3-hydroxy-2-(2-thienyl)benzo[g]quinolin-4(1H)-one | 1185734-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-hydroxy-2-(2-thienyl)benzo[g]quinolin-4(1H)-one
• 英文别名: 3-hydroxy-2-thiophen-2-yl-1H-benzo[g]quinolin-4-one
• CAS: 1185734-93-3
• 化学式: C₁₇H₁₁NO₂S
• 分子量: 293.346
• InChiKey: CMQKZFLPFQSOKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 polyphosphoric acid 作用下， 反应 2.0h， 生成 3-hydroxy-2-(2-thienyl)benzo[g]quinolin-4(1H)-one
  参考文献：
  名称：

  3-Hydroxybenzo[g]quinolones: dyes with red-shifted absorption and highly resolved dual emission

  摘要：

  New derivatives of 3-hydroxyquinolone (3HQ) with a fused benzene ring (3-hydroxybenzo[g]quinolones) have been synthesized. They display a remarkable red shift of their absorption spectrum in comparison with other 3HQ analogs allowing their excitation by common He/Cd and Ar-ion lasers. As a result of their irreversible excited-state intramolecular proton transfer (ESIPT) reaction, they display a dual fluorescence in a series of solvents of varying polarities, starting from toluene to methanol. The dual emission of these dyes correlates well with solvent H-bond basicity, which is connected with the effect of this solvent property on the kinetics of the ESIPT reaction. In addition to their red-shifted absorption and fluorescence, these new derivatives show a larger separation of their two emission bands and a more appropriate range of their intensity ratio than the previously synthesized 3HQs. These properties allow an improved ratiometric evaluation of the local H-bond basicity of unknown environments, which will favor future applications of the new dyes in polymer and biological sciences. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.024