2,6-bis(2,2-dibromoethenyl)naphthalene | 610283-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-bis(2,2-dibromoethenyl)naphthalene
• CAS: 610283-01-7
• 化学式: C₁₄H₈Br₄
• 分子量: 495.834
• InChiKey: PHJWUJCRPXCSBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.02
• 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：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  苯乙炔 、 2,6-bis(2,2-dibromoethenyl)naphthalene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 甲醇 、 三乙胺 为溶剂， 反应 3.0h， 以57%的产率得到2,6-bis[4-phenyl-2-(phenylethylnyl)but-1-en-3-ynyl]naphthalene
  参考文献：
  名称：

  Synthesis and Photophysical Studies of Bis-enediynes as Tunable Fluorophores

  摘要：

  We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the T-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.

  DOI：

  10.1021/ja0349148
• 作为产物：
  描述：

  2,6-双(羟基甲基)萘 在 三苯基膦 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,6-bis(2,2-dibromoethenyl)naphthalene
  参考文献：
  名称：

  Synthesis and Photophysical Studies of Bis-enediynes as Tunable Fluorophores

  摘要：

  We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the T-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.

  DOI：

  10.1021/ja0349148