3-bromo-10-ethyl-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-bromo-10-ethyl-10H-phenothiazine
• 英文别名: 3-Brom-10-ethyl-phenothiazin；3-Bromo-10-ethylphenothiazine
• 化学式: C₁₄H₁₂BrNS
• 分子量: 306.226
• InChiKey: IBUMOIPXUUURJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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-bromo-10-ethyl-10H-phenothiazine 在 盐酸 、 potassium chloride 、 四丁基醋酸铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 (E)-3-(10-ethyl-10H-phenothiazin-3-yl)-2-propenal
  参考文献：
  名称：

  Synthesis of electroactive hydrazones derived from 3-(10-alkyl-10H-phenothiazin-3-yl)-2-propenals and their corresponding 3,3′-bispropenals

  摘要：

  3-(10-Alkyl-10H-phenothiazin-3-yl)-2-propenals and their corresponding 3,3'-bispropenals that represent a previously unexplored class of functionalised phenothiazine derivatives were prepared upon reacting N-alkylated 3-bromo- and 3,7-dibromo-10H-phenothiazines with acrolein diethyl acetal under Pd catalysis. The obtained heterocyclic 2,3-unsaturated aldehydes were condensed with N-methyl-N-phenylhydrazine and N,N-diphenylhydrazine resulting in mono- and dihydrazones that act as effective hole transporting materials. Thermal, optical, electrochemical and photophysical properties of the synthesised new organic electroactive derivatives have been investigated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.010
• 作为产物：
  描述：

  吩噻嗪 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydroxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 3-bromo-10-ethyl-10H-phenothiazine
  参考文献：
  名称：

  基于聚集诱导的发射以及混合的局部和电荷转移状态的高效红色荧光OLED

  摘要：

  受能隙定律和大共轭结构的限制，红色有机发光二极管（OLED）长期以来一直因效率问题而受到批评。聚集诱导发射（AIE）效应和逆系统间交叉过程可导致高光致发光量子产率（PLQYs）和高激子利用效率（EUE），这是获得高效OLED的两个关键目标。在这项工作中，我们选择苯并噻二唑作为受体（A），并选择三苯胺和吩噻嗪作为供体（Ds）设计和合成D–A–D红色荧光分子PBTPA。系统的光物理测量结果表明PBTPA表现出AIE趋势，表现为聚集体诱导的发射增强以及混合的局部和电荷转移（HLCT）状态的特征。这些特征有助于实现高固态发光效率和高激子利用率。使用PBTPA制造的非掺杂器件在656 nm处显示红色电致发光峰，对应于国际照明委员会的坐标为（0.65，0.32），外部量子效率为1.62％。通过计算，EUE达到了50％的值。根据理论计算结果，第二三重态之间的有效热激子通道（T2）和最低的单重态（S 1）

  DOI：

  10.1016/j.dyepig.2020.108770

文献信息

• Organophotoredox assisted cyanation of bromoarenes <i>via</i> silyl-radical-mediated bromine abstraction
  作者：Maniklal Shee、Sk. Sheriff Shah、N. D. Pradeep Singh

  DOI：10.1039/d0cc00163e

  日期：——

  The insertion of a nitrile (–CN) group into arenes through the direct functionalization of the C(sp2)–Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed

  通过C（sp 2）-Br键的直接官能化将腈基（–CN）插入芳烃中是一项具有挑战性的反应。本文中，我们报道了使用有机光氧化还原催化剂4CzIPN和甲苯磺酰氰（TsCN）作为腈源的有机光氧化还原方法，用于芳基溴化物的氰化。通过单电子转移（SET）机制，将光生甲硅烷基自由基用于从芳基溴化物中提取溴，以提供芳基基团，该芳基基团同时被TsCN拦截以提供芳族腈。已证明一系列包含给电子和吸电子基团的底物在室温下以良好的产率进行氰化。
• Phenothiazine-based benzoxazole derivates exhibiting mechanochromic luminescence: the effect of a bromine atom
  作者：Pengchong Xue、Boqi Yao、Jiabao Sun、Qiuxia Xu、Peng Chen、Zhenqi Zhang、Ran Lu

  DOI：10.1039/c4tc00061g

  日期：——

  The mechanochromism of two phenothiazine-based benzoxazole derivates (PVB and BPVB) was compared. The ground film of PVB without bromine atoms can self-cure within 15 min at room temperature, while the ground film for BPVB showed no changes for at least 2 weeks.

  两种基于苯并噻唑的苯并噻唑衍生物（PVB和BPVB）的机械致色性进行了比较。不含溴原子的PVB基膜在室温下可以在15分钟内自行固化，而BPVB的基膜至少两周内没有任何变化。
• Ratiometric Polymer Probe for Detection of Peroxynitrite and the Application for Live-Cell Imaging
  作者：Hio Kuan Lao、Jingyun Tan、Chunfei Wang、Xuanjun Zhang

  DOI：10.3390/molecules24193465

  日期：——

  Peroxynitrite (ONOO−) is one of the sources of oxidation stress involved in many biological signaling pathways. The role of ONOO− being a double-edged sword in biological systems drives the development of effective detection tools. In this work, a boronate-based polymeric fluorescent probe PB-PVA was synthesized and the probe performance was evaluated. The probe exhibits ratiometric sensing of ONOO−

  过氧亚硝酸盐 (ONOO−) 是许多生物信号通路中氧化应激的来源之一。ONOO− 在生物系统中作为一把双刃剑的作用推动了有效检测工具的发展。在这项工作中，合成了一种基于硼酸盐的聚合物荧光探针 PB-PVA，并对探针性能进行了评估。该探针在 0–6 µM 范围内表现出 ONOO− 的比率传感。探针荧光强度比与ONOO-浓度之间存在良好的线性关系。与其他 ROS 相比，该探针还显示出对 ONOO− 的中等选择性。此外，它是水溶性的并且具有良好的生物相容性，这有助于 ONOO− 在活细胞中的成像。这些特性可以使探针成为与 ONOO-相关的体外研究中很有前景的工具。
• Two novel blue phosphorescent host materials containing phenothiazine-5,5-dioxide structure derivatives
  作者：Feng-Ming Xie、Qingdong Ou、Qiang Zhang、Jiang-Kun Zhang、Guo-Liang Dai、Xin Zhao、Huai-Xin Wei

  DOI：10.3762/bjoc.14.73

  日期：——

  Two novel D–A bipolar blue phosphorescent host materials based on phenothiazine-5,5-dioxide: 3-(9H-carbazol-9-yl)-10-ethyl-10H-phenothiazine-5,5-dioxide (CEPDO) and 10-butyl-3-(9H-carbazol-9-yl)-10H-phenothiazine-5,5-dioxide (CBPDO) were synthesized and characterized. The photophysical, electrochemical and thermal properties were systematically investigated. CEPDO and CBPDO not only have a high triplet energy but also show a bipolar behavior. Moreover, their fluorescence emission peaks are in the blue fluorescence region at 408 nm and the fluorescence quantum efficiency (Φ) of CEPDO and CBPDO were 62.5% and 59.7%, respectively. Both CEPDO and CBPDO showed very high thermal stability with decomposition temperatures (T_d) of 409 and 396 °C as well as suitable HOMO and LUMO energy levels. This preferable performance suggests that CEPDO and CBPDO are alternative bipolar host materials for the PhOLEDs.

  基于苯噻嗪-5,5-二氧化物的两种新型D-A双极蓝色磷光主体材料：3-(9H-咔唑-9-基)-10-乙基-10H-苯噻嗪-5,5-二氧化物（CEPDO）和10-丁基-3-(9H-咔唑-9-基)-10H-苯噻嗪-5,5-二氧化物（CBPDO）已合成并表征。系统研究了它们的光物理、电化学和热性质。CEPDO和CBPDO不仅具有高三重态能量，还表现出双极行为。此外，它们的荧光发射峰位于408纳米的蓝色荧光区域，CEPDO和CBPDO的荧光量子效率（Φ）分别为62.5%和59.7%。CEPDO和CBPDO均表现出非常高的热稳定性，分解温度（Td）分别为409°C和396°C，以及适当的HOMO和LUMO能级。这种优越的性能表明CEPDO和CBPDO是PhOLEDs的替代双极主体材料。
• Synthesis and Properties of Imidazole-p-phenothiazine Derivatives as Light-Emitting and Ambipolar Materials
  作者：Jing Shao、Xin Zhao、Xing He、Zhengyin Zhang、Rongjia Zhai

  DOI：10.14233/ajchem.2014.17308

  日期：——

  Novel phenothiazine derivatives were designed and synthesized for application as electroluminescent materials. They were characterized by means of 1H, 13C NMR and FTIR. The optical, electrochemical and thermal properties were also investigated. The relationship between the chemical structure and the properties of these materials was evaluated. Due to the introduction of thiophene ring, these compounds exhibited efficient emission from blue to green and red shifs in absorption and photoluminescence spectra. With respect to thermal properties and the oxidation potentials, it can be turned by varying the conjugation length of compounds and the length of alkyl chains. Mostly, all four compounds had suited HOMO and LUMO energy levels which can be used not only hole-transporting but also electron-tansporting materials in organic light-emitting devices.

  新型苯噻嗪衍生物被设计和合成用于作为电致发光材料。通过1H、13C NMR和FTIR对其进行了表征。还研究了其光学、电化学和热特性。评估了化学结构与这些材料性质之间的关系。由于引入了噻吩环，这些化合物表现出从蓝光到绿色的高效发射，并在吸收和荧光光谱中出现红移。在热性能和氧化电位方面，可以通过改变化合物的共轭长度和烷基链的长度进行调节。总体而言，这四种化合物均具有适宜的HOMO和LUMO能级，可以作为有机发光器件中的孔传输材料和电子传输材料。