(E,E)-1,4-Bis(3,5-di-tert-butylstyryl)naphthalene | 142534-22-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-1,4-Bis(3,5-di-tert-butylstyryl)naphthalene
• CAS: 142534-22-3
• 化学式: C₄₂H₅₂
• 分子量: 556.875
• InChiKey: UHAULYUAIHGFAP-XPWSMXQVSA-N

物化性质

• 沸点：
  631.8±55.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.37
• 重原子数：
  42.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (E,E)-1,4-Bis(3,5-di-tert-butylstyryl)naphthalene 在 2,3-丁二酮 作用下， 生成 (Z,E)-1,4-Bis(3,5-di-tert-butylstyryl)naphthalene
  参考文献：
  名称：

  Triplet state 1- and 2-fold cis-trans isomerization of bis(styryl)arenes - balance between diabatic and adiabatic mechanisms

  摘要：

  The mechanism for triplet-sensitized cis-trans photoisomerization of three bisstyrylarenes, 1-3, has been studied by quantum yield measurements and laser flash photolysis. The triplet-state lifetimes for all three molecules are long enough to give an isomerization pattern essentially determined by the thermodynamics of the triplet excited-state surface, that is, equilibration processes are much faster than decay processes. Decay from the triplet excited-state surface occurs to various degrees from two equilibrated states, the planar 3E,E* and another with one double bond twisted, 3E,p*. Extension of pi-conjugation gives more 2-fold cis-trans isomerization, from the Z,Z isomer to the E,E isomer, due to aa more facile adiabatic than diabatic pathway for the isomerization reaction. For one of the molecules, 9,10-bisstyrylanthracene, 3, the Z,Z isomer undergoes exclusively 2-fold isomerization to yield the E,E isomer. 1,4-Bis(3,5-di-tert-butylstyryl)naphthalene, 2, shows mainly 2-fold isomerization from the Z,Z isomer, but there is also a diabatic contribution to this isomerization giving a photostationary state, ZE:EE, 18:82. For 4,4'-bis(3,5-di-tert-butylstyryl)biphenyl, 1, the isomerization is still partly adiabatic. There is no decay from the 3Z,p* but all decay occurs from 3E,p*, giving a photostationary state ZE:EE, ca. 50:50. The photostationary states for the bisstyrylnaphthalene and the bisstyrylbiphenyl can be affected by the addition of aa triplet quencher, azulene or perylene, to give almost pure E,E.

  DOI：

  10.1021/j100196a034
• 作为产物：
  描述：

  (Z,E)-1,4-Bis(3,5-di-tert-butylstyryl)naphthalene 在 2,3-丁二酮 作用下， 生成 (E,E)-1,4-Bis(3,5-di-tert-butylstyryl)naphthalene
  参考文献：
  名称：

  Triplet state 1- and 2-fold cis-trans isomerization of bis(styryl)arenes - balance between diabatic and adiabatic mechanisms

  摘要：

  The mechanism for triplet-sensitized cis-trans photoisomerization of three bisstyrylarenes, 1-3, has been studied by quantum yield measurements and laser flash photolysis. The triplet-state lifetimes for all three molecules are long enough to give an isomerization pattern essentially determined by the thermodynamics of the triplet excited-state surface, that is, equilibration processes are much faster than decay processes. Decay from the triplet excited-state surface occurs to various degrees from two equilibrated states, the planar 3E,E* and another with one double bond twisted, 3E,p*. Extension of pi-conjugation gives more 2-fold cis-trans isomerization, from the Z,Z isomer to the E,E isomer, due to aa more facile adiabatic than diabatic pathway for the isomerization reaction. For one of the molecules, 9,10-bisstyrylanthracene, 3, the Z,Z isomer undergoes exclusively 2-fold isomerization to yield the E,E isomer. 1,4-Bis(3,5-di-tert-butylstyryl)naphthalene, 2, shows mainly 2-fold isomerization from the Z,Z isomer, but there is also a diabatic contribution to this isomerization giving a photostationary state, ZE:EE, 18:82. For 4,4'-bis(3,5-di-tert-butylstyryl)biphenyl, 1, the isomerization is still partly adiabatic. There is no decay from the 3Z,p* but all decay occurs from 3E,p*, giving a photostationary state ZE:EE, ca. 50:50. The photostationary states for the bisstyrylnaphthalene and the bisstyrylbiphenyl can be affected by the addition of aa triplet quencher, azulene or perylene, to give almost pure E,E.

  DOI：

  10.1021/j100196a034