4,5-bis(2,2,2-trifluoroethoxy)phthalonitrile | 215796-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-bis(2,2,2-trifluoroethoxy)phthalonitrile
• 英文别名: 4,5-bis(2,2,2-trifluoroethoxy)benzene-1,2-dicarbonitrile
• CAS: 215796-20-6
• 化学式: C₁₂H₆F₆N₂O₂
• 分子量: 324.182
• InChiKey: CXCDYPRESGHUAF-UHFFFAOYSA-N

物化性质

• 沸点：
  357.2±42.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5-bis(2,2,2-trifluoroethoxy)phthalonitrile 在 zinc(II) chloride 作用下， 以 N,N-二甲基乙醇胺 为溶剂， 反应 24.0h， 以67%的产率得到zinc 2,3,9,10,16,17,23,24-octakis(2,2,2-trifluoroethoxy)phthalocyaninate
  参考文献：
  名称：

  Sukeguchi, Daisuke; Yoshiyama, Hideyuki; Shibata, Norio, Heterocyclic Communications, 2009, vol. 15, # 3, p. 195 - 202

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-二溴苯-1,2-二醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 4,5-bis(2,2,2-trifluoroethoxy)phthalonitrile
  参考文献：
  名称：

  Study of Substituent Effects on the Photoconductivity of Soluble 2,(3)- and 1,(4)-Substituted Phthalocyaninato- and Naphthalocyaninatotitanium(IV) Oxides

  摘要：

  Soluble alkyl (II, 8a,b), fluoroalkyl,(4a), and fluoroalkoxy (4b,c, 8c) 1,(4)- or 2,(3)-substituted phthalocyaninato- and linear 2,(3)- and-angular 1,(2)-annulated naphthalocyaninatotitanium(IV) oxides 10, 12, and 14 were synthesized and characterized with regard to their spectroscopic, photophysical, and photochemical properties. While alkyl- and fluoroalkoxy-substituted compounds are highly soluble in nonpolar solvents, e.g., hexane, fluoroalkyl-substituted compounds are better soluble in polar aprotic solvents such as acetone. The stability against photooxidation in solution is' enhanced on going-from alkylated phthalocyanines 1,(4)-(C(5)H(11))(8)PcTiO (8a), 1,(4)-(C(6)H(13))(8)PcTiO (4b), and 2,(3)-(C(4)H(9))(8)PcTiO (II) to fluorinated phthalocyanines 2,(3)-(CF(3))(4)PcTiO (4a), 2,(3)-(CF(3)CH(2)O)(4)PcTiO (4b), and 2,(3)-(CF(3)CH(2)O)(8)PcTiO (4c), from phthalocyanines to naphthalocyanines (tert-butyl)(4)-2,(3)-NcTiO (10), 1,(2)-NcTiO (12), and (tert-butyl)(4)-1,(2)-NdTiO (14), and on going from 2,(3)-substituted 4a-c to 1,(4)-substituted phthalocyanines 8a-c. Thin films of these compounds, prepared by either vacuum deposition or spin casting, are classified into three types according to increasing intermolecular pi-pi interactions. Type alpha films, characterized:by absence of exciton splitting, are formed from 1,(4)-substituted phthalocyanines 8a-c. These films show low dark conductivities and photoconductivities and are considerably sensitive to photooxidation. Type beta films, characterized by weak exciton splitting, are formed from fluorinated phthalocyanines 4a-c as well as from rapidly deposited 2,(3)-substituted phthalocyanines II and the unsubstituted PcTiO (I). These films show enhanced photoconductivity and are generally more stable against photooxidation than type alpha films. Type gamma films, formed by slow deposition of II, 10 and unsubstituted phthalocyanine I, are classified by a largely red-shifted B-band absorbing in the near-IR. These films are highly photosensitive as well as stabilized against photooxidation. Steady-state photoconductivities and dark conductivities in thin films are strongly dependent on oxygen partial pressure. Alkylated PcTiO's such as 8a, 8b, and II are found to be p-type conductors (positive oxygen influence on conductivities) like unsubstituted PcTiO (I), whereas angularly annulated naphthalocyanines such as 12 and 14 as well as fluorinated PcTiO's 4a-c are n-type conductors (negative oxygen influence on conductivity). These findings are rationalized by comparison with experimental and theoretical literature data.

  DOI：

  10.1021/ja981644y

文献信息

• Synthesis and optical properties of trifluoroethoxy-substituted double-decker phthalocyanines
  作者：Satoru Mori、Naoya Ogawa、Etsuko Tokunaga、Norio Shibata

  DOI：10.1142/s1088424614500862

  日期：2014.10

  The synthesis of trifluoroethoxy-substituted double-decker phthalocyanines was investigated for the first time. Trifluoroethoxy-substituted phthalonitriles reacted with lanthanide acetylacetonate hydrate in n-octanol in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene when refluxed. La and Eu were chosen as central metals. Phthalonitriles, including one trifluoroethoxy substituent at the α- or β-position, were nicely induced to double-decker phthalocyanines. Phthalonitrile having two trifluoroethoxy substituents at α-positions did not react, although we succeeded in leading β-di-substituted phthalonitrile to double-decker phthalocyanines. Fully trifluoroethoxy-coated phthalonitrile did not react at all. Fluorophobic repulsion and steric hindrance caused by outlying trifluoroethoxy groups could be responsible for the difficulty in the formation of a double-decker structure. Absorption and fluorescence spectra of trifluoroethoxy-substituted double-decker phthalocyanines obtained were also investigated.

  首次研究了三氟乙氧基取代的双层酞菁的合成。在正辛醇中，1,8-二氮杂双环[5.4.0]十一-7-烯存在的情况下，三氟乙氧基取代的酞菁与乙酰丙酮酸镧水合物发生回流反应。La 和 Eu 被选为中心金属。在 α 或 β 位上含有一个三氟乙氧基取代基的酞腈被很好地诱导成双层酞菁。在 α 位有两个三氟乙氧基取代基的邻苯二腈没有发生反应，尽管我们成功地将β-二取代酞腈诱导成了双层酞菁。完全三氟乙氧基包覆的邻苯二腈则完全没有反应。疏氟斥力和外露的三氟乙氧基基团造成的立体阻碍可能是难以形成双层结构的原因。此外，还研究了三氟乙氧基取代的双层酞菁的吸收光谱和荧光光谱。
• A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines: Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines
  作者：Taniyuki Furuyama、Takehito Sato、Nagao Kobayashi

  DOI：10.1021/jacs.5b09853

  日期：2015.11.4

  The first example of an antiaromatic expanded phthalocyanine, classified as a norcorrole of a superphthalocyanine has been prepared and fully characterized. The newly developed phthalonitrile dimerization reaction was a crucial step, which allowed for the bottom-up synthesis of expanded phthalocyanines. Their structure was confirmed by single crystal X-ray diffraction analysis. The 20 π antiaromaticity

  已制备并充分表征了抗芳族膨胀酞菁的第一个实例，归类为超酞菁的去甲酚。新开发的邻苯二甲腈二聚反应是一个关键步骤，它允许自下而上地合成扩大的酞菁。通过单晶X射线衍射分析证实了它们的结构。光学和理论计算表明大环的 20 π 反芳香性。