(4-Butylphenyl)-[2,5-dibromo-4-(4-butylbenzoyl)thiophen-3-yl]methanone | 197370-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-Butylphenyl)-[2,5-dibromo-4-(4-butylbenzoyl)thiophen-3-yl]methanone
• CAS: 197370-02-8
• 化学式: C₂₆H₂₆Br₂O₂S
• 分子量: 562.365
• InChiKey: NPCAXFGMEZCQAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  641.6±55.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-Butylphenyl)-[2,5-dibromo-4-(4-butylbenzoyl)thiophen-3-yl]methanone 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Imine-Bridged Planar Poly(phenylenethiophene)s and Polythiophenes

  摘要：

  Synthetic routes to soluble planar poly(phenylenethiophene)s and polythiophenes are described. The main polymer backbones are synthesized via Pd(0)-catalyzed couplings of the electron-rich N,N'-(bis-tert-butoxycarbonyl)-3,4-diamino-2,5-bis(tri-n-butylstannyl)thiophene with electron-deficient aryldibromodiones. The prebridged polymers have bathochromically shifted absorptions due to donor/acceptor interactions between the consecutive repeat units. Upon exposure of the polymers to trifluoroacetic acid or titanium tetrachloride, imine bridges are formed that force the consecutive units into planarity. The bridging units are sp(2)-hybridized, thus allowing for greater electron delocalization between the consecutive aryl units. The syntheses of model trimeric systems were conducted to provide further data for assessing the optical properties of the polymers. Protonation of the imine moieties causes bathochromic shifts of >100 nm in several cases. The effect is explained by an intramolecular charge transfer. Thus these arrangements of planar structures with imine bridges serve as optically based proton sensors with spectral shift differences far-exceeding those of nonplanar imine-containing polymers.

  DOI：

  10.1021/ja964223u
• 作为产物：
  描述：

  2,5-二溴-噻吩-3,4-二羧酸 在 三氯化铝 、 草酰氯 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.67h， 生成 (4-Butylphenyl)-[2,5-dibromo-4-(4-butylbenzoyl)thiophen-3-yl]methanone
  参考文献：
  名称：

  Imine-Bridged Planar Poly(phenylenethiophene)s and Polythiophenes

  摘要：

  Synthetic routes to soluble planar poly(phenylenethiophene)s and polythiophenes are described. The main polymer backbones are synthesized via Pd(0)-catalyzed couplings of the electron-rich N,N'-(bis-tert-butoxycarbonyl)-3,4-diamino-2,5-bis(tri-n-butylstannyl)thiophene with electron-deficient aryldibromodiones. The prebridged polymers have bathochromically shifted absorptions due to donor/acceptor interactions between the consecutive repeat units. Upon exposure of the polymers to trifluoroacetic acid or titanium tetrachloride, imine bridges are formed that force the consecutive units into planarity. The bridging units are sp(2)-hybridized, thus allowing for greater electron delocalization between the consecutive aryl units. The syntheses of model trimeric systems were conducted to provide further data for assessing the optical properties of the polymers. Protonation of the imine moieties causes bathochromic shifts of >100 nm in several cases. The effect is explained by an intramolecular charge transfer. Thus these arrangements of planar structures with imine bridges serve as optically based proton sensors with spectral shift differences far-exceeding those of nonplanar imine-containing polymers.

  DOI：

  10.1021/ja964223u

文献信息

• Zhang, Qing T.; Tour, James M., Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5355 - 5360
  作者：Zhang, Qing T.、Tour, James M.

  DOI：——

  日期：——