3,6-二乙炔基喹啉 | 405313-59-9

• 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
• 中文名称: 3,6-二乙炔基喹啉
• 英文名称: 3,6-diethynylquinoline
• 英文别名: 3,6-Diethynylquinoline
• CAS: 405313-59-9
• 化学式: C₁₃H₇N
• 分子量: 177.205
• InChiKey: JCYWXAYAZPTOJN-UHFFFAOYSA-N

物化性质

• 沸点：
  326.6±22.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-碘苯甲醚 、 3,6-二乙炔基喹啉 在 Pd(PPh₃)Cl₂ 哌啶 、 copper(l) iodide 作用下， 生成 3,6-Bis-(2-methoxy-phenylethynyl)-quinoline
  参考文献：
  名称：

  Quinoline-Containing, Conjugated Poly(aryleneethynylene)s:  Novel Metal and H⁺-Responsive Materials

  摘要：

  We describe the synthesis of novel copolymers containing quinoline, benzene, and alkyne groups by a Pd-catalyzed Heck-Cassar-Sonogashira-Hagihara reaction. Direct iodination of quinoline by a mixture of iodine, potassium periodate, and sulfuric acid in chloroform gives 3,6-diiodoquinoline. 3,6-Diiodoquinoline was coupled to 1,4-diethynyl-2,5-bis(2-ethylhexyl)benzene, and 3,6-diethynylquinoline was coupled to 1,4-diiodo-2,5-bis(2-ethylhexyloxy)benzene. The polymers formed in good-to-excellent yields with a degree of polymerization (P-n) ranging from 11 to 95 and polydispersities (M-w/M-n) from 1.8 to 3.3. Their optical properties (i.e., absorption and emission) were shown to be dramatically dependent upon the presence of protons and to a lesser extent metal cations. The change in fluorescence upon protonation is different for the alkyl- and alkoxy-substituted polymer. In the alkyl case bright yellow fluorescence is observed upon protonation, while for the alkoxy case the polymer's fluorescence is quenched upon addition of acid at polymer concentrations > 0.1 mg L-1.

  DOI：

  10.1021/ma0116654
• 作为产物：
  描述：

  三甲基乙炔基硅 、 3,6-diiodoquinoline 在 Pd(PPh₃)Cl₂ 哌啶 、 copper(l) iodide 、 potassium carbonate 作用下， 生成 3,6-二乙炔基喹啉
  参考文献：
  名称：

  Quinoline-Containing, Conjugated Poly(aryleneethynylene)s:  Novel Metal and H⁺-Responsive Materials

  摘要：

  We describe the synthesis of novel copolymers containing quinoline, benzene, and alkyne groups by a Pd-catalyzed Heck-Cassar-Sonogashira-Hagihara reaction. Direct iodination of quinoline by a mixture of iodine, potassium periodate, and sulfuric acid in chloroform gives 3,6-diiodoquinoline. 3,6-Diiodoquinoline was coupled to 1,4-diethynyl-2,5-bis(2-ethylhexyl)benzene, and 3,6-diethynylquinoline was coupled to 1,4-diiodo-2,5-bis(2-ethylhexyloxy)benzene. The polymers formed in good-to-excellent yields with a degree of polymerization (P-n) ranging from 11 to 95 and polydispersities (M-w/M-n) from 1.8 to 3.3. Their optical properties (i.e., absorption and emission) were shown to be dramatically dependent upon the presence of protons and to a lesser extent metal cations. The change in fluorescence upon protonation is different for the alkyl- and alkoxy-substituted polymer. In the alkyl case bright yellow fluorescence is observed upon protonation, while for the alkoxy case the polymer's fluorescence is quenched upon addition of acid at polymer concentrations > 0.1 mg L-1.

  DOI：

  10.1021/ma0116654

文献信息

• Quinoline-Containing, Conjugated Poly(aryleneethynylene)s:  Novel Metal and H⁺-Responsive Materials
  作者：Carlito G. Bangcuyo、Mary E. Rampey-Vaughn、Lan T. Quan、S. Michael Angel、Mark D. Smith、Uwe H. F. Bunz

  DOI：10.1021/ma0116654

  日期：2002.2.1

  We describe the synthesis of novel copolymers containing quinoline, benzene, and alkyne groups by a Pd-catalyzed Heck-Cassar-Sonogashira-Hagihara reaction. Direct iodination of quinoline by a mixture of iodine, potassium periodate, and sulfuric acid in chloroform gives 3,6-diiodoquinoline. 3,6-Diiodoquinoline was coupled to 1,4-diethynyl-2,5-bis(2-ethylhexyl)benzene, and 3,6-diethynylquinoline was coupled to 1,4-diiodo-2,5-bis(2-ethylhexyloxy)benzene. The polymers formed in good-to-excellent yields with a degree of polymerization (P-n) ranging from 11 to 95 and polydispersities (M-w/M-n) from 1.8 to 3.3. Their optical properties (i.e., absorption and emission) were shown to be dramatically dependent upon the presence of protons and to a lesser extent metal cations. The change in fluorescence upon protonation is different for the alkyl- and alkoxy-substituted polymer. In the alkyl case bright yellow fluorescence is observed upon protonation, while for the alkoxy case the polymer's fluorescence is quenched upon addition of acid at polymer concentrations > 0.1 mg L-1.