7-phenyl-1,2-dicyanonaphthalene | 134030-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-phenyl-1,2-dicyanonaphthalene
• 英文别名: 7-Phenylnaphthalene-1,2-dicarbonitrile
• CAS: 134030-38-9
• 化学式: C₁₈H₁₀N₂
• 分子量: 254.291
• InChiKey: UXSXFGSHPJVVIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-phenyl-1,2-dicyanonaphthalene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 五羰基铁 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Synthesis and characterization of substituted (1,2-naphthalocyaninato)iron compounds and bisaxially coordinated isocyanide complexes

  摘要：

  Tetrasubstituted (1,2-naphthalocyaninato)iron(II) compounds t-Bu4-1,2-NcFe (13), Me4-1,2-NcFe (14), and Ph4-1,2-NcFe (15) are obtained from 7-substituted 1,2-dicyanonaphthalenes 12a-c either by reaction with pentacarbonyliron in 1-chloronapthalene (method a) or with iron(II) acetate in 1-hexanol (method b), respectively. Compounds 13-15 were characterized by UV/vis, IR, and Mossbauer spectroscopy, and the oxidation potentials, measured by cyclic voltammetry in pyridine, are compared with the oxidation potentials of 1,2-NcFe and PcFe. The substituted (1,2-naphthalocyaninato)iron compounds 13, 14, and 15 react with alkyl and aryl isocyanides R'NC (R' = t-Bu, c-Hx, Bz, Me2Ph), yielding the bisaxially coordinated isocyanide complexes of 13, 14, and 15, R4-1,2-NcFe (R'NC)2. Due to their comparatively high solubility in organic solvents, it is possible to characterize the isocyanide complexes with H-1 and C-13 NMR spectroscopy. The H-1 NMR spectra of, for example, t-Bu4-1,2-NcFe(t-BuNC)2 reveal that only one of the structural isomers of the unsymmetrical 1,2-naphthalocyanine macrocycle, namely, the 1,2-naphthalocyanine with C4h symmetry (see Figure 1) is formed, if the synthesis starting with 7-tert-butyl-1,2-dicyanonaphthalene (12a) is carried out according to method a. The crystal structure of the isomer obtained, t-Bu4-1,2-Nc(t-BuNC)2, is determined (Figure 4) and confirms these findings. All isocyanide complexes R4-1,2-NcFe(R'NC)2 are characterized by spectral data and thermoanalyses. The reaction of R4-1,2-NcFe 13, 14, and 15 with diisocyanobenzene (dib) leads to the bridged compounds [R4-1,2-NcFe(dib)]n, R = t-Bu, Me, Ph. After being doped with iodine, the bridged complexes exhibit good semiconducting properties.

  DOI：

  10.1021/jo00011a012