2,7-dimethoxy-3,6-diethynylnaphthalene | 1426232-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,7-dimethoxy-3,6-diethynylnaphthalene
• CAS: 1426232-34-9
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: BEZLOPRCTWYBKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-硝基碘苯 、 2,7-dimethoxy-3,6-diethynylnaphthalene 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以36%的产率得到2,7-dimethoxy-3,6-bis((4-nitrophenyl)ethynyl)naphthalene
  参考文献：
  名称：

  Unique solvent-dependent fluorescence of nitro-group-containing naphthalene derivatives with weak donor–strong acceptor system

  摘要：

  We synthesized nitro-group-containing pi-conjugated naphthalene derivatives with a weak donor-strong acceptor system and investigated their photophysical properties. The nitro group was introduced into naphthalene through the phenyl or phenylethynyl moiety at the C2 and C7 positions as the strong acceptor moiety, and a methoxy group was introduced into naphthalene directly at the position opposite to the nitro group, as a weak donor moiety. While 2-(4-nitrophenyl)naphthalene did not show fluorescence in various solvents, 2-methoxy-6-(4-nitrophenyl)naphthalene showed fluorescence in weakly polar solvents (Phi(F) = 0.11 in CH2Cl2), with a large Stokes shift (Delta nu = 12,000 cm(-1)). Additionally, 2-methoxy-6-(4-nitrophenyl)naphthalene did not show fluorescence in polar solvents (acetonitrile) and non-polar solvents (toluene). This unique solvent-dependent fluorescence is remarkable for environmental fluorescence sensor applications. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.096
• 作为产物：
  描述：

  2,7-二溴-3,6-二甲氧基-萘 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 2,7-dimethoxy-3,6-diethynylnaphthalene
  参考文献：
  名称：

  Unique solvent-dependent fluorescence of nitro-group-containing naphthalene derivatives with weak donor–strong acceptor system

  摘要：

  We synthesized nitro-group-containing pi-conjugated naphthalene derivatives with a weak donor-strong acceptor system and investigated their photophysical properties. The nitro group was introduced into naphthalene through the phenyl or phenylethynyl moiety at the C2 and C7 positions as the strong acceptor moiety, and a methoxy group was introduced into naphthalene directly at the position opposite to the nitro group, as a weak donor moiety. While 2-(4-nitrophenyl)naphthalene did not show fluorescence in various solvents, 2-methoxy-6-(4-nitrophenyl)naphthalene showed fluorescence in weakly polar solvents (Phi(F) = 0.11 in CH2Cl2), with a large Stokes shift (Delta nu = 12,000 cm(-1)). Additionally, 2-methoxy-6-(4-nitrophenyl)naphthalene did not show fluorescence in polar solvents (acetonitrile) and non-polar solvents (toluene). This unique solvent-dependent fluorescence is remarkable for environmental fluorescence sensor applications. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.096