(4'-Bromomethyl-4-methyl-β-naphthoate)benzophenone | 215320-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4'-Bromomethyl-4-methyl-β-naphthoate)benzophenone
• CAS: 215320-94-8
• 化学式: C₂₆H₁₉BrO₃
• 分子量: 459.339
• InChiKey: UWRCKXUWDQSQPN-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  613.925±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.393±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  菲-9-甲酸 、 (4'-Bromomethyl-4-methyl-β-naphthoate)benzophenone 在 氢氧化钾 、 水 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 24.0h， 以17.3%的产率得到<4'-(phenanthrene-9-carboxylate)methyl-4-methyl-β-naphthoate>benzophenone
  参考文献：
  名称：

  Singlet−Singlet, Triplet−Triplet, and “Optically-Controlled” Energy Transfer in Polychromophores. Preliminary Models for a Molecular Scale Shift Register

  摘要：

  The photophysics of two trichromophoric molecules have been studied by a combination of absorption, fluorescence, phosphorescence, and laser flash photolysis. TRI-1 consists of phenanthrene and naphthalene terminal chromophores joined to a central biphenyl group by methyl ester bridges. Intramolecular singlet-singlet energy transfer (SSET) between the biphenyl and terminal chromophores occurs efficiently with k(SSET) > 6 x 10(10) s(-1). Longer range SSET from the naphthalene moiety to the phenanthrene group takes place with a lower rate, k similar to 2.5 x 10(8) s(-1). In TRI-2, the biphenyl moiety is replaced by a benzophenone group. SSET here occurs from the phenanthrene chromophore to the central benzophenone chromophore although with a significantly lower rate than the biphenyl --> phenanthrene rate in TRI-1. This is likely due to the change in configuration (pi pi* to n pi*) of the excited singlet states involved in the energy transfer. Triplet-triplet (TTET) energy transfer between biphenyl and the terminal chromophores is not observed as a result of a low biphenyl triplet population. That both the phenanthrene and naphthalene triplets are observed following laser photolysis and have different lifetimes and different excitation wavelength concentration ratios indicates that there is no significant TTET between these two groups on the time scale at which the triplets are decaying. This is attributed to the large interchromophore distance (similar to 12.5 Angstrom) as indicated by modeling studies. In TRI-2, TTET from benzophenone to the terminal chromophores is indicated by both phosphorescence and laser flash photolysis results. Two-laser flash photolysis of the phenanthrene triplet in TRI-1 results in the production of the naphthalene triplet by the following suggested route: (i) production of the upper excited triplet state of the phenanthrene group, (ii) energy transfer to the central biphenyl moiety, and (iii) further energy transfer to the naphthalene chromophore. The utility of this two-laser behavior as the basis for the operation of an optically coupled molecular scale shift register is discussed.

  DOI：

  10.1021/jp9821782
• 作为产物：
  描述：

  4,4'-二甲基二苯甲酮 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (4'-Bromomethyl-4-methyl-β-naphthoate)benzophenone
  参考文献：
  名称：

  Singlet−Singlet, Triplet−Triplet, and “Optically-Controlled” Energy Transfer in Polychromophores. Preliminary Models for a Molecular Scale Shift Register

  摘要：

  The photophysics of two trichromophoric molecules have been studied by a combination of absorption, fluorescence, phosphorescence, and laser flash photolysis. TRI-1 consists of phenanthrene and naphthalene terminal chromophores joined to a central biphenyl group by methyl ester bridges. Intramolecular singlet-singlet energy transfer (SSET) between the biphenyl and terminal chromophores occurs efficiently with k(SSET) > 6 x 10(10) s(-1). Longer range SSET from the naphthalene moiety to the phenanthrene group takes place with a lower rate, k similar to 2.5 x 10(8) s(-1). In TRI-2, the biphenyl moiety is replaced by a benzophenone group. SSET here occurs from the phenanthrene chromophore to the central benzophenone chromophore although with a significantly lower rate than the biphenyl --> phenanthrene rate in TRI-1. This is likely due to the change in configuration (pi pi* to n pi*) of the excited singlet states involved in the energy transfer. Triplet-triplet (TTET) energy transfer between biphenyl and the terminal chromophores is not observed as a result of a low biphenyl triplet population. That both the phenanthrene and naphthalene triplets are observed following laser photolysis and have different lifetimes and different excitation wavelength concentration ratios indicates that there is no significant TTET between these two groups on the time scale at which the triplets are decaying. This is attributed to the large interchromophore distance (similar to 12.5 Angstrom) as indicated by modeling studies. In TRI-2, TTET from benzophenone to the terminal chromophores is indicated by both phosphorescence and laser flash photolysis results. Two-laser flash photolysis of the phenanthrene triplet in TRI-1 results in the production of the naphthalene triplet by the following suggested route: (i) production of the upper excited triplet state of the phenanthrene group, (ii) energy transfer to the central biphenyl moiety, and (iii) further energy transfer to the naphthalene chromophore. The utility of this two-laser behavior as the basis for the operation of an optically coupled molecular scale shift register is discussed.

  DOI：

  10.1021/jp9821782