donating triphenylamine (D) and electron accepting cyanoacrylic acid (A) to enhance non-planarity. Compared to one PTZ incorporation (D-PTZ-A), hypsochromic shift in absorption is observed by incorporation of two PTZs (D-PTZ1 PTZ2-A) due to transition from HOMO-1 to LUMO as confirmed by density functional theory (DFT) calculation. D-PTZ1-PTZ2-A shows higher photovoltage (0.804 V) than D-PTZ-A (0.781 V), those which are even higher than that of the ruthenium-based N719-snesitized one (0.775 V). Little difference in electron transport rate is observed for PTZ derivatives and N719, while electron life time is increased in the order of D-PTZ1-PTZ2-A > D-PTZ-A > N719. Retardation of electron recombination is responsible for the high photovoltage, which is associated with bent conformation induced by PTZ spacer group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.04.002
• 作为产物：
  描述：

  10-己基吩噻嗪 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 2,6-二叔丁基苯酚 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 3-ethenyl-10-n-hexyl-10H-phenothiazine
  参考文献：
  名称：

  有机纳米探针鸡尾酒用于活性氧物种的多区域和多色荧光成像。

  摘要：

  次氯酸钠（CLO - ）作为一种高活性氧不仅作为先天宿主防御强大的“守卫者”而且调节炎症相关的病理状态。尽管荧光探针，用于检测CLO的可用性-在细胞中，大多只能检测CLO -在单细胞器，限制能力，全面阐明上CLO的产生不同细胞器的协同作用- 。这项研究提出了多色和C10的multiorganelle成像纳米探针鸡尾酒的方法-细胞。合成了两种具有不同π共轭长度的半导体低聚物，它们都含有吩噻嗪与ClO-特异性反应。但显示出不同的荧光颜色响应。这些传感组件可以自组装到纳米探针中，分别具有靶向细胞溶酶体和线粒体的能力。这些纳米探针形式的混合物的纳米鸡尾酒，其允许CLO的升高水平的同时成像-在溶酶体和线粒体根据下的每个纳米探针的选择性的激励荧光颜色变化。因此，本研究提供了设计用于多局部和多色成像的探针混合物的一般概念。

  DOI：

  10.1002/adfm.201700493

文献信息

• Synthesis and photophysical properties of phenothiazine-labeled conjugated dendrimers
  作者：Xiao-Hang Zhang、Suk-Ho Choi、DongHoon Choi、Kwang-Hyun Ahn

  DOI：10.1016/j.tetlet.2005.06.051

  日期：2005.8

  A novel class of conjugated dendrimers bearing phenothiazines as peripheral groups and phenylenevinylene-group as a core has been synthesized through the Wittig-Horner reaction in moderate to good yield. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Characterization of π-Conjugated Multi-branched Molecules Bearing Carbazole and Phenothiazine Peripheral Groups
  作者：Min Ju Cho、Tae Wan Lee、Jung-Il Jin、Byeong-Kwon Ju、Dong Hoon Choi

  DOI：10.1080/15421400802329236

  日期：2008.9.30

  A novel class of conjugated multi-branched molecules bearing N-hexyl substituted carbazoles and phenothiazine as peripheral groups and [2,4,5-Tris-(diethoxyphosphorylmethyl)benzyl]phosphonic acid diethyl ester core has been synthesized through Horner-Emmons reaction in moderate to good yield. 8HCz-Den and 8HPTz-Den molecules have absorption maxima at 349 and 381 nm in solution states and maximum PL intensities were observed at 434 and 506 nm, respectively. They exhibited good self-film forming properties by solution casting and spin coating. In particular, by doping [2,6-bis(2-(5-(dibutylamino)phenyl)vinyl)-4H-pyran-4-ylidene]propanedinitrile, red emission could be achieved through complete Forster energy transfer process from the light harvesting host to the guest molecule.
• Synthesis and Electrochemical Properties of Pheneothiazine Dendrimers
  作者：Xiao-Hang Zhang、Kigook Song、Kwang-Hyun Ahn、Sung Ik Yang

  DOI：10.1080/15421400601031223

  日期：2007.2.19

  Dendrimers have attracted much attention due to their potential applications in electronics and optoelectronics such as organic light emitting diodes and photovolatics cells. We have synthesized and characterized the electrochemical properties of conjugated dendrimers bearing phenothiazine derivatives as the peripheral group and phenylenevinylene as a core and corresponding monomer systems. We have found that the electrochemical properties and band gaps strongly depend on substituent and generation. These results can be explained in terms of pi-conjugation length changes as a function of generation.
• Organic Nanoprobe Cocktails for Multilocal and Multicolor Fluorescence Imaging of Reactive Oxygen Species
  作者：Chao Yin、Houjuan Zhu、Chen Xie、Lei Zhang、Peng Chen、Quli Fan、Wei Huang、Kanyi Pu

  DOI：10.1002/adfm.201700493

  日期：2017.6

  mitochondria, respectively. The mixture of these nanoprobes forms a nano‐cocktail that allows for simultaneous imaging of elevated level of ClO− in lysosome and mitochondria according to fluorescence color variations under selective excitation of each nanoprobe. Thus, this study provides a general concept to design probe cocktails for multilocal and multicolor imaging.

  次氯酸钠（CLO - ）作为一种高活性氧不仅作为先天宿主防御强大的“守卫者”而且调节炎症相关的病理状态。尽管荧光探针，用于检测CLO的可用性-在细胞中，大多只能检测CLO -在单细胞器，限制能力，全面阐明上CLO的产生不同细胞器的协同作用- 。这项研究提出了多色和C10的multiorganelle成像纳米探针鸡尾酒的方法-细胞。合成了两种具有不同π共轭长度的半导体低聚物，它们都含有吩噻嗪与ClO-特异性反应。但显示出不同的荧光颜色响应。这些传感组件可以自组装到纳米探针中，分别具有靶向细胞溶酶体和线粒体的能力。这些纳米探针形式的混合物的纳米鸡尾酒，其允许CLO的升高水平的同时成像-在溶酶体和线粒体根据下的每个纳米探针的选择性的激励荧光颜色变化。因此，本研究提供了设计用于多局部和多色成像的探针混合物的一般概念。
• Tuning of spacer groups in organic dyes for efficient inhibition of charge recombination in dye-sensitized solar cells
  作者：Mi-Jeong Kim、Yong-Jae Yu、Jong-Hyung Kim、Young-Sam Jung、Kwang-Yol Kay、Soo-Byung Ko、Chang-Ryul Lee、In-Hyuk Jang、Young-Uk Kwon、Nam-Gyu Park

  DOI：10.1016/j.dyepig.2012.04.002

  日期：2012.10

  Most of the studied organic dyes for dye-sensitized solar cell have exhibited low photovoltage due to fast charge recombination. Here, we report on synthetic strategy of organic dye to get high photovoltage. Phenothiazine (PTZ) moieties are incorporated between electron donating triphenylamine (D) and electron accepting cyanoacrylic acid (A) to enhance non-planarity. Compared to one PTZ incorporation (D-PTZ-A), hypsochromic shift in absorption is observed by incorporation of two PTZs (D-PTZ1 PTZ2-A) due to transition from HOMO-1 to LUMO as confirmed by density functional theory (DFT) calculation. D-PTZ1-PTZ2-A shows higher photovoltage (0.804 V) than D-PTZ-A (0.781 V), those which are even higher than that of the ruthenium-based N719-snesitized one (0.775 V). Little difference in electron transport rate is observed for PTZ derivatives and N719, while electron life time is increased in the order of D-PTZ1-PTZ2-A > D-PTZ-A > N719. Retardation of electron recombination is responsible for the high photovoltage, which is associated with bent conformation induced by PTZ spacer group. (C) 2012 Elsevier Ltd. All rights reserved.