4-[2-[3-(2-phenylethynyl)phenyl]ethynyl]benzonitrile | 1151549-78-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-[2-[3-(2-phenylethynyl)phenyl]ethynyl]benzonitrile
• CAS: 1151549-78-8
• 化学式: C₂₃H₁₃N
• 分子量: 303.363
• InChiKey: MVPLTXRFFYDXKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-溴-3-(苯基乙炔基)苯 、 4-乙炔基苯甲腈 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三叔丁基膦 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以32%的产率得到4-[2-[3-(2-phenylethynyl)phenyl]ethynyl]benzonitrile
  参考文献：
  名称：

  Emission from Regioisomeric Bis(phenylethynyl)benzenes during Pulse Radiolysis

  摘要：

  Emission from charge recombination between radical cations and anions of a series of regioisomeric 1,4-, 1,3-, and 1,2-bis(phenylethynyl)benzenes (bPEBs) substituted by various electron donor and/or acceptor groups was measured during pulse radiolysis in benzene (Bz). The formation of bPEB in the excited singlet state ((1)bPEB*) can be attributed to the charge recombination between bPEB(center dot+) and bPEB(center dot-), which are initially generated from the radiolytic reaction. This mechanism is reasonably explained by the relationship between the annihilation enthalpy change (-Delta H degrees) for the charge recombination of bPEB(center dot+) and bPEB(center dot-) and excitation energy of (1)bPEB*. Since the degree of the pi-conjugation in the S-1 state and HOMO-LUMO levels of bPEB change with the substitution pattern of phenylacetylene groups on the central benzene ring and the various kinds of donor and/or acceptor group, the fine-tuning of the emission color and intensity of bPEB can be easily carried out during pulse radiolysis in Bz. For donor-acceptor-substituted bPEB, it was found that the difference in the charge transfer conjugated pathways between donor and acceptor substituents (linear-, cross-, and "bent"-conjugated pathways) strongly influenced the HOMO-LUMO energy gap.

  DOI：

  10.1021/jo900494j

文献信息

• Emission from Regioisomeric Bis(phenylethynyl)benzenes during Pulse Radiolysis
  作者：Shingo Samori、Sachiko Tojo、Mamoru Fujitsuka、Torben Ryhding、Aaron G. Fix、Brittany M. Armstrong、Michael M. Haley、Tetsuro Majima

  DOI：10.1021/jo900494j

  日期：2009.5.15

  Emission from charge recombination between radical cations and anions of a series of regioisomeric 1,4-, 1,3-, and 1,2-bis(phenylethynyl)benzenes (bPEBs) substituted by various electron donor and/or acceptor groups was measured during pulse radiolysis in benzene (Bz). The formation of bPEB in the excited singlet state ((1)bPEB*) can be attributed to the charge recombination between bPEB(center dot+) and bPEB(center dot-), which are initially generated from the radiolytic reaction. This mechanism is reasonably explained by the relationship between the annihilation enthalpy change (-Delta H degrees) for the charge recombination of bPEB(center dot+) and bPEB(center dot-) and excitation energy of (1)bPEB*. Since the degree of the pi-conjugation in the S-1 state and HOMO-LUMO levels of bPEB change with the substitution pattern of phenylacetylene groups on the central benzene ring and the various kinds of donor and/or acceptor group, the fine-tuning of the emission color and intensity of bPEB can be easily carried out during pulse radiolysis in Bz. For donor-acceptor-substituted bPEB, it was found that the difference in the charge transfer conjugated pathways between donor and acceptor substituents (linear-, cross-, and "bent"-conjugated pathways) strongly influenced the HOMO-LUMO energy gap.