4,5-Bis(1,4,7-trioxaoctyl)phthalonitrile | 178813-97-3

• 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(1,4,7-trioxaoctyl)phthalonitrile
• 英文别名: 4,5-di[poly(oxyethylene)]phthalonitrile；4,5-Bis[2-(2-methoxyethoxy)ethoxy]benzene-1,2-dicarbonitrile
• CAS: 178813-97-3
• 化学式: C₁₈H₂₄N₂O₆
• 分子量: 364.398
• InChiKey: MHPZTRXETUCKCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  515.2±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,5-Bis(1,4,7-trioxaoctyl)phthalonitrile 在 C₅H₁₁OLi 、 4-(3',5'-Dibenzyloxy)benzyloxyphthalonitrile 作用下， 以 戊醇 为溶剂， 生成 2-(3',5'-Dibenzyloxy)benzyloxy-9,10,16,17,23,24-hexa(1,4,7-trioxaoctyl)phthalocyanine 、 2,3,9,10,16,17,23,24-octakis(3,6-dioxaheptyloxy)phthalocyanine
  参考文献：
  名称：

  Phthalocyanines substituted with dendritic wedges: glass-forming columnar mesogens

  摘要：

  通过用聚芳醚树状楔形物对酞菁大环进行外围取代，制备出既受酞菁核心的柱状自组装特性主导，又受树状取代基玻璃形成特性的材料。

  DOI：

  10.1039/a801799i
• 作为产物：
  描述：

  1-溴-2-(2-甲氧基乙氧基)乙烷 在 氢氧化钾 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4,5-Bis(1,4,7-trioxaoctyl)phthalonitrile
  参考文献：
  名称：

  The synthesis and photophysical properties of polyether substituted phthalocyanines of potential use in photodynamic therapy

  摘要：

  报告并讨论了一系列聚醚取代的金属和游离基酞菁的合成、光物理性质和单态氧产率，背景是这些化合物作为血红素卟啉衍生物（HpD）在癌症光动疗法（PDT）中潜在应用的可能性。采用纳秒激光闪光光解和脉冲辐射解法研究了酞菁的单重态。单重态光吸收最大值位于约510到525纳米，单重态形成的量子产率（ϕT）范围为0.14到0.32。单重态寿命在26到155微秒之间。酞菁的单重态（T1）向基态分子氧O23Σg-转移能量以产生单态氧O21ωg的效率很高，且在完全氘化苯中提供了建立平衡的证据，方程式（a）。通过时间分辨近红外发光测定的单态氧量子产率（ϕΔ）与单重态产率相当，这表明高比例的猝灭相遇导致单态氧的形成。金属酞菁的光物理性质依赖于中心金属离子的相对原子质量和磁性质。

  DOI：

  10.1039/a701079f

文献信息

• The Synthesis and Glass-Forming Properties of Phthalocyanine-Containing Poly(aryl ether) Dendrimers
  作者：Matthew Brewis、Guy J. Clarkson、Madeleine Helliwell、Andrea M. Holder、Neil B. McKeown

  DOI：10.1002/1521-3765(20001215)6:24<4630::aid-chem4630>3.0.co;2-f

  日期：2000.12.15

  phthalocyanine-containing dendrimers are described. Peripheral substitution of phthalocyanine (Pc) with four poly(aryl ether) dendritic wedges (1st, 2nd or 3rd generation) produces materials whose properties are dominated both by the columnar self-association of the Pc core and by the glass-forming character of the dendritic substituents. Asymmetric Pcs containing a single poly(aryl ether) dendron display

  描述了许多含酞菁的树枝状大分子的合成，结构表征和性质。用四个聚（芳醚）树枝状楔形物（第一代，第二代或第三代）对酞菁（Pc）进行外围替代，所制得的材料其性能主要由Pc芯的柱状自缔合和玻璃的玻璃形成特性决定树状取代基。包含单个聚（芳基醚）树突的不对称Pcs显示柱状中间相，其结构可在室温下冷冻成各向异性玻璃。将树枝状楔形物放置在酞菁硅的轴向位置会阻止自缔合，并提供可用于制造具有高玻璃化转变温度的坚固，各向同性的Pc固溶体的材料。
• Synthesis, Characterization, and OFET Properties of Amphiphilic Heteroleptic Tris(phthalocyaninato) Europium(III) Complexes with Hydrophilic Poly(oxyethylene) Substituents
  作者：Renjie Li、Pan Ma、Shuai Dong、Xianyao Zhang、Yanli Chen、Xiyou Li、Jianzhuang Jiang

  DOI：10.1021/ic7016825

  日期：2007.12.1

  A series of amphiphilic heteroleptic tris(phthalocyaninato) europium complexes with hydrophilic poly(oxyethylene) heads and hydrophobic alkoxy tails Pc[(OC2H4)2OCH3]8}EuPc[(OC2H4)2OCH3]8}Eu[Pc(OCnH2n + 1)8] (n = 6, 8, 10,12) (1-4) were designed and prepared from the reaction between homoleptic bis(phthalocyaninato) europium compound Pc[(OC2H4)2OCH3]8}EuPc[(OC2H4)2OCH3]8} and metal-free 2,3,9,10

  一系列具有亲水性聚（氧乙烯）头和疏水性烷氧基尾巴的两亲性三（邻苯二甲氧基）to络合物Pc [（OC2H4）2OCH3] 8} Eu Pc [（（OC2H4）2OCH3] 8} Eu [Pc（OCnH2n + 1 ）8]（n = 6，8，10,12）（1-4）由均一的双（酞菁基））化合物Pc [（（OC2H4）2OCH3] 8} Eu Pc [（OC2H4 ）2OCH3] 8}和不含金属的2,3,9,10,16,17,23,24-辛基（烷氧基）酞菁H2Pc（OCnH2n +1）8（n = 6，8，10,12）中在沸腾的1,2,4-三氯苯（TCB）中存在Eu（acac）3.H2O（Hacac =乙酰丙酮）。这些新颖的夹心三层复合体已通过多种光谱方法进行了表征，并已进行了电化学研究。借助Langmuir-Blodgett（LB）技术，这些典型的两亲性三层复合体已被制成具有非常规底部接触结
• Poly(oxyethylene)-Substituted Copper and Lutetium Phthalocyanines
  作者：Thierry Toupance、Pierre Bassoul、Ludovic Mineau、Jacques Simon

  DOI：10.1021/jp960504c

  日期：1996.1.1

  A new family of nonionic water-soluble lutetium bisphthalocyanines and a copper monophthalocyanine have been synthesized and characterized. Optical absorption determinations demonstrate aggregation processes in water. Optical microscopy, differential scanning calorimetry (DSC), and X-ray diffraction measurements have also been performed on the materials. The substituted copper complex yields a hexagonal columnar Liquid crystal above 62 degrees C; this mesophase can incorporate up to 16% (w/w) of triethylene glycol without significant disturbance of the structure, One of the substituted lutetium bisphthalocyanines affords a tetragonal columnar mesophase; the other bisphthalocyanine derivatives show only highly ordered crystalline like phases. Conductivity measurements have been carried out on thin films of the previous derivatives to determine the relative electronic and ionic conduction contributions.
• The synthesis and photophysical properties of polyether substituted phthalocyanines of potential use in photodynamic therapy
  作者：Sarah Foley、Gurnos Jones、Raffaelle Liuzzi、David J. McGarvey、Martin H. Perry、T. George Truscott

  DOI：10.1039/a701079f

  日期：——

  The synthesis, photophysical properties and singlet oxygen yields of a range of polyether substituted metallo and free-base phthalocyanines are reported and discussed in the context of the potential use of these compounds as alternatives to haematoporphyrin derivatives (HpD) in the photodynamic therapy (PDT) of cancer. The triplet states of the phthalocyanines have been studied in benzene and methanol using nanosecond laser flash photolysis and pulse radiolysis. Triplet state absorption maxima occur at ca. 510 to 525 nm and the quantum yields of triplet formation (ϕT) lie in the range 0.14 to 0.32. Triplet state lifetimes are in the range 26 to 155 µs. Energy transfer from the triplet state (T1) of the phthalocyanines to ground state molecular oxygen O23Σg- to produce singlet oxygen O21ωg is efficient and evidence is presented for the establishment of an equilibrium in perdeuterated benzene, eqn. (a).Singlet oxygen quantum yields (ϕΔ), determined by time resolved near infrared luminescence, are comparable with the triplet yield suggesting a high proportion of quenching encounters result in the formation of singlet oxygen.The photophysical properties of the metallophthalocyanines are dependent on the relative atomic mass and the magnetic properties of the central metal ion.

  报告并讨论了一系列聚醚取代的金属和游离基酞菁的合成、光物理性质和单态氧产率，背景是这些化合物作为血红素卟啉衍生物（HpD）在癌症光动疗法（PDT）中潜在应用的可能性。采用纳秒激光闪光光解和脉冲辐射解法研究了酞菁的单重态。单重态光吸收最大值位于约510到525纳米，单重态形成的量子产率（ϕT）范围为0.14到0.32。单重态寿命在26到155微秒之间。酞菁的单重态（T1）向基态分子氧O23Σg-转移能量以产生单态氧O21ωg的效率很高，且在完全氘化苯中提供了建立平衡的证据，方程式（a）。通过时间分辨近红外发光测定的单态氧量子产率（ϕΔ）与单重态产率相当，这表明高比例的猝灭相遇导致单态氧的形成。金属酞菁的光物理性质依赖于中心金属离子的相对原子质量和磁性质。
• Phthalocyanines substituted with dendritic wedges: glass-forming columnar mesogens
  作者：Matthew Brewis、Guy J. Clarkson

  DOI：10.1039/a801799i

  日期：——

  Peripheral substitution of the phthalocyanine macrocycle with poly(aryl ether) dendritic wedges produces materials whose properties are dominated both by the columnar self-association of the phthalocyanine core and by the glass-forming character of the dendritic substituents.

  通过用聚芳醚树状楔形物对酞菁大环进行外围取代，制备出既受酞菁核心的柱状自组装特性主导，又受树状取代基玻璃形成特性的材料。