4-hydroxylphenoxyphthalonitrile | 1159585-13-3

• 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-hydroxylphenoxyphthalonitrile
• 英文别名: 3-(4-hydroxyphenoxy)phthalonitrile；3-(p-hydroxylphenoxy)phthalonitrile；3-(4-hydroxyphenoxy)benzene-1,2-dicarbonitrile
• CAS: 1159585-13-3
• 化学式: C₁₄H₈N₂O₂
• 分子量: 236.23
• InChiKey: SVXGYYYWJCMVFE-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C(Solvent: Ethanol)
• 沸点：
  450.6±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxylphenoxyphthalonitrile 在 zinc diacetate 、 lithium 作用下， 以 戊醇 为溶剂， 反应 1.0h， 以30%的产率得到tetra[α-(4-hydroxyphenoxy)] zinc phthalocyanine
  参考文献：
  名称：

  通过光诱导分子内电子转移和 pH 值调节的苯酚改性锌酞菁的荧光特性

  摘要：

  合成了四[α-(4-羟基苯氧基)]锌酞菁，ZnPc(α-OPhOH) 4，并发现其光物理特性与pH值有很大关系。当它溶解在碱性溶液中时，观察到大约 700 nm 的双荧光发射。酞菁的荧光可以在pH 9.1急剧关闭因的ZnPc（α-OPhONa）分子内光诱导电子转移（PET）4，通过的ZnPc（α-OPhOH）的去质子化形成4。ZnPc(α-OPhOH) 4和ZnPc(α-OPhONa) 4的光物理通过紫外-可见吸收、稳态和时间分辨荧光以及瞬态吸收(TA)进行了详细研究，以揭示荧光猝灭机制。ZnPc(α-OPhONa) 中的分子内 PET4从供体 PhONa 亚基到受体 ZnPc 部分的特征在于更小的荧光量子产率 (0.003) 和寿命 (<0.20 ns)。PET 进一步由 TA 光谱中电荷分离态 (CSS) 的出现证明，即由 ZnPc 的阴离子自由基和苯酚自由基引起的带。电荷分离态的寿命约为。3

  DOI：

  10.1007/s10895-011-0844-0
• 作为产物：
  描述：

  3-(4-methoxy-phenoxy)phthalonitrile 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到4-hydroxylphenoxyphthalonitrile
  参考文献：
  名称：

  Cobaltacarborane–phthalocyanine conjugates: Syntheses and photophysical properties

  摘要：

  Syntheses of two new cobaltacarborane-phthalocyanine conjugates, one anionic (Pc 6) and one zwitterionic (Pc 7), were accomplished via cyclotetramerization of the corresponding cobaltacarborane-substituted phthalonitriles (4 or 5) with excess phthalonitrile in quinoline. X-ray structures of two phthalonitrile precursors (2 and 3) were obtained and are discussed, and the absorption and emission properties of the two cobaltacarborane-phthalocyanine conjugates in several solvents were investigated. The anionic conjugate 6 exists mainly as a monomer in polar organic solvents and has fluorescence quantum yields in the region 0.2-0.3. The zwitterionic conjugate 7 aggregates in solution and displays lower quantum yields similar to 0.1 in organic solvents. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.11.037

文献信息

• Intramolecular aggregation and optical limiting properties of triazine-linked mono-, bis- and tris-phthalocyanines
  作者：Jun Chen、Tao Zhang、Shuangqing Wang、Rui Hu、Shayu Li、Jin Shi Ma、Guoqiang Yang

  DOI：10.1016/j.saa.2015.04.093

  日期：2015.10

  A series of triazine-linked mono-, bis- and tris-phthalocyanines are synthesized, intramolecular aggregation is found in bis- and tris-phthalocyanines via pi-pi stacking interaction. Theoretical and experimental studies reveal the formation of the intramolecular aggregation. The spectrographic, photophysical and nonlinear optical properties of these compounds are adjusted for the formation of the intramolecular aggregation. The bis-phthalocyanine dimer presents smaller fluorescence quantum yield, lower triplet formation yield and the triplet-minus-ground state extinction coefficient, which causes poorer optical limiting performance. It is interesting that the tris-phthalocyanine is composed of a mono-phthalocyanine part and a bis-phthalocyanine part, the optical limiting property of the tris-phthalocyanine is similar to that of mono-phthalocyanine. (C) 2015 Elsevier B.V. All rights reserved.