2,3,9,10,16,17,23,24-octacarboxyphthalocyanine | 58334-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 2,3,9,10,16,17,23,24-octacarboxyphthalocyanine
• 英文别名: 2,11,20,29,37,38,39,40-Octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13,15,17,19(39),20,22,24,26,28(38),30(37),31,33,35-nonadecaene-6,7,15,16,24,25,33,34-octacarboxylic acid；2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13,15,17,19(39),20,22,24,26,28(38),30(37),31,33,35-nonadecaene-6,7,15,16,24,25,33,34-octacarboxylic acid
• CAS: 58334-40-0
• 化学式: C₄₀H₁₈N₈O₁₆
• 分子量: 866.627
• InChiKey: MTRSPLSEPKFZIS-UHFFFAOYSA-N

物化性质

• 密度：
  1.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  64
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  407
• 氢给体数：
  10
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  2,3,9,10,16,17,23,24-octacarboxyphthalocyanine 在 乙酸酐 作用下， 反应 10.0h， 以97.5%的产率得到2,3,9,10,16,17,23,24-octacarboxy-29,31-dihydrophthalocyanine tetraanhydride
  参考文献：
  名称：

  酞菁四酰亚胺作为溶液可处理电子受体的合成及性能研究

  摘要：

  设计并通过三种途径合成了具有疏水性侧链的可溶性酞菁四酰亚胺（PcTIs）。研究了它们的吸收，荧光，电化学，稳定性，电荷迁移率和几何形状。这些平面共轭化合物具有在550-850 nm处的强烈吸收，-3.92至-3.98 eV的最深最低未占据分子轨道，高于400°C的分解温度和最高4.88×10 -4  cm 2  V -1  s的电子迁移率-1（SCLC）是出色的溶液可处理受体。基于受体CuPcTI-C11的块状异质结太阳能电池的功率转换效率为1.17％，是酞菁衍生物中的最高值。

  DOI：

  10.1016/j.dyepig.2019.107980
• 作为产物：
  描述：

  均苯四甲酸二酐 在 ammonium hydroxide 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 尿素 、 sodium hydroxide 、 三氯氧磷 、 正己醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.94h， 生成 2,3,9,10,16,17,23,24-octacarboxyphthalocyanine
  参考文献：
  名称：

  Synthesis and photophysicochemical studies of non-metal 2,3,9,10,16,17,23,24-octacarboxyphthalocyanine

  摘要：

  报告了一种新的制备方法以及非金属 2,3,9,10,16,17,23,24-octacarboxyphthalocyanine 的特性（溶解性、聚集性、光谱发光特性、单线态氧和光漂白量子产率）。此外，还介绍了电离状态对该染料光物理化学特性的影响。

  DOI：

  10.1142/s1088424612501301

文献信息

• Liquid crystalline octaalkoxycarbonyl phthalocyanines: design, synthesis, electronic structure, self-aggregation and mesomorphism
  作者：Sergey Sergeyev、Eric Pouzet、Olivier Debever、Jeremy Levin、Johannes Gierschner、Jérôme Cornil、Rafael Gómez Aspe、Yves Henri Geerts

  DOI：10.1039/b617856a

  日期：——

  We describe a practical synthesis of octaalkoxycarbonyl phthalocyanines that are well soluble in various organic solvents and form liquid crystalline columnar mesophases at room temperature. The ground-state geometry, HOMO/LUMO energies, vertical transition energies and the corresponding oscillator strengths have been calculated for the isolated molecules. The redox behavior of octaalkoxycarbonyl phthalocyanines was investigated by cyclic voltammetry and their aggregation in solution by 1H NMR spectroscopy. The supramolecular structure of the liquid crystalline mesophase of a novel phthalocyanine bearing branched alkyl chains was studied by powder X-ray diffraction. The length and branching of peripheral alkyl chains are found to be two structural parameters affecting the formation of mesophases and self-aggregation in solution.

  我们描述了一种实用的八烷氧羰基酞菁合成方法，这些化合物在多种有机溶剂中具有良好的溶解性，并在室温下形成液晶柱状介观相。我们对孤立分子的基态几何结构、最高占据分子轨道（HOMO）/最低未占据分子轨道（LUMO）能量、垂直跃迁能量及其相应的振子强度进行了计算。通过循环伏安法研究了八烷氧羰基酞菁的氧化还原行为，并通过1H核磁共振光谱法研究了它们在溶液中的聚集。利用粉末X射线衍射技术研究了一种新型酞菁在液晶介观相中的超分子结构，该酞菁带有支链烷基链。研究发现，外围烷基链的长度和分支是影响介观相形成和溶液中自聚集的两个结构参数。
• Transition temperature engineering of octaalkoxycarbonyl phthalocyanines
  作者：Sergey Sergeyev、Olivier Debever、Eric Pouzet、Yves Henri Geerts

  DOI：10.1039/b704344a

  日期：——

  We have described a simple approach to the transition temperature engineering in metal-free mesogenic octaalkoxycarbonyl phthalocyanines Pc(COOR)8. The method is based on the esterification of a common octaacid precursor with binary mixtures of alcohols. Variation of the length of alkyl chain and the ratio of components in the starting mixtures of alcohols resulted in phthalocyanines comprising multiple components, yet with well-defined and reproducible composition that was reflected in well-defined and reproducible thermotropic properties. Linear dependence between isotropization temperatures and average length of alkyl chains in Pc(COOR)8 was demonstrated.

  我们介绍了一种简单的无金属介源八烷氧基羰基酞菁 Pc(COOR)8 过渡温度工程方法。该方法基于普通八酸前体与二元醇混合物的酯化反应。改变起始醇混合物中烷基链的长度和各组分的比例，可得到由多种组分组成的酞菁，但其组成明确且可重现，这反映在明确且可重现的趋热特性上。Pc(COOR)8 的各向同性温度与烷基链的平均长度呈线性关系。
• Maximizing Electroactive Sites in a Three‐Dimensional Covalent Organic Framework for Significantly Improved Carbon Dioxide Reduction Electrocatalysis
  作者：Bin Han、Yucheng Jin、Baotong Chen、Wei Zhou、Baoqiu Yu、Chuangyu Wei、Hailong Wang、Kang Wang、Yanli Chen、Banglin Chen、Jianzhuang Jiang

  DOI：10.1002/anie.202114244

  日期：2022.1.3

  3D imide-bonded covalent organic framework (COF) composed of cobalt-phthalocyanine subunits has been prepared and used in CO2 reduction reaction electrocatalysis, showing the high CO2-to-CO conversion Faradaic efficiency. In particular, the active electrocatalytic centers and current density (jCO) of this 3D COF have been significantly improved in comparison to that of the 2D COF electrocatalyst with

  已经制备了由钴-酞菁亚基组成的 3D 酰亚胺键合共价有机骨架 (COF)，并将其用于 CO 2还原反应电催化，显示出高 CO 2到 CO 的法拉第效率。特别是，与具有相同酞菁亚单元的 2D COF 电催化剂相比，这种 3D COF的活性电催化中心和电流密度（j CO）得到了显着改善。
• Water-soluble manganese phthalocyanines
  作者：Olga Dolotova、Olga Yuzhakova、Ludmila Solovyova、Ekaterina Shevchenko、Vladimir Negrimovsky、Evgeny Lukyanets、Oleg Kaliya

  DOI：10.1142/s1088424613500818

  日期：2013.8

  Three new substituted manganese phthalocyanines (PcMns), wich are water-soluble, have been synthesized with good yields (70–80%) and high purity. Pyridiniummethyl- and cholinylsubstituted phthalocyanines have been obtained from the chloromethylsubstituted PcMns , while octacarboxysubstituted complex has been synthesized from metal-free octacarboxyphthalocyanine tetraanhydride. Compounds were characterized by elemental analysis and mass, IR and UV-vis spectroscopy. In general, coordination chemistry of the compounds studied is similar to this one of liposoluble PcMns but some new findings have been obtained. Three coordination forms — PcMn ( II ), PcMn ( III ) X ( X = Cl ^-, OAc ^-, …) and [ LPcMn ( III )]₂ O ( L = Py , Et ₃ N , …) have been obtained for all the new compounds. The equilibrium between three electronic isomers — Pc^+• Mn ( I ) × L , PcMn ( II ) × nL , (n = 1, 2) and Pc^-• Mn ( III ) × 2 L has been observed in PcMn aqueous solutions upon the addition of organic bases L ( Py , Et ₃ N , …).

  我们合成了三种新的取代锰酞菁（PcMns），它们均可溶于水，且收率高（70-80%）、纯度高。从甲基氯取代的 PcMns 中得到了甲基吡啶和甲基胆烷基取代的酞菁，而从无金属的八羧基酞菁四酸酐中合成了八羧基络合物。化合物通过元素分析和质量、红外和紫外-可见光谱进行表征。总的来说，所研究化合物的配位化学与脂溶性 PcMns 相似，但也有一些新发现。所有新化合物都有三种配位形式 - PcMn ( II ), PcMn ( III ) X ( X = Cl -, OAc -, ...) 和 [ LPcMn ( III )]2 O ( L = Py , Et 3 N , ...) 。在 PcMn 水溶液中加入有机碱 L（Py、Et 3 N、......）后，观察到三种电子异构体--Pc+- Mn ( I ) × L、PcMn ( II ) × nL（n = 1、2）和 Pc-- Mn ( III ) × 2 L 之间的平衡。
• Dulog, Lothar; Gittinger, Andreas, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1992, vol. 213, p. 31 - 42
  作者：Dulog, Lothar、Gittinger, Andreas

  DOI：——

  日期：——