3,7-diethylnyl-10-methyl-10H-phenothiazine | 250347-38-7

• 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: 3,7-diethylnyl-10-methyl-10H-phenothiazine
• 英文别名: 3,7-Diethynyl-10-methylphenothiazine
• CAS: 250347-38-7
• 化学式: C₁₇H₁₁NS
• 分子量: 261.347
• InChiKey: CRCWIBRDCVPXOA-UHFFFAOYSA-N

物化性质

• 熔点：
  141 °C(Solv: ethanol (64-17-5))
• 沸点：
  433.4±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(叠氮基丙基)三乙氧基硅烷 、 3,7-diethylnyl-10-methyl-10H-phenothiazine 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以88%的产率得到10-methyl-3,7-bis(1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazole-4-yl)-10H-phenothiazine
  参考文献：
  名称：

  三唑基共轭（低聚）吩噻嗪建筑材料的合成及电子性能

  摘要：

  铜催化的炔叠氮化物1,3-偶极环加成变体为具有发光和可逆氧化还原特性的共轭三唑基取代的（oligo）吩噻嗪有机硅衍生物提供了高效入口。此外，通过原位共缩合法，制备了几种具有包埋的（低聚）吩噻嗪的代表性介孔MCM-41型二氧化硅杂化材料，并对其结构和电子性质进行了表征。杂化材料也可以被氧化成共价键结合的嵌入自由基阳离子，这些阳离子通过它们的UV / Vis吸收特征和EPR信号来识别。

  DOI：

  10.3390/molecules26102950
• 作为产物：
  描述：

  3,7-bis(2,2-dibromoethenyl)-10-methylphenothiazine 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以100%的产率得到3,7-diethylnyl-10-methyl-10H-phenothiazine
  参考文献：
  名称：

  环炔基吩噻嗪的首次合成和电子性质

  摘要：

  3-单-和3,7-双（炔基化）吩噻嗪7和8可以容易地由相应的吩噻嗪基甲醛来合成。将单炔基化的吩噻嗪7二聚或交叉偶联，以得到显示出大的斯托克斯位移的高荧光性吩噻嗪基封端的氧化还原活性哑铃9和10。根据循环伏安法，化合物9显示出吩噻嗪基部分的强电子偶联。

  DOI：

  10.1016/s0040-4039(99)01402-1

文献信息

• First synthesis and electronic properties of ring-alkynylated phenothiazines
  作者：Thomas J.J. Müller

  DOI：10.1016/s0040-4039(99)01402-1

  日期：1999.9

  3-mono- and 3,7-bis(alkynylated) phenothiazines 7 and 8 can be readily synthesized from the corresponding phenothiazinyl carbaldehydes. The monoalkynylated phenothiazines 7 are dimerized or cross-coupled to give highly fluorescent phenothiazinyl-terminated redox active dumbbells 9 and 10 that display large Stokes shifts. Compound 9 reveals a strong electronic coupling of the phenothiazinyl moieties

  3-单-和3,7-双（炔基化）吩噻嗪7和8可以容易地由相应的吩噻嗪基甲醛来合成。将单炔基化的吩噻嗪7二聚或交叉偶联，以得到显示出大的斯托克斯位移的高荧光性吩噻嗪基封端的氧化还原活性哑铃9和10。根据循环伏安法，化合物9显示出吩噻嗪基部分的强电子偶联。
• Hypercrosslinked phenothiazine-based polymers as high redox potential organic cathode materials for lithium-ion batteries
  作者：Ying Zhang、Panpan Gao、Xinya Guo、Han Chen、Ruiqiang Zhang、Ya Du、Baofeng Wang、Haishen Yang

  DOI：10.1039/d0ra01312a

  日期：——

  Hypercrosslinked conductive polymers with phenothiazine motifs were achieved and studied as organic cathode materials, exhibiting excellent electrochemical performance.

  使用苯并噻嗪基团的超交联导电聚合物作为有机阴极材料，并表现出优异的电化学性能。
• Radical-Enhanced Charge Transport in Single-Molecule Phenothiazine Electrical Junctions
  作者：Junyang Liu、Xiaotao Zhao、Qusiy Al-Galiby、Xiaoyan Huang、Jueting Zheng、Ruihao Li、Cancan Huang、Yang Yang、Jia Shi、David Zsolt Manrique、Colin J. Lambert、Martin R. Bryce、Wenjing Hong

  DOI：10.1002/anie.201707710

  日期：2017.10.9

  Single-molecule conductances of phenothiazine radicals have been measured using the mechanically controllable break junction technique. Triggered by an acid oxidant, the radical cation of phenothiazine enhances the charge-transport property by up to 200 times with high stability and high junction formation probability at room temperature, which leads to promising applications in single-molecule electronics

  吩噻嗪自由基的单分子电导率已使用机械可控的断裂连接技术进行了测量。吩噻嗪的自由基阳离子受酸氧化剂的触发，在室温下具有高稳定性和高结形成几率，可将电荷传输性能提高200倍，这在单分子电子学和自旋电子学中具有广阔的应用前景。
• Synthesis of Functionalized Ethynylphenothiazine Fluorophores
  作者：Christa S. Krämer、Kirsten Zeitler、Thomas J. J. Müller

  DOI：10.1021/ol0066328

  日期：2000.11.1

  [GRAPHICS]Alkynylated and butadiynyl-bridged phenothiazines with variable functionalization can be synthesized in good yields by cross coupling and condensation approaches. In addition, the structure of the diethynylated phenothiazine (7a) has been corroborated by an X-ray structure analysis. These oligofunctional heterocycles are fluorescent with modest quantum yields (Phi (f) = 20-35%) and represent suitable building blocks for novel photoexcitable molecular wires.
• Synthesis, Electronic Properties, and Self-Assembly on Au{111} of Thiolated Phenylethynyl Phenothiazines
  作者：Christa S. Barkschat、Svetlana Stoycheva、Michael Himmelhaus、Thomas J. J. Müller

  DOI：10.1021/cm901514t

  日期：2010.1.12

  Thiolated phenylethynyl phenothiazines can be regarded as redox-active "alligator clips". They are readily synthesized from ethynyl phenothiazines and show intense blue-green luminescence upon ultraviolet (UV) excitation. Cyclic voltammetry reveals reversible oxidation, also after the chemisorption of in Situ liberated thiols on gold electrodes. The chemisorption on Au111} was studied by ellipsometry, contact angle measurements, X-ray photoelectron spectroscopy, and infrared reflection absorption spectroscopy, and the obtained data support the formation of self-assembled monolayers, depending on the structure of the Substrates. These findings classify them as promising candidates for molecular wires switchable by redox manipulation.