5-styrylisophthalaldehyde | 1391132-81-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5-styrylisophthalaldehyde
• CAS: 1391132-81-2
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: IMBCQJSZAUZRLU-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-styrylisophthalaldehyde 以 氘代氯仿 、 乙醇 、 溶剂黄146 为溶剂， 反应 49.5h， 生成 Z-[4-styryl-2,6-bis(N-methylimino)phenyl]chloroplatinum
  参考文献：
  名称：

  Syntheses, Structures, and Electronic and Optical Properties of Platinum(II) Complexes of 1,3-Bis(imino)benzene-Derived Pincer Ligands

  摘要：

  Six new Pt-II complexes of 5-substituted 1,3-bis(N-methylimino)benzene (bIBH)-derived ligands have been synthesized by direct reactions with (K2PtCl4)-Cl-II in glacial acetic acid. The ethenylene groups in the two styryl-substituted complexes undergo E-Z photoisomerization, as revealed by H-1 NMR spectroscopy. The UV-vis spectra of the styryl-/aryl-substituted complexes show intense high-energy bands due to ligand-based pi -> pi* transitions and a number of weaker bands at lower energies in the 300-500 nm region. Time-dependent density functional theory (TD-DFT) calculations indicate that the latter absorptions have mixed intraligand pi -> pi* and Pt(d) -> pi* metal-to-ligand charge-transfer (MLCT) character. Four of the new complexes give vibronically structured emission profiles in fluid solution at room temperature. The luminescence quantum yields and lifetimes in nondegassed dichloromethane are in the ranges 0.1-0.2% and 159-170 ns, respectively. In contrast, the styryl-substituted complexes are nonemissive, due to excited-state quenching by E -> Z isomerization. DFT indicates that the emissive triplet state has mixed ligand-to-ligand charge-transfer and MLCT character, with a geometry distorted with respect to the symmetric ground state. Single-crystal X-ray structures have been determined for two of the complexes, showing N-Pt-N angles of ca. 159 degrees. The complex of an unsubstituted bIB(-) ligand is deep red and forms columns with short Pt center dot center dot center dot Pt distances of ca. 3.55 angstrom, indicating weak intermetallic interactions.

  DOI：

  10.1021/om3003152
• 作为产物：
  描述：

  间苯二甲醛 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 作用下， 以 硫酸 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 5-styrylisophthalaldehyde
  参考文献：
  名称：

  Syntheses, Structures, and Electronic and Optical Properties of Platinum(II) Complexes of 1,3-Bis(imino)benzene-Derived Pincer Ligands

  摘要：

  Six new Pt-II complexes of 5-substituted 1,3-bis(N-methylimino)benzene (bIBH)-derived ligands have been synthesized by direct reactions with (K2PtCl4)-Cl-II in glacial acetic acid. The ethenylene groups in the two styryl-substituted complexes undergo E-Z photoisomerization, as revealed by H-1 NMR spectroscopy. The UV-vis spectra of the styryl-/aryl-substituted complexes show intense high-energy bands due to ligand-based pi -> pi* transitions and a number of weaker bands at lower energies in the 300-500 nm region. Time-dependent density functional theory (TD-DFT) calculations indicate that the latter absorptions have mixed intraligand pi -> pi* and Pt(d) -> pi* metal-to-ligand charge-transfer (MLCT) character. Four of the new complexes give vibronically structured emission profiles in fluid solution at room temperature. The luminescence quantum yields and lifetimes in nondegassed dichloromethane are in the ranges 0.1-0.2% and 159-170 ns, respectively. In contrast, the styryl-substituted complexes are nonemissive, due to excited-state quenching by E -> Z isomerization. DFT indicates that the emissive triplet state has mixed ligand-to-ligand charge-transfer and MLCT character, with a geometry distorted with respect to the symmetric ground state. Single-crystal X-ray structures have been determined for two of the complexes, showing N-Pt-N angles of ca. 159 degrees. The complex of an unsubstituted bIB(-) ligand is deep red and forms columns with short Pt center dot center dot center dot Pt distances of ca. 3.55 angstrom, indicating weak intermetallic interactions.

  DOI：

  10.1021/om3003152