4,5-bis(1,4,7,10-tetraoxaundecyl)phthalonitrile | 156000-26-9

• 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(1,4,7,10-tetraoxaundecyl)phthalonitrile
• 英文别名: 4,5-Bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene-1,2-dicarbonitrile
• CAS: 156000-26-9
• 化学式: C₂₂H₃₂N₂O₈
• 分子量: 452.505
• InChiKey: UIOMPGXXZDTCKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  576.9±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：
  32
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5-bis(1,4,7,10-tetraoxaundecyl)phthalonitrile 在 氨 、 sodium 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以58%的产率得到5,6-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)isoindoline-1,3-diimine
  参考文献：
  名称：

  以互变异构苯并酞菁为平台的可光活化的可激活近红外光声探针的设计

  摘要：

  由于近红外能够深入组织，因此近红外（NIR）成像技术已在生物学和医学领域引起了广泛关注。但是，很少有稳定，可激活的分子探针可以利用波长范围超过800 nm的NIR光。在此，我们报告了一种基于互变异构苯并酞菁（BPcs）的用于光声成像的新的可激活NIR系统。我们发现，游离羟基的存在对于BPcs的近红外吸收至关重要。合成的水溶性羟基BPcs具有很高的光稳定性，并且没有荧光，这是光声成像的理想功能。我们合成了BPcs，其中的游离羟基被酯酶不稳定或H 2 O 2掩盖不稳定组。当存在酯酶或H 2 O 2时，在880 nm处进行近红外激发时，这些被羟基掩盖的BPcs的光声信号分别增加。这些是利用900 nm左右的NIR光激活的探针的罕见示例。

  DOI：

  10.1002/anie.201903303
• 作为产物：
  描述：

  1,2-二{2-[2-(2-甲氧基乙氧基)乙氧基]乙氧基}苯 在 溴 、 碘 、 铁粉 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4,5-bis(1,4,7,10-tetraoxaundecyl)phthalonitrile
  参考文献：
  名称：

  Poly(oxyethylene)-Substituted Copper and Lutetium Phthalocyanines

  摘要：

  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.

  DOI：

  10.1021/jp960504c
• 作为试剂：
  描述：

  1,2-dicyano-4,5-bis(dodecyloxy)benzene 在 N,N-二甲基乙醇胺 、 氨 、 sodium methylate 、 4,5-bis(1,4,7,10-tetraoxaundecyl)phthalonitrile 作用下， 以0.3%的产率得到2,3,9,10,16,17-hexa(dodecyloxy)-23,24-di(1,4,7,10-tetraoxaundecyl)phthalocyanine
  参考文献：
  名称：

  Clarkson, Guy J.; McKeown, Neil B.; Treacher, Kevin E., Journal of the Chemical Society. Perkin transactions I, 1995, # 14, p. 1817 - 1824

  摘要：

  DOI：

文献信息

• A Janus-Type Phthalocyanine for the Assembly of Photoactive DNA Origami Coatings
  作者：Asma Rahali、Ahmed Shaukat、Verónica Almeida-Marrero、Bassem Jamoussi、Andrés de la Escosura、Tomás Torres、Mauri A. Kostiainen、Eduardo Anaya-Plaza

  DOI：10.1021/acs.bioconjchem.1c00176

  日期：2021.6.16

  their aggregation while providing the ability to adhere on DNA origami nanostructures via reversible electrostatic interactions. On the other hand, triethylene glycol moieties render a water-soluble and chemically inert corona that can stabilize the structures. This approach provides insight into the molecular design and synthesis of Janus-type sensitizers that can be combined with biomolecules, rendering

  新型光敏剂结构的设计和合成是迈向新型多功能分子材料的关键一步。光敏 Janus 型分子通过呈现两个可正交使用的明确定义的化学官能团，为此类系统提供了有趣的构建模块。本文报道了一种多功能酞菁，它带有一个庞大且带正电的部分，可阻碍它们的聚集，同时提供通过可逆静电相互作用粘附在 DNA 折纸纳米结构上的能力。另一方面，三甘醇部分提供水溶性和化学惰性的电晕，可以稳定结构。这种方法提供了对 Janus 型敏化剂的分子设计和合成的深入了解，这些敏化剂可以与生物分子结合，产生光学活性的生物杂种。
• Aggregation, Complexation with Guest Molecules, and Mesomorphism of Amphiphilic Phthalocyanines Having Four- or Eight Tri(ethylene oxide) Chains
  作者：Nagao Kobayashi、Ryuji Higashi、Kazuyuki Ishii、Kazuaki Hatsusaka、Kazuchika Ohta

  DOI：10.1246/bcsj.72.1263

  日期：1999.6

  Zinc and metal-free amphiphilic phthalocyanines (pcs) substituted by four or eight tri(ethylene oxide) chains (3,6,9-trioxadecyloxy groups) (H2(4EGpc), [Zn(4EGpc)], H2(8EGpc), and [Zn(8EGpc)] in Fig. 1)} have been prepared in order to study their aggregation in water, dioxane, and dioxane/water mixtures, their complexation phenomena with guest molecules in benzene, and mesomorphism in the neat state. In particular, tetra-substituted pcs have C4h symmetry and do not contain other positional isomers. [Zn(8EGpc)] forms aggregates in water and water–organic solvent mixtures; the extent of this was examined by electronic absorption and fluorescence spectroscopy. 1H NMR and fluorescence spectroscopy indicated that H2- and [Zn(8EGpc)] form inclusion complexes with quinones in benzene via hydrogen bonding. Benzoquinones with more hydroxy groups form complexes more effectively, plausibly laterally outside of the pc plane. From the higher field shift of the 1H singals of 2,2′-dihydroxy-1,1′-binaphthyl (BINAP) in the presence of [Zn(8EGpc)], BINAP molecules were suggested to lie above or below the pc plane. The mesomorphism of H2(8EGpc), [Zn(4EGpc)], and H2(4EGpc) was studied. In the case of H2(8EGpc), the discotic hexagonal ordered columnar (Dho) phase was seen in the range of from room temperature to 265 °C. However, liquid-crystalline phases were not observed for H2(4EGpc) and [Zn(4EGpc)].

  为了研究锌和无金属两亲性酞菁在水和二恶烷/水混合物中的聚集、在苯中与客体分子的络合现象以及在纯净状态下的中形性，我们制备了被四或八个三环氧乙烷链（3,6,9-三氧杂十一烷氧基基团）取代的锌和无金属两亲性酞菁（pcs）（图 1 中的 H2(4EGpc)、[Zn(4EGpc)]、H2(8EGpc)和 [Zn(8EGpc)]）}。1）}，以研究它们在水、二噁烷和二噁烷/水混合物中的聚集、在苯中与客体分子的络合现象以及在纯净状态下的中形性。其中，四取代 pcs 具有 C4h 对称性，不包含其他位置异构体。[Zn(8EGpc)] 在水和水-有机溶剂混合物中形成聚集体；电子吸收和荧光光谱分析了这种聚集体的程度。1H NMR 和荧光光谱表明，H2- 和[Zn(8EGpc)]通过氢键与苯中的醌类化合物形成包合物。羟基较多的苯醌能更有效地形成络合物，可能是在 pc 平面外的侧面。根据 2,2′-二羟基-1,1′-联萘（BINAP）的 1H 单值在[Zn(8EGpc)]存在下的较高场移，可以认为 BINAP 分子位于 pc 平面的上方或下方。研究了 H2(8EGpc)、[Zn(4EGpc)] 和 H2(4EGpc) 的介形。对于 H2(8EGpc)，在室温至 265 °C 的范围内出现了盘状六方有序柱状（Dho）相。然而，在 H2(4EGpc) 和 [Zn(4EGpc)] 中没有观察到液晶相。
• Novel series of peripherally phthalocyanines (Zn, Pd and Cu): Spectroscopic studies
  作者：Asma Rahali、Verónica Almeida-Marrero、Andrés de la Escosura、Tomás Torres、Raoudha Abderrahim

  DOI：10.2174/1570178620666221227162819

  日期：2022.12.27

  A new series of metallophthalocyanines (MPc) containing metals such as : Zn (II), Cu (II) and, Pd (II) were designed, synthesized, and characterized, using MS, IR and UV-Vis spectroscopy. A Suzuki cross-coupling reaction was investigated by using the Pd(dppf)Cl2 as a catalyst and cesium carbonate as a base to improve the yield of the precursor 2.6-di(pyridin-3-yl)- phenyl benzyl ether. The changes

  使用 MS、IR 和 UV-Vis 光谱设计、合成和表征了一系列新的金属酞菁 (MPc)，其中包含 Zn (II)、Cu (II) 和 Pd (II) 等金属。以 Pd(dppf)Cl2 为催化剂，碳酸铯为碱，研究了铃木交叉偶联反应，以提高前体 2.6-二(吡啶-3-基)-苯基苄基醚的产率。金属、取代基和位置的变化增加了 Q 带值，从单取代到八取代大环，从 Pd 到 Cu 到 Zn 络合物。所有 MPc 都显示出非常相似的红外光谱。
• Paramagnetic metal-phthalocyanine complex compounds and contrast agent using the same
  申请人：——

  公开号：US20040214810A1

  公开（公告）日：2004-10-28

  The present invention provides a novel paramagnetic metal-phthalocyanine complexes and pharmaceutically acceptable salts thereof, which are useful as contrast agents for MRI (Magnetic Resonance Imaging), diagnostic X-ray imaging and computed tomography (CT). The present invention also provides contrast agents for imaging, comprising the new paramagnetic metal-phthalocyanine complexes. The new contrast agents of the present invention show high imaging enhancement effects at lower concentration and are safer than the previously reported contrast agents.

  本发明提供了一种新型顺磁金属-酞菁配合物及其药学上可接受的盐类，可用作核磁共振成像（MRI）、X 射线成像诊断和计算机断层扫描（CT）的造影剂。 本发明还提供了由新型顺磁性金属-酞菁配合物组成的成像造影剂。本发明的新型造影剂在较低的浓度下就能显示出较高的成像增强效果，而且比以前报道的造影剂更安全。
• Ionoelectronics. Cation-Induced Nonlinear Complexation: Crown Ether- and Poly(ethylene oxide)-Substituted Lutetium Bisphthalocyanines
  作者：Thierry Toupance、Vefa Ahsen、Jacques Simon

  DOI：10.1021/ja00091a046

  日期：1994.6

  Lutetium bisphthalocyanines symmetrically substituted with crown ether macrocycles ([(15-C-5)(4)Pc]Lu-2, [(18-C-6)(4)Pc]Lu-2) or linear poly(ethylene oxide) chains ([(RO)(8)Pc]Lu-2) have been synthesized and characterized. An unsymmetrical complex ([(15-C-5)(4)Pc]Lu[Pc(OR)(8)]) is also described. The selectivity of complexation toward alkali cations is determined by the picrate extraction method. Titration curves have been obtained by UV-visible spectroscopy, showing that large alkali cations induce the formation of aggregates via a positive cooperativity effect. A sigmoidal titration curve is obtained for the couple [(18-C-6)(4)Pc]Lu-2/Rb+. The shape of the curve is very similar to the one obtained for the complexation of O-2 by hemoglobin, where a nonlinear binding process is well established. The obtainment of this phenomenon is a key step toward the realization of ionoelectronics networks.