phenol β-cyclodextrin complex | 73621-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenol β-cyclodextrin complex
• 英文别名: β-Cyclodextrin*Phenol
• CAS: 73621-01-9
• 化学式: C₆H₆O*C₄₂H₇₀O₃₅
• 分子量: 1229.11
• InChiKey: LLPDSMHSZKEJJP-ZQOBQRRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.84
• 重原子数：
  84.0
• 可旋转键数：
  7.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  574.28
• 氢给体数：
  22.0
• 氢受体数：
  36.0

反应信息

• 作为产物：
  描述：

  β-环糊精 、 苯酚 以 水 为溶剂， 生成 phenol β-cyclodextrin complex
  参考文献：
  名称：

  β-环糊精包合物中甲基化酚的光物理和光化学

  摘要：

  Absorption and induced circular dichroism (ICD) spectra as well as photophysical (fluorescence quantum yield, fluorescence lifetime, and triplet-triplet absorption) and photochemical (hydrated electron formation) properties have been measured in aqueous solutions of phenol, p-cresol, 2,6-dimethylphenol, 3,5-dimethylphenol, 2,4,6-trimethylphenol, and 3,4,5-trimethylphenol in the presence of beta-cyclodextrin and compared to their behaviors in pure aqueous and ethanolic solutions. Complex formation between the phenols and beta-cyclodextrin is evidenced by absorption and ICD spectroscopy. The photophysical and photochemical behaviors of phenol and p-cresol are weakly affected by complexation. In contrast, the fluorescence quantum yields and lifetimes of the dimethyl- and trimethylphenols are markedly increased in the presence of cyclodextrin, in agreement with the formation of 1:1 complexes with distinct photophysical properties. This allows determination of their ground-state association constants, which are somewhat lower than those of phenol and p-cresol. The study of triplet-triplet absorption and hydrated electron formation of the trimethylated phenols shows that intersystem crossing is slowed down by complexation, whereas the efficiency of one-photon hydrated electron formation is drastically reduced. A marked decrease of the rate constant of S1-S0 internal conversion upon complexation is shown to be mainly responsible for the increase of fluorescence lifetimes and quantum yields. These results are discussed in terms of complex structure, in particular of the location of the phenolic OH group near to the rim of the macrocycle, which confers to its environment properties which liken it to that of alcoholic solutions.

  DOI：

  10.1021/j100151a060