4,13-bis[2-(9-anthryloxy)ethyl]-4,13-diaza-[18]crown-6 | 194712-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,13-bis[2-(9-anthryloxy)ethyl]-4,13-diaza-[18]crown-6
• 英文别名: 7,16-Bis(2-anthracen-9-yloxyethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane；7,16-bis(2-anthracen-9-yloxyethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 194712-91-9
• 化学式: C₄₄H₅₀N₂O₆
• 分子量: 702.891
• InChiKey: JCZFXRCALCXMKY-UHFFFAOYSA-N

物化性质

• 沸点：
  881.5±65.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,13-bis[2-(9-anthryloxy)ethyl]-4,13-diaza-[18]crown-6 以 甲醇 为溶剂， 生成 4,21,27,30,35,38-Hexaoxa-1,24-diazanonacyclo[22.8.8.65,12.613,20.05,20.06,11.014,19.041,46.047,52]dopentaconta-6,8,10,14,16,18,41,43,45,47,49,51-dodecaene
  参考文献：
  名称：

  A novel crown ether–cryptand photoswitch

  摘要：

  一种新的光敏双蒽基冠通过可逆的光环化反应形成一种隐色体，正向反应的效率和热逆反应的速度受到阳离子底物存在的影响。

  DOI：

  10.1039/a701989k
• 作为产物：
  描述：

  蒽酮 在 氢氧化钾 、 sodium hydroxide 、 草酰氯 、 potassium carbonate 、 三乙胺 、 diborane(6) 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 、 苯 为溶剂， 反应 16.25h， 生成 4,13-bis[2-(9-anthryloxy)ethyl]-4,13-diaza-[18]crown-6
  参考文献：
  名称：

  Photoinduced Formation of a Cryptand from a Coronand: An Unexpected Switch in Cation Binding Affinity

  摘要：

  Aza-crown ethers 2 and 3 with anthracene-containing pendant arms have been synthesised and characterised. Both compounds bind Group 1 metal cations in solution, forming complexes of 1:1 stoichiometry. The properties of compound 2 and its complexes have been studied by a range of techniques,. including NMR, UV and fluorescence spectroscopy and X-ray crystallography. The pendant arms can adopt either a cis or a trans geometry, the cis geometry favoured with larger cations. The geometry of the complex affects the fluorescence properties of the system, with larger cations giving higher excimer/monomer ratios. Upon irradiation lambda > 300 nm, coronand 2 forms the cryptand 5 through a reversible intramolecular [4pi+4pi] cycloaddition reaction. The rates of the forward and reverse reactions of this photochromic process are cation dependent; in particular the rate of the thermal reverse reaction is decreased by smaller cations and increased by larger cations, especially Rb+. The metal binding constants in methanol for 2 and 5 have been determined, revealing that the cryptand 5 binds Na+ and Rb+ more weakly than crown ether 2 by over two orders of magnitude.

  DOI：

  10.1002/1521-3765(20020802)8:15<3331::aid-chem3331>3.0.co;2-c

文献信息

• A novel crown ether–cryptand photoswitch
  作者：James H. R. Tucker、Henri Bouas-Laurent、Pierre Marsau、Stuart W. Riley、Jean-Pierre Desvergne

  DOI：10.1039/a701989k

  日期：——

  A new photoactive bis-anthracenyl crown undergoes a reversible photocyclisation to form a cryptand, with the efficiency of the forward reaction and the rate of the thermal reverse reaction strongly affected by the presence of cation substrates.

  一种新的光敏双蒽基冠通过可逆的光环化反应形成一种隐色体，正向反应的效率和热逆反应的速度受到阳离子底物存在的影响。
• Photoinduced Formation of a Cryptand from a Coronand: An Unexpected Switch in Cation Binding Affinity
  作者：Gordon McSkimming、James H. R. Tucker、Henri Bouas-Laurent、Jean-Pierre Desvergne、Simon J. Coles、Michael B. Hursthouse、Mark E. Light

  DOI：10.1002/1521-3765(20020802)8:15<3331::aid-chem3331>3.0.co;2-c

  日期：2002.8.2

  Aza-crown ethers 2 and 3 with anthracene-containing pendant arms have been synthesised and characterised. Both compounds bind Group 1 metal cations in solution, forming complexes of 1:1 stoichiometry. The properties of compound 2 and its complexes have been studied by a range of techniques,. including NMR, UV and fluorescence spectroscopy and X-ray crystallography. The pendant arms can adopt either a cis or a trans geometry, the cis geometry favoured with larger cations. The geometry of the complex affects the fluorescence properties of the system, with larger cations giving higher excimer/monomer ratios. Upon irradiation lambda > 300 nm, coronand 2 forms the cryptand 5 through a reversible intramolecular [4pi+4pi] cycloaddition reaction. The rates of the forward and reverse reactions of this photochromic process are cation dependent; in particular the rate of the thermal reverse reaction is decreased by smaller cations and increased by larger cations, especially Rb+. The metal binding constants in methanol for 2 and 5 have been determined, revealing that the cryptand 5 binds Na+ and Rb+ more weakly than crown ether 2 by over two orders of magnitude.