1,4-dibromo-2,5-bis[(4'-nitro-2'-((triisopropylsilyl)ethynyl)phenyl)ethynyl]benzene | 834856-10-9

• 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: 1,4-dibromo-2,5-bis[(4'-nitro-2'-((triisopropylsilyl)ethynyl)phenyl)ethynyl]benzene
• CAS: 834856-10-9
• 化学式: C₄₄H₅₀Br₂N₂O₄Si₂
• 分子量: 886.871
• InChiKey: YSKZPDMXHWLLKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.97
• 重原子数：
  54.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N-dibutyl-4-ethynyl-3-[(triisopropylsilyl)ethynyl]aniline 、 1,4-dibromo-2,5-bis[(4'-nitro-2'-((triisopropylsilyl)ethynyl)phenyl)ethynyl]benzene 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以87%的产率得到1,4-bis[(4'-N,N-dibutylamino-2'-((triisopropylsilyl)ethynyl)phenyl)ethynyl]-2,5-bis[(4''-nitro-2''-((triisopropylsilyl)ethynyl)phenyl)ethynyl]benzene
  参考文献：
  名称：

  Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes

  摘要：

  A series of tetrakis(phenylethynyl)benzenes and bis(dehydrobenzoannuleno)benzenes have been synthesized containing tetra-substitutions of neutral, donor, and mixed donor/acceptor groups. To ascertain the importance of substitutional and structural differences of the phenylacetylenes, the optical absorption and emission properties of each series were examined. Conjugation effectiveness, electron density, planarity, and geometry of charge-transfer pathways were found to have a pronounced effect on the overall optical and material properties. Considerable self-association behavior due to face-to-face stacking in solution was observed for donor/acceptor-functionalized macrocycles and was quantified by concentration-dependent H-1 NMR measurements. A solvent-dependent polymerization of one macrocycle regioisomer was observed and characterized. To provide further insight into the energy levels and electronic transitions present, computational studies of each system were performed.

  DOI：

  10.1021/ja044175a
• 作为产物：
  描述：

  5-nitro-1-[(triisopropylsilyl)ethynyl]-2-[(trimethylsilyl)ethynyl]benzene 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.0h， 生成 1,4-dibromo-2,5-bis[(4'-nitro-2'-((triisopropylsilyl)ethynyl)phenyl)ethynyl]benzene
  参考文献：
  名称：

  Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes

  摘要：

  A series of tetrakis(phenylethynyl)benzenes and bis(dehydrobenzoannuleno)benzenes have been synthesized containing tetra-substitutions of neutral, donor, and mixed donor/acceptor groups. To ascertain the importance of substitutional and structural differences of the phenylacetylenes, the optical absorption and emission properties of each series were examined. Conjugation effectiveness, electron density, planarity, and geometry of charge-transfer pathways were found to have a pronounced effect on the overall optical and material properties. Considerable self-association behavior due to face-to-face stacking in solution was observed for donor/acceptor-functionalized macrocycles and was quantified by concentration-dependent H-1 NMR measurements. A solvent-dependent polymerization of one macrocycle regioisomer was observed and characterized. To provide further insight into the energy levels and electronic transitions present, computational studies of each system were performed.

  DOI：

  10.1021/ja044175a