5-(4-methoxystyryl)isophthalaldehyde

• 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-(4-methoxystyryl)isophthalaldehyde
• 英文别名: 5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene-1,3-dicarbaldehyde
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: PEXSXFGCUHCZQY-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-methoxystyryl)isophthalaldehyde 以 乙醇 、 溶剂黄146 为溶剂， 反应 49.5h， 生成 E-[4-(4-methoxystyryl)-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：

  1,3,5-三(溴甲基)苯 在 sodium hydroxide 、 potassium tert-butylate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 5-(4-methoxystyryl)isophthalaldehyde
  参考文献：
  名称：

  偶极和非偶极聚（亚苯基亚乙烯基）树状聚合物的合成，表征和光学响应。

  摘要：

  使用Heck和Horner-Wadsworth-Emmons反应已有效地合成了带有供电子基团和吸电子基团的新型偶极和非偶极聚（亚苯基亚乙烯基）树状聚合物。这些系统的光致发光可通过选择适当的外围基团在蓝色区域进行调节。尽管有亚取代模式，但当pi供体基团和pi受体基团通过间亚苯基亚乙烯基系统连接时，仍可观察到较大的斯托克斯位移。

  DOI：

  10.1021/jo015764r

文献信息

• Syntheses, Structures, and Electronic and Optical Properties of Platinum(II) Complexes of 1,3-Bis(imino)benzene-Derived Pincer Ligands
  作者：Octavia A. Blackburn、Benjamin J. Coe、Madeleine Helliwell、James Raftery

  DOI：10.1021/om3003152

  日期：2012.8.13

  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.
• Synthesis, Characterization, and Optical Response of Dipolar and Non-Dipolar Poly(phenylenevinylene) Dendrimers
  作者：Enrique Díez-Barra、Joaquín C. García-Martínez、Sonia Merino、Riánsares del Rey、Julián Rodríguez-López、Prado Sánchez-Verdú、Juan Tejeda

  DOI：10.1021/jo015764r

  日期：2001.8.1

  New dipolar and non-dipolar poly(phenylenevinylene) dendrimers bearing electron-donating and electron-withdrawing groups have been efficiently synthesized using Heck and Horner-Wadsworth-Emmons reactions. The photoluminescence of these systems may be tuned in the blue zone by choosing the appropriate peripheral groups. Despite the meta-substitution pattern, large Stokes shifts can be observed when

  使用Heck和Horner-Wadsworth-Emmons反应已有效地合成了带有供电子基团和吸电子基团的新型偶极和非偶极聚（亚苯基亚乙烯基）树状聚合物。这些系统的光致发光可通过选择适当的外围基团在蓝色区域进行调节。尽管有亚取代模式，但当pi供体基团和pi受体基团通过间亚苯基亚乙烯基系统连接时，仍可观察到较大的斯托克斯位移。