4-[2-[4-[2-[4-[2-[2,5-diethyl-4-(2-phenylethynyl)phenyl]ethynyl]-2,5-diethylphenyl]ethynyl]-2,5-diethylphenyl]ethynyl]-N,N-diphenylaniline | 1243693-89-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[2-[4-[2-[4-[2-[2,5-diethyl-4-(2-phenylethynyl)phenyl]ethynyl]-2,5-diethylphenyl]ethynyl]-2,5-diethylphenyl]ethynyl]-N,N-diphenylaniline
• CAS: 1243693-89-1
• 化学式: C₆₂H₅₅N
• 分子量: 814.125
• InChiKey: RTEGSDREKILPOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.13
• 重原子数：
  63.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-((4-((4-((2,5-diethyl-4-iodophenyl)ethynyl)-2,5-diethylphenyl)ethynyl)-2,5-diethylphenyl)ethynyl)-N,N-diphenylaniline 、 苯乙炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 甲苯 为溶剂， 以94%的产率得到4-[2-[4-[2-[4-[2-[2,5-diethyl-4-(2-phenylethynyl)phenyl]ethynyl]-2,5-diethylphenyl]ethynyl]-2,5-diethylphenyl]ethynyl]-N,N-diphenylaniline
  参考文献：
  名称：

  Synthesis and spectroscopic study of phenylene–(poly)ethynylenes substituted by amino or amino/cyano groups at terminal(s): electronic effect of cyano group on charge-transfer excitation of acetylenic π-systems

  摘要：

  To gain insight into substituent electronic effect on charge-transfer excitation of acetylenic pi-systems, phenylene-(poly)ethynylenes substituted by Ph2N or Ph2N/cyano groups were synthesized by combination of Sonogashira coupling and double elimination protocol of beta-substituted sulfones. These substituted phenyleneethynylenes showed large molar absorption coefficients epsilon, and emitted strong fluorescence upon UV light irradiation. Phenylene (poly)ethynylenes, which involve butadiyne or hexatriyne motifs, emitted fluorescence in remarkably lower fluorescence quantum yields Phi(F) as their polyethynylene motifs -(C C)(n)- expanded. The drastic decrease of fluorescence quantum yields Phi(F) were explained in terms of increasing nonradiative reaction rate constants k(nr), which had been determined by the corresponding fluorescence quantum yields Phi(F) and lifetime values tau. The emission underwent a large bathochromic shift in polar solvents because the charge-separated excited state is more stabilized than the ground state. Comparison of slope values rho in Lippert/Mataga plot for the Ph2N and Ph2N/cyano-substituted phenylene (poly)ethynylenes revealed that the latter underwent large change of dipole moments upon photo-excitation although highly expanded acetylenic pi-systems with cyano group did little. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.016

文献信息

• Synthesis and spectroscopic study of phenylene–(poly)ethynylenes substituted by amino or amino/cyano groups at terminal(s): electronic effect of cyano group on charge-transfer excitation of acetylenic π-systems
  作者：Jing-Kun Fang、De-Lie An、Kan Wakamatsu、Takeharu Ishikawa、Tetsuo Iwanaga、Shinji Toyota、Shin-ichi Akita、Daisuke Matsuo、Akihiro Orita、Junzo Otera

  DOI：10.1016/j.tet.2010.05.016

  日期：2010.7

  To gain insight into substituent electronic effect on charge-transfer excitation of acetylenic pi-systems, phenylene-(poly)ethynylenes substituted by Ph2N or Ph2N/cyano groups were synthesized by combination of Sonogashira coupling and double elimination protocol of beta-substituted sulfones. These substituted phenyleneethynylenes showed large molar absorption coefficients epsilon, and emitted strong fluorescence upon UV light irradiation. Phenylene (poly)ethynylenes, which involve butadiyne or hexatriyne motifs, emitted fluorescence in remarkably lower fluorescence quantum yields Phi(F) as their polyethynylene motifs -(C C)(n)- expanded. The drastic decrease of fluorescence quantum yields Phi(F) were explained in terms of increasing nonradiative reaction rate constants k(nr), which had been determined by the corresponding fluorescence quantum yields Phi(F) and lifetime values tau. The emission underwent a large bathochromic shift in polar solvents because the charge-separated excited state is more stabilized than the ground state. Comparison of slope values rho in Lippert/Mataga plot for the Ph2N and Ph2N/cyano-substituted phenylene (poly)ethynylenes revealed that the latter underwent large change of dipole moments upon photo-excitation although highly expanded acetylenic pi-systems with cyano group did little. (C) 2010 Elsevier Ltd. All rights reserved.