5,11,17,23-tetra-tert-butyl-25-mono-[(6'-methoxynaphthalen-2'-yl)-carbonylmethoxy]calix[4]arene | 392675-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,11,17,23-tetra-tert-butyl-25-mono-[(6'-methoxynaphthalen-2'-yl)-carbonylmethoxy]calix[4]arene
• CAS: 392675-53-5
• 化学式: C₅₇H₆₆O₆
• 分子量: 847.147
• InChiKey: RRDDGNZAEVIBMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.09
• 重原子数：
  63.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  96.22
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  溴乙酸乙酯 、 5,11,17,23-tetra-tert-butyl-25-mono-[(6'-methoxynaphthalen-2'-yl)-carbonylmethoxy]calix[4]arene 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以67%的产率得到5,11,17,23-tetra-tert-butyl-25-mono-[(6'methoxynaphthalen-2'-yl)carbonylmethoxy]-26,27,28-tris(ethoxycarbonylmethoxy)calix[4]arene
  参考文献：
  名称：

  Synthesis and Photophysical and Cation-Binding Properties of Mono- and Tetranaphthylcalix[4]arenes as Highly Sensitive and Selective Fluorescent Sensors for Sodium

  摘要：

  The syntheses and properties of two calixarene-based fluorescent molecular sensors are reported. These comprise tert-butylcalix[4]arene either with one appended fluorophore and three ester groups (Calix-AMN1), or with four appended fluorophores (Calix-AMN4). The fluorophore is 6-acyl-2-methoxy-naphthalene (AMN), which contains an electron-donating substituent (methoxy group) conjugated to an electron-withdrawing substituent (carbonyl group); this allows photoinduced charge transfer (PCT) to occur upon excitation. The investigated fluoroionophores thus belong to the family of PCT fluorescent molecular sensors. In addition to the expected red shifts of the absorption and emission spectra upon cation binding, a drastic enhancement of the fluorescence quantum yield-in an "off-on" fashion comparable to that seen in photoinduced electron transfer (PET) molecular sensors-was observed. For Calix-AMN1, it increases from 10(-3) for the free ligand to 0.68 for the complex with Ca2+. This exceptional behaviour can be interpreted in terms of the relative locations of the n pi* and pi pi* levels, which depend on the charge density of the bound cation. For Calix-AMN4, in addition to the photophysical effects observed for Calix-AMN1, interactions between the chromophores by complexation with some cations have been found in the ground state (hypochromic effect) and in the excited state (excimer formation). Steady-state fluorescence anisotropy measurements for the system Na+ subset of Calix-AMN4, show a depolarization effect due to energy transfer (homotransfer) between the fluorophores. Regarding the complexing properties, a high selectivity for Na+ over K+, Li+, Ca2+ and Mg2+ was observed in ethanol and ethanol-water mixtures. The selectivity (Na+/other cations) expressed as the ratio of the stability constants was found to be more than 400.

  DOI：

  10.1002/1521-3765(20011105)7:21<4590::aid-chem4590>3.0.co;2-a
• 作为产物：
  描述：

  2-萘甲醚 在 三氯化铝 、 potassium hydrogencarbonate 作用下， 以 硝基苯 、 丙酮 为溶剂， 反应 50.33h， 生成 5,11,17,23-tetra-tert-butyl-25-mono-[(6'-methoxynaphthalen-2'-yl)-carbonylmethoxy]calix[4]arene
  参考文献：
  名称：

  Synthesis and Photophysical and Cation-Binding Properties of Mono- and Tetranaphthylcalix[4]arenes as Highly Sensitive and Selective Fluorescent Sensors for Sodium

  摘要：

  The syntheses and properties of two calixarene-based fluorescent molecular sensors are reported. These comprise tert-butylcalix[4]arene either with one appended fluorophore and three ester groups (Calix-AMN1), or with four appended fluorophores (Calix-AMN4). The fluorophore is 6-acyl-2-methoxy-naphthalene (AMN), which contains an electron-donating substituent (methoxy group) conjugated to an electron-withdrawing substituent (carbonyl group); this allows photoinduced charge transfer (PCT) to occur upon excitation. The investigated fluoroionophores thus belong to the family of PCT fluorescent molecular sensors. In addition to the expected red shifts of the absorption and emission spectra upon cation binding, a drastic enhancement of the fluorescence quantum yield-in an "off-on" fashion comparable to that seen in photoinduced electron transfer (PET) molecular sensors-was observed. For Calix-AMN1, it increases from 10(-3) for the free ligand to 0.68 for the complex with Ca2+. This exceptional behaviour can be interpreted in terms of the relative locations of the n pi* and pi pi* levels, which depend on the charge density of the bound cation. For Calix-AMN4, in addition to the photophysical effects observed for Calix-AMN1, interactions between the chromophores by complexation with some cations have been found in the ground state (hypochromic effect) and in the excited state (excimer formation). Steady-state fluorescence anisotropy measurements for the system Na+ subset of Calix-AMN4, show a depolarization effect due to energy transfer (homotransfer) between the fluorophores. Regarding the complexing properties, a high selectivity for Na+ over K+, Li+, Ca2+ and Mg2+ was observed in ethanol and ethanol-water mixtures. The selectivity (Na+/other cations) expressed as the ratio of the stability constants was found to be more than 400.

  DOI：

  10.1002/1521-3765(20011105)7:21<4590::aid-chem4590>3.0.co;2-a