11-fluorodibenzo[a,c]phenazine | 439-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 11-fluorodibenzo[a,c]phenazine
• 英文别名: 11-Fluorophenanthro[9,10-b]quinoxaline；11-fluorophenanthro[9,10-b]quinoxaline
• CAS: 439-20-3
• 化学式: C₂₀H₁₁FN₂
• 分子量: 298.319
• InChiKey: SPKGPWOHUZUXPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  吩噻嗪 、 11-fluorodibenzo[a,c]phenazine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72 %的产率得到10-(dibenzo[a,c]phenazin-11-yl)-10H-phenothiazine
  参考文献：
  名称：

  Strategic Insertion of Heavy Atom to Tailor TADF OLED Material for the Development of Type I Photosensitizing Catalytic Red Emissive Assemblies

  摘要：

  The work presented in the manuscript describes a simple strategy for transforming thermally activated delayed fluorescent organic light‐emitting diodes (TADF OLEDs) compound 10‐(dibenzo[a,c]phenazin‐11‐yl)‐10H‐phenoxazine (DPZ‐PXZ) into type I photosensitizer 10‐(dibenzo[a,c]phenazin‐11‐yl)‐10H‐phenothiazine (DPZ‐PHZ) by strategically introducing sulfur atom in the photosensitizing core. The synthesized compound DPZ‐PHZ exhibits aggregation‐induced enhancement (AIE) and through‐space charge transfer (TSCT) characteristics and generates red emissive assemblies in mixed aqueous media. The original compound DPZ‐PXZ exhibits well‐separated HOMO and LUMO levels and is reported to have highly efficient reverse intersystem crossing (RISC). In comparison, the incorporation of sulfur atom in the phenothiazine donor regulates the electronic communication between donor and acceptor units and promotes the intersystem crossing (ISC) in DPZ‐PHZ molecules. Interestingly, compound DPZ‐PHZ exhibits rapid activation of aerial oxygen for instant generation of superoxide radical anion. Backed by excellent type I photosensitizing activity, DPZ‐PHZ assemblies have high catalytic potential for the synthesis of benzimidazoles, benzothiazoles and quinazolines derivatives under mild reaction conditions. The work presented in the manuscript provides an insight into the combination of heavy atom approach and TSCT for achieving adequate electronic communication between donor and acceptor units, balanced RISC/ISC, and stabilized‐charge separated state for the development of efficient type I photosensitizing assemblies.

  DOI：

  10.1002/asia.202400033
• 作为产物：
  描述：

  4-氟-2-硝基苯胺 在 乙醇 、 溶剂黄146 、 铂 作用下， 生成 11-fluorodibenzo[a,c]phenazine
  参考文献：
  名称：

  604.所谓的“ 1-氟-3：4-二硝基苯”。

  摘要：

  DOI：

  10.1039/jr9530003042

文献信息

• In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature
  作者：Kashyap J. Tamuli、Shyamalendu Nath、Manobjyoti Bordoloi

  DOI：10.1002/jhet.4231

  日期：2021.4

  Substituted quinoxaline derivatives are traditionally synthesized by co‐condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o‐phenylenediamine and 1,2‐diketones using cheap and biodegradable itaconic acid as a mild acid

  取代的喹喔啉衍生物传统上是通过各种起始原料的共缩合反应合成的。在本文中，我们描述了一种新型的环境友好的水合成路线，用于合成结构和电子形式多样的90喹喔啉类化合物，并容易获得取代的邻氨基苯甲酸。苯二胺和1,2-二酮在1小时内使用廉价且可生物降解的衣康酸作为温和的酸性促进剂。该反应在室温下进行，该过程通过环缩合反应进行，然后获得上述含氮杂环加合物，而无需进行柱色谱分离，总收率不超过96％。催化剂的简单性，高效率和可重复使用性将该反应条件称为“绿色合成”，这使其可用于克级至克级的合成转化中。
• One-pot synthesis of quinoxalines from reductive coupling of 2-nitroanilines and 1,2-diketones using indium
  作者：Ahra Go、Geunsoo Lee、Jaeho Kim、Seolhee Bae、Byung Min Lee、Byeong Hyo Kim

  DOI：10.1016/j.tet.2015.01.007

  日期：2015.2

  reduction-cyclization of 2-nitroanilines and 1,2-diketones to give quinoxalines was investigated. Using indium and an appropriate acid such as acetic acid or indium(III) chloride, various quinoxaline derivatives including 2,3-dialkylquinoxalines, 2,3-diphenylquinoxalines, 2,3-di-2-thiophenylquinoxalines, 2,3-di(pyridin-2-yl)quinoxalines, and dibenzo[a,c]phenazines were synthesized in moderate to excellent

  研究了2-硝基苯胺和1,2-二酮的一锅还原环化反应生成喹喔啉。使用铟和适当的酸，例如乙酸或氯化铟（III），各种喹喔啉衍生物包括2,3-二烷基喹喔啉，2,3-二苯基喹喔啉，2,3-二-2-硫代苯基喹喔啉，2,3-二（吡啶） -2-基）喹喔啉和二苯并[ a，c ]吩嗪以中等至优异的产率合成。