4-[4-(1,3-benzothiazol-2-yl)phenoxy]phthalonitrile | 1413131-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[4-(1,3-benzothiazol-2-yl)phenoxy]phthalonitrile
• 英文别名: 4-[4-(1,3-Benzothiazol-2-yl)phenoxy] phthalonitrile；4-[4-(1,3-benzothiazol-2-yl)phenoxy]benzene-1,2-dicarbonitrile
• CAS: 1413131-93-7
• 化学式: C₂₁H₁₁N₃OS
• 分子量: 353.404
• InChiKey: CXCVZPLIZJITGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(1,3-苯并噻唑-2-基)苯酚 、 4-硝基邻苯二甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 以86%的产率得到4-[4-(1,3-benzothiazol-2-yl)phenoxy]phthalonitrile
  参考文献：
  名称：

  Self-assembling novel phthalocyanines containing a rigid benzothiazole skeleton with a 1,4-benzene linker: Synthesis, spectroscopic and spectral properties, and photochemical/photophysical affinity

  摘要：

  A novel benzothiazole containing phthalonitrile derivative and its peripherally tetra substituted metal free (4), Ni(II) (5), Zn(II) (6), Cu(II) (7) and Ti(IV) (8) phthalocyanines have been synthesized. The novel compounds were characterized by elemental analysis. IR. UV-Vis, H-1 NMR, C-13 NMR and mass spectroscopy. Zn(II)Pc (6) showed monomeric behavior in THF up to 7 x 10(-5) mol dm(-3) concentration and in various solvents (pyridine, dichloromethane, DMF and DMSO) up to 4 x 10(-5) mol dm(-3) concentration. On the other hand, Cu(II)Pc (7) formed aggregates in THF at concentrations higher than 3.6 x 10(-5) mol dm(-3) and showed monomeric behavior in THF. DMF and DMSO at 2.4 x 10(-5) mol dm(-3). Furthermore, the photochemical and photophysical properties of the metal free (4), Zn(II) (6) and Ti(IV) (8) phthalocyanines were investigated in THF. All the investigated phthalocyanines showed similar fluorescence behavior in THF. The synthesized Ni(II) (5) and Cu(II) (7) phthalocyanines were not evaluated for this purpose because of the paramagnetic behavior of the central metals in the cavity of these complexes. Singlet oxygen generation properties of these phthalocyanine compounds were also investigated and the order of singlet oxygen quantum yields were found as: Zn(II) Pc (6) > Ti(IV) Pc (8) > unsubstituted Zn(II) Pc (ZnPc) > metal free Pc (4). The degradation of the studied compounds was studied under light irradiation and the oxotitanium (IV) phthalocyanine derivative was found to be very sensitive to light irradiation. The fluorescence quenching behavior of the studied novel peripherally tetra 4-(1,3-benzothiazol-2-yl)phenoxy substituted metal free (4), Zn(II) (6) and Ti(IV) (8) phthalocyanines by the addition of 1,4-benzoquinone was also studied. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.08.074