1-hexyl-2-vinyl-1H-pyrrole | 1296085-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-hexyl-2-vinyl-1H-pyrrole
• 英文别名: 2-ethenyl-1-hexylpyrrole
• CAS: 1296085-23-8
• 化学式: C₁₂H₁₉N
• 分子量: 177.29
• InChiKey: NDUXGMCHDSEZPH-UHFFFAOYSA-N

物化性质

• 沸点：
  263.4±9.0 °C(Predicted)
• 密度：
  0.85±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-hexyl-2-vinyl-1H-pyrrole 、 5,8-dibromo-2,3-bis(4-trifluoromethylphenyl)pyrido[3,4-b]pyrazine 、 N,N-二甲基甲酰胺 在 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 、 lithium chloride 作用下， 反应 24.5h， 以26%的产率得到5,8-bis((E)-2-(1-hexyl-1H-pyrrol-2-yl)vinyl)-2,3-bis(4-(trifluoromethyl)phenyl)pyrido[3,4-b]pyrazine
  参考文献：
  名称：

  A Low-Bandgap Conjugated Polymer Based on Squaraine with Strong Two-Photon Absorption

  摘要：

  A new low-bandgap pi-conjugated D-A copolymer of squaraine and pyridopyrazine (P1) and a new small molecule squaraine-pyridopyrazine model compound (P2) were synthesized and compared. PI and P2 exhibit strong NIR absorption and low bandgap (1-1.3 eV). P2 in solution shows an intense and sharp absorption peak at 764 nm, while P1 in solution exhibits a red-shifted and broad absorption peak at 808 nm. The HOMO and LUMO levels of P1 were estimated to be -5.02 and -4.15 eV, while the HOMO and LUMO levels of P2 were estimated to be -5.27 and -3.22 eV, respectively. Polymer PI exhibits strong two-photon absorption (2PA) at telecommunication wavelengths with 2PA cross sections per repeat unit as high as 2300 GM, 3-5 times that for the small molecule P2. The higher HOMO, the lower LUMO levels, lower bandgap, red-shifted absorption, and stronger two-photon absorption of PI are attributed to higher degree of conjugation and delocalization of pi-electrons in the polymer.

  DOI：

  10.1021/ma200386f
• 作为产物：
  描述：

  1-hexyl-1H-pyrrole-2-carbaldehyde 、 甲基三苯基溴化膦 在 sodium ethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以70%的产率得到1-hexyl-2-vinyl-1H-pyrrole
  参考文献：
  名称：

  A Low-Bandgap Conjugated Polymer Based on Squaraine with Strong Two-Photon Absorption

  摘要：

  A new low-bandgap pi-conjugated D-A copolymer of squaraine and pyridopyrazine (P1) and a new small molecule squaraine-pyridopyrazine model compound (P2) were synthesized and compared. PI and P2 exhibit strong NIR absorption and low bandgap (1-1.3 eV). P2 in solution shows an intense and sharp absorption peak at 764 nm, while P1 in solution exhibits a red-shifted and broad absorption peak at 808 nm. The HOMO and LUMO levels of P1 were estimated to be -5.02 and -4.15 eV, while the HOMO and LUMO levels of P2 were estimated to be -5.27 and -3.22 eV, respectively. Polymer PI exhibits strong two-photon absorption (2PA) at telecommunication wavelengths with 2PA cross sections per repeat unit as high as 2300 GM, 3-5 times that for the small molecule P2. The higher HOMO, the lower LUMO levels, lower bandgap, red-shifted absorption, and stronger two-photon absorption of PI are attributed to higher degree of conjugation and delocalization of pi-electrons in the polymer.

  DOI：

  10.1021/ma200386f