4-(5-bromothiophen-3-yl)pyrrolo[1,2-a]quinoxaline | 1287776-15-1

• 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: 4-(5-bromothiophen-3-yl)pyrrolo[1,2-a]quinoxaline
• CAS: 1287776-15-1
• 化学式: C₁₅H₉BrN₂S
• 分子量: 329.22
• InChiKey: IVJJZBHUCZLSCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-噻吩硼酸 、 4-(5-bromothiophen-3-yl)pyrrolo[1,2-a]quinoxaline 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium hydrogencarbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到4-((5-thiophen-2-yl)thiophen-3-yl)pyrrolo[1,2-a]quinoxaline
  参考文献：
  名称：

  Synthesis of a novel fluorescent and ion sensitive monomer bearing quinoxaline moieties and its electropolymerization

  摘要：

  A novel terthienyl based fluorescent polymer bearing pendant quinoxaline moieties directly attached to the 3-positions of the central thiophene ring was synthesized by electrochemical polymerization of 4-((2,5-dithiophen-2-yl)thiophen-3-yl)pyrrolo[1,2-a]quinoxaline (TT-Q). The corresponding polymer was characterized by cyclic voltammetry, FT-IR and UV-vis spectroscopy. The polymer exhibits a reversible redox behavior (Ep(1/2) = 1.05 V) accompanied with a reversible electrochromic behavior; yellowish orange in the neutral state and green in the oxidized state. Band gap of polymer was found (E-g = 1.94 eV). Moreover, the sensitivity of both the monomer and its polymer towards metal cations was investigated by monitoring the change in the fluorescence intensity. Among various common ions, both the monomer and its polymer were found to be selective towards Fe3+ ions by quenching the fluorescence efficiency with a Stern-Volmer constant (K-sv) of (2.7 x 10(3) M-1) and (5.0 x 10(3) M-1) for monomer and polymer solutions, respectively. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.reactfunctpolym.2011.02.008
• 作为产物：
  描述：

  4-(thiophen-3-yl)pyrrolo[1,2-a]quinoxaline 在 溴 作用下， 以 溶剂黄146 为溶剂， 以76%的产率得到4-(5-bromothiophen-3-yl)pyrrolo[1,2-a]quinoxaline
  参考文献：
  名称：

  Synthesis of a novel fluorescent and ion sensitive monomer bearing quinoxaline moieties and its electropolymerization

  摘要：

  A novel terthienyl based fluorescent polymer bearing pendant quinoxaline moieties directly attached to the 3-positions of the central thiophene ring was synthesized by electrochemical polymerization of 4-((2,5-dithiophen-2-yl)thiophen-3-yl)pyrrolo[1,2-a]quinoxaline (TT-Q). The corresponding polymer was characterized by cyclic voltammetry, FT-IR and UV-vis spectroscopy. The polymer exhibits a reversible redox behavior (Ep(1/2) = 1.05 V) accompanied with a reversible electrochromic behavior; yellowish orange in the neutral state and green in the oxidized state. Band gap of polymer was found (E-g = 1.94 eV). Moreover, the sensitivity of both the monomer and its polymer towards metal cations was investigated by monitoring the change in the fluorescence intensity. Among various common ions, both the monomer and its polymer were found to be selective towards Fe3+ ions by quenching the fluorescence efficiency with a Stern-Volmer constant (K-sv) of (2.7 x 10(3) M-1) and (5.0 x 10(3) M-1) for monomer and polymer solutions, respectively. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.reactfunctpolym.2011.02.008