5-(4-iodophenyl)-N-[5-(4-iodophenyl)-3-phenyl-1H-pyrrol-2-yl]-3-phenylpyrrol-2-imine | 1256705-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 5-(4-iodophenyl)-N-[5-(4-iodophenyl)-3-phenyl-1H-pyrrol-2-yl]-3-phenylpyrrol-2-imine
• CAS: 1256705-52-8
• 化学式: C₃₂H₂₁I₂N₃
• 分子量: 701.348
• InChiKey: WGBNVSFMPLQTAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(4-iodophenyl)-N-[5-(4-iodophenyl)-3-phenyl-1H-pyrrol-2-yl]-3-phenylpyrrol-2-imine 在 N,N-二异丙基乙胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以52%的产率得到5,5-difluoro-3,7-bis(4-iodophenyl)-1,9-diphenyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,5,2]triazaborinin-4-ium
  参考文献：
  名称：

  Near-Infrared Nitrofluorene Substitued Aza-Boron-dipyrromethenes Dyes

  摘要：

  The synthesis, spectroscopic properties, and TD-DFT calculations of new aza-Boron-dipyromethene dyes featuring pendant nitrofluorenylethynyl substituents are described. This functionalization allows for moving the luminescence in the NIR, conserving a good quantum yield efficiency.

  DOI：

  10.1021/ol102701v
• 作为产物：
  描述：

  ω-Benzyliden-4-iodacetophenon 在 ammonium acetate 、 二乙胺 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 76.0h， 生成 5-(4-iodophenyl)-N-[5-(4-iodophenyl)-3-phenyl-1H-pyrrol-2-yl]-3-phenylpyrrol-2-imine
  参考文献：
  名称：

  Near-Infrared Nitrofluorene Substitued Aza-Boron-dipyrromethenes Dyes

  摘要：

  The synthesis, spectroscopic properties, and TD-DFT calculations of new aza-Boron-dipyromethene dyes featuring pendant nitrofluorenylethynyl substituents are described. This functionalization allows for moving the luminescence in the NIR, conserving a good quantum yield efficiency.

  DOI：

  10.1021/ol102701v

文献信息

• Highly near-infrared photoluminescence from aza-borondipyrromethene-based conjugated polymers
  作者：Ryousuke Yoshii、Atsushi Nagai、Yoshiki Chujo

  DOI：10.1002/pola.24335

  日期：2010.12.1

  AbstractNear‐infrared (NIR) emissive conjugated polymers were prepared by palladium‐catalyzed Sonogashira polymerization of diiodobenzene‐functionalized aza‐borondipyrromethene (Aza‐BODIPY) monomers, which were substituted at 3 and 5 or 1 and 7 positions on the Aza‐BODIPY core, with 1,4‐diethynyl‐2,5‐dihexadecyloxybenzene or 3,3′‐didodecyl‐2,2′‐diethynyl‐5,5′‐bithiophene. The structures of the polymers were confirmed by 1H NMR, 13C NMR, 11B NMR, Fourier transform infrared (FT‐IR) spectroscopies, and size exclusion chromatography (SEC). The optical properties were then characterized by UV–vis absorption and photoluminescence (PL) spectroscopies, and theoretical calculation using density‐functional theory (DFT) method. The polymers were fusible and soluble in common organic solvents including tetrahydrofuran (THF), o‐xylene, toluene, CHCl3, and CH2Cl2, etc. The UV–vis absorption and PL spectra of the polymers shifted to long wavelength region in comparison with simple Aza‐BODIPY as the counterpart because of extended π‐conjugation of the polymers. The polymers efficiently emitted NIR light with narrow emission bands at 713∼777 nm on excitation at each absorption maximum. Especially, the polymer attached 1,4‐diethynyl‐2,5‐dihexadecyloxybenzene to 3,5‐position on the core revealed intense quantum yields (ϕF = 24%) in this NIR region (753 nm). © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010