4-(2-pyridyloxy)phthalonitrile | 185388-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-pyridyloxy)phthalonitrile
• 英文别名: 4-pyridin-2-yloxybenzene-1,2-dicarbonitrile
• CAS: 185388-52-7
• 化学式: C₁₃H₇N₃O
• 分子量: 221.218
• InChiKey: IVJXGJFQPLNKAT-UHFFFAOYSA-N

物化性质

• 沸点：
  427.4±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.7
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(2-pyridyloxy)phthalonitrile 、 mercury dichloride 在 1,8-diazabicyclo[5.4.0]undec-7-ene 作用下， 以 戊醇 为溶剂， 以41%的产率得到Hg[(2-NO2C6H4)2triazenido]2
  参考文献：
  名称：

  锌，镉和汞的新型酞菁衍生物的合成与光物理

  摘要：

  提出了锌，镉和汞（TPyZnPc，TPyCdPc和TPyHgPc）的新型四{2，（3）-吡啶氧基邻苯二甲酰氰基}络合物的合成。研究了它们的光谱和光物理性质（以及未取代的对应物：ZnPc，CdPc和HgPc）。TPyZnPc和TPyCdPc聚集在非配位溶剂（如氯仿）中，而TPyHgPc则被脱金属，这从它们各自的吸收光谱可以明显看出。荧光的趋势（Φ ˚F），三重峰（Φ Ť）和单线态氧（Φ Δ）量子产率在自旋-轨道的相对强度的术语解释耦合感应通过在复合物中的各自的中心金属离子。吡啶氧基取代基的作用是降低Φ ˚F和增加Φ Ť值。该配合物是在DMSO中较少的荧光，但具有较高的Φ Ť，三线态寿命（τ Ť）和Φ Δ在其中。

  DOI：

  10.1039/b615663k
• 作为产物：
  描述：

  2-羟基吡啶 、 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， 生成 4-(2-pyridyloxy)phthalonitrile
  参考文献：
  名称：

  水溶性四磺化，八羧化和季铵化2，（3）-四-（2吡啶氧基）Ga酞菁的合成及光物理性质

  摘要：

  比较了氯镓2，（3）-四-（2吡啶氧基）酞菁（ClGaT-2-PyPc）及其季铵化衍生物与水溶性阴离子四磺化镓酞菁（（OH）GaTSPc）和羟基镓的光物理行为八羧基酞菁（（OH）GaOCPc）。尽管季铵化的化合物和四磺化镓酞菁都在水溶液中聚集。表面活性剂Cremophore EL的存在下，在pH为11的溶液中导致荧光和三重态收率低提高产量。三重态量子产率范围为0.52至0.70，荧光量子产率范围为<0.01至0.21。取代基的性质（磺酸盐，羧基和吡啶氧基）不影响光物理性质。在DMSO和水溶液中，与四磺化镓酞菁（（OH）GaTSPc）和羟基镓八羧基酞菁相比，Chlorogallium 2，（3）-tetra-（2pyridiloxy）酞菁及其季铵化衍生物具有更长的三重态寿命。在表面活性剂存在和不存在的情况下都可以使用介质。

  DOI：

  10.1016/j.dyepig.2009.09.011

文献信息

• Photophysical properties of pyridyloxy phthalocyanine encapsulated in nanoparticles
  作者：Kuizhi Chen、Di Zeng、Ying Huang、Yawen Chen、Yide Huang、Shusen Xie、Yiru Peng、Qing Ye

  DOI：10.1080/00387010.2018.1461654

  日期：2018.7.3

  a cosolvent method. The morphologies and photophysical properties of phthalocyanines encapsulated in nanoparticles were studied by transmission electron microscope, ultraviolet-visible, and fluorescence spectroscopic methods. The photophysical properties of phthalocyanines encapsulated into nanoparticles exhibited substitution positions dependence. The phthalocyanines with substitution at α positions

  摘要 合成了两种α/β位被吡啶氧基取代的氯化铝酞菁。通过红外光谱、质子核磁共振和元素分析对其结构进行了表征。通过共溶剂法将四-α(β)-(2-吡啶氧基)氯化铝酞菁封装到二嵌段共聚物甲氧基-聚(乙二醇)-嵌段-聚(L-赖氨酸)中。通过透射电子显微镜、紫外-可见光和荧光光谱方法研究了封装在纳米颗粒中的酞菁的形貌和光物理性质。封装在纳米颗粒中的酞菁的光物理特性表现出取代位置依赖性。
• Physico-chemical properties of lutetium phthalocyanine complexes in solution and in solid polystyrene polymer fibers and their application in photoconversion of 4-nitrophenol
  作者：Ruphino Zugle、Tebello Nyokong

  DOI：10.1016/j.molcata.2012.02.010

  日期：2012.6

  The photophysical and photochemical behavior of two phthalocyanine complexes of lutetium peripherally substituted with tetraphenoxy and tetra-2-pyridiloxy groups were studied in solution and when dispersed in polystyrene polymer fiber. The phthalocyanines were found not to fluoresce significantly in solution and not at all within the fiber matrix as compared with standard unsubstituted zinc phthalocyanine. They showed very promising photoactivity in solution with high singlet oxygen quantum yields. Their photoactivity within the polymer fiber matrix was also demonstrated with the photoconversion of 4-nitrophenol, a water pollutant. The photodegradation process with both phthalocyanines follows first order kinetics similar to that observed for the zinc phthalocyanine and the photo-products were found to be hydroquinone, benzoquinone and 4-nitrocatechol. (C) 2012 Elsevier B.V. All rights reserved.
• The photophysicochemical properties and photodynamic therapy activity of In and Zn phthalocyanines when incorporated into individual or mixed Pluronic® micelles
  作者：Banele Mike Motloung、Balaji Babu、Earl Prinsloo、Tebello Nyokong

  DOI：10.1016/j.poly.2020.114683

  日期：2020.9

  The synthesis, photophysicochemical properties and photodynamic activity (PDT) of tetra-pyridyloxy (1,2) and benzothiazole (3, 4) substituted indium (III) (1,3) and zinc (2, 4) phthalocyanines (Pcs) and their incorporation into Pluronic (R) F127 and Pluronic L121/F127 mixed micelles (the latter for 3 and 4 only) are presented in this study. The InPcs exhibited higher singlet oxygen (Phi(Delta)) at 0.76 and 0.68 compared to the ZnPc's at 0.47 and 0.44 in dimethyl sulfoxide. The Phi(Delta) values in the presence of Pluronic (R) F127 and in water, were 0.39 and 0.42 for InPcs and 0.23 and 0.37 for ZnPc. The Phi(Delta) values in the presence of Pluronic F127/L121 mixed micelles for complex 3 and 4 were 0.51 and 0.29 in water. The K-p was determined using the water and octanol system. InPcs had larger K-p values suggesting that they are more likely to be taken up by the cancer cells hence they showed better PDT activity. (C) 2020 Elsevier Ltd. All rights reserved.
• Fabrication of efficient nonlinear optical absorber using Zn phthalocyanine-semiconductor quantum dots conjugates
  作者：Sithi Mgidlana、David O. Oluwole、Tebello Nyokong

  DOI：10.1016/j.poly.2018.11.024

  日期：2019.2

  In this paper, we report on the synthesis of Zn(II) phthalocyanine derivatives and their conjugates with core/shell and core/shell/shell semiconductor quantum dots (SQDs). Zn(II) mono amino-carboxyethylphenoxy phthalocyanine (1), Zn(II) mono 3-carboxyphenoxy-tris(pyridin-2-yloxy) phthalocyanine (2) and Zn(II) mono aminophenoxy-tris(benzothiazole) phthalocyanine (3) were synthesized. The photophysical and optical limiting properties of the phthalocyanine (Pc) complexes and their conjugates with SQDs were investigated in dimethyl sulfoxide. The optical limiting behaviour of the Pc complexes and their conjugates were measured by the open aperture Z-scan technique at laser excitation wavelength of 532 nm with 10 ns pulse. The conjugates outperformed the Pc complexes alone with the conjugates of 2-SQDs affording highest nonlinear absorption coefficient (beta(eff)) value of similar to 80 cm/GW and lowest limiting threshold (I-lim) value of similar to 0.27 J.cm(-2) as compared to other samples while complex 1 gave low beta(eff) and high I-lim values of 42.2 cm/GW and 1.39 J.cm(-2), respectively. (C) 2018 Elsevier Ltd. All rights reserved.