3-(8'-hydroxy-1,1'-binaphthyl-8-yloxy)phthalonitrile | 1257339-75-5

• 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: 3-(8'-hydroxy-1,1'-binaphthyl-8-yloxy)phthalonitrile
• CAS: 1257339-75-5
• 化学式: C₂₈H₁₆N₂O₂
• 分子量: 412.447
• InChiKey: RNJLUMXLVSRQQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  60 °C(Solvent: Ethanol)
• 沸点：
  652.4±55.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.04
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-硝基邻苯二腈 、 1,1'-binaphthalene-8,8'-diol 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以40%的产率得到3-(8'-hydroxy-1,1'-binaphthyl-8-yloxy)phthalonitrile
  参考文献：
  名称：

  Synthesis and photophysical properties of 1,1′-binaphthol substituted phthalocyanines

  摘要：

  We report on the synthesis, characterization and photophysical properties of a new symmetrically tetra substituted {at non-peripheral positions with tetra(1,1'-bi-binaphtoxy)} phthalocyanines containing H-2, Mg(II), Al(III) Cl, Si(IV)Cl-2 in the central cavity. The synthesized compounds were characterized by the elemental analyses, UV-Vis, FT-IR and H-1 NMR spectroscopies. The fluorescence quantum yields, triplet quantum yields and lifetimes of the newly synthesized H-2, Mg, Al, and Si phthalocyanines were explored. Triplet quantum yields ranged from 0.24 to 0.54. The triplet lifetime for the silicon phthalocyanine derivative was the highest ever reported for a phthalocyanine (similar to 3.5 ms). (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.06.034

文献信息

• Syntheses, electrochemical and spectroelectrochemical properties of novel ball-type and mononuclear Co(II) phthalocyanines substituted at the peripheral and non-peripheral positions with binaphthol groups
  作者：Mevlüde Canlıca、Irvin Noel Booysen、Tebello Nyokong

  DOI：10.1016/j.poly.2010.11.017

  日期：2011.2

  Mononuclear cobalt phthalocyanine (CoPc) substituted at the non-peripheral Sand peripheral positions 9 with 1,1'-binaphthy1-8,8'-diol and ball-type dinuclear Co2Pc2 substituted at the non-peripheral 10 and peripheral 11 positions with the same substituent are reported. The complexes with 1,1'-binaphthol-bridges were prepared from the corresponding phthalonitriles 4-7. The effects of the position of substituent on spectral, electrochemical and spectroelectrochemical properties of these complexes were also explored. The mononuclear complexes 8 and 9 exhibited one metal reduction, one ring reduction and one ring oxidation. The redox properties of the ball-type complexes 10 and 11 exhibited two reduction processes assigned to [((CoPc-2)-Pc-I)(2)](2-)/[((CoPc-3)-Pc-I)(2)](4-) (I), ((COPc-2)-Pc-II)(2)/[((COPc-2)-Pc-I)(2)](2-) (II) and one oxidation process assigned to [((CoPc-2)-Pc-III)(2)](2+)/(CoPc-2)-Pc-II)(2) (III). The ball-type complexes are much easier to oxidize and more difficult to reduce than the corresponding monomers 8 and 9. (C) 2010 Elsevier Ltd. All rights reserved.