4-chloro-5-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile | 1395920-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-chloro-5-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile
• 英文别名: 4-Chloro-5-[2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy]benzene-1,2-dicarbonitrile
• CAS: 1395920-44-1
• 化学式: C₁₃H₄ClF₉N₂O₃
• 分子量: 442.625
• InChiKey: LWXMVKPEBJKAAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-chloro-5-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile 在 N,N-二甲基乙醇胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 7.0h， 以6%的产率得到
  参考文献：
  名称：

  Synthesis and characterization of novel fluoroether-substituted phthalocyanines

  摘要：

  The synthesis of 1H,1H-nonafluoro-3,6-dioxaheptan-1-ol with 4-nitrophthalonitrile and 4,5-dichlorophthalonitrile in the presence of K2CO3 leads to the formation of 4-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile (1), 4-chloro-5-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy] ethoxy)-phthalonitrile (2), and 4,5-bis{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile (3), respectively. Metal free phthalocyanines were synthesized by tetramerization of the phthalonitriles in 2-(dimethylamino)ethanol while metallophthalocyanines were prepared in the presence of zinc, cobalt or nickel salts. The new compounds were characterized by elemental analysis. IR, H-1, and F-19 NMR and UV-Vis spectroscopy as well as mass spectrometry. The fluoroether substituted Pcs are best soluble in polar solvents such as acetone and THF. Crown Copyright (C) 2012 Published by Elsevier B.V. rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.023
• 作为产物：
  描述：

  1H,1H-九氟-3,6-二噁-1-庚醇 、 4,5-二氯邻苯二甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以52%的产率得到4-chloro-5-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile
  参考文献：
  名称：

  Synthesis and characterization of novel fluoroether-substituted phthalocyanines

  摘要：

  The synthesis of 1H,1H-nonafluoro-3,6-dioxaheptan-1-ol with 4-nitrophthalonitrile and 4,5-dichlorophthalonitrile in the presence of K2CO3 leads to the formation of 4-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile (1), 4-chloro-5-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy] ethoxy)-phthalonitrile (2), and 4,5-bis{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile (3), respectively. Metal free phthalocyanines were synthesized by tetramerization of the phthalonitriles in 2-(dimethylamino)ethanol while metallophthalocyanines were prepared in the presence of zinc, cobalt or nickel salts. The new compounds were characterized by elemental analysis. IR, H-1, and F-19 NMR and UV-Vis spectroscopy as well as mass spectrometry. The fluoroether substituted Pcs are best soluble in polar solvents such as acetone and THF. Crown Copyright (C) 2012 Published by Elsevier B.V. rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.023

文献信息

• Photophysical and photochemical properties of fluoroether-substituted zinc(II) and titanium(IV) phthalocyanines
  作者：İlke Gürol、Gülay Gümüş、Deniz Kutlu Tarakci、Ömer Güngör、Mahmut Durmuş、Vefa Ahsen

  DOI：10.1142/s1088424618500074

  日期：2018.1

  The synthesis and characterization of novel zinc(II) (1a–4a) and oxo-titanium(IV) (1b–4b) phthalocyanine derivatives bearing 1H,1H-nona?uoro-3,6-dioxaheptan-1-ol groups are described for the first time. These phthalocyanines (1a–4a and 1b–4b) were characterized by elemental analysis and different spectroscopic techniques such as UV-vis, [Formula: see text]H NMR, FTIR and mass. Furthermore, the photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation) properties of these phthalocyanines were investigated in tetrahydrofuran (THF) solution. The influence of the number of the substituted groups (tetra or octa), position of the substituents (peripheral or non-peripheral) and central metal atom (zinc or titanium) on the photophysical and photochemical properties of these phthalocyanines were evaluated.

  本文首次描述了带有 1H,1H-nona?uoro-3,6-dioxaheptan-1-ol 基团的新型锌（II）（1a-4a）和氧代钛（IV）（1b-4b）酞菁衍生物的合成和表征。这些酞菁（1a-4a 和 1b-4b）通过元素分析和不同的光谱技术（如紫外-可见光、[式：见正文]H NMR、傅立叶变换红外光谱和质量）进行了表征。此外，还研究了这些酞菁在四氢呋喃（THF）溶液中的光物理（荧光量子产率和寿命）和光化学（单线态氧生成和光降解）特性。评估了取代基的数目（四或八）、取代基的位置（外围或非外围）以及中心金属原子（锌或钛）对这些酞菁的光物理和光化学特性的影响。