zinc octacarboxyphthalocyanine

• 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: zinc octacarboxyphthalocyanine
• 英文别名: ZINC;2,11,20,29,37,39-hexaza-38,40-diazanidanonacyclo[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),20,22,24,26,28,30(37),31,33,35-nonadecaene-6,7,15,16,24,25,33,34-octacarboxylic acid
• 化学式: C₄₀H₁₆N₈O₁₆Zn
• 分子量: 930.001
• InChiKey: XQHLZPDPEDTZKZ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  65
• 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：
  375
• 氢给体数：
  8
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  zinc octacarboxyphthalocyanine 在 乙酸酐 作用下， 反应 10.0h， 以97.5%的产率得到(phthalocyanine-2,3:9,10:16,17:23,24-tetrakis(dicarboxanhydride))zinc(II)
  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：

  zinc octa-4,5-carboxyphthalocyanine tetraimide 在 氢氧化钾 作用下， 以 further solvent(s) 为溶剂， 以61%的产率得到zinc octacarboxyphthalocyanine
  参考文献：
  名称：

  摘要：

  The dependence of the quantum yield of photogeneration of singlet oxygen with aluminum sulfophthalocyanines on the degree of their sulfonation was studied. Experiments showed that Fotosens preparation containing, on the average, about three sulfo groups in the macroring in aqueous buffer solution (pH 7.4) exists in the monomeric form and sensitizes singlet oxygen with a quantum yield phi(Delta) 0.42 +/- 0.06. Aluminum tetra-4-sulfophthalocyanine forms dimers, and correspondingly phi(Delta) is lower: 0.22 +/- 0.03. Sulfonated aluminum phthalocyanine containing, on the average, about two sulfo groups in the macroring is aggregated to a significant extent. Addition of Triton X-100 detergent results in partial deaggregation of the dye, and phi(Delta) increases from similar to0.01 to 0.15 +/- 0.02. In the series including previously unknown aluminum phthalocyanines containing residues of phosphonic acids or their esters, and also aluminum and zinc octacarboxyphthalocyanines, the influence of the dye structure on the quantum yield of generation of singlet oxygen suggests participation of axial hydroxy groups in associate formation. These associates are not manifested spectroscopically and generate singlet oxygen inefficiently. The quantum yields phi(Delta) for the monomers and associates are 0.3 and 0.1, respectively.

  DOI：

  10.1023/a:1015402524813

文献信息

• Syntheses of near infrared absorbed phthalocyanines to utilize photosensitizers
  作者：Keiichi Sakamoto、Satoru Yoshino、Makoto Takemoto、Naoki Furuya

  DOI：10.1142/s1088424613500326

  日期：2013.8

  Phthalocyanines have become of major interest as functional colorants for various applications. In order to use various applications especially photosensitizers, the absorption maxima called Q-band of phthalocyanines are required to be shifted to the near infrared region. Substituted phthalocyanine analog alkylbenzopiridoporphyrazins, especially zinc bis(1,4-didecylbenzo)-bis(3,4-pyrido)porphyrazine, and toroidal-shaped phthalocyanines having aminoamine dendric side chains such as toroidal zinc poly(aminoamine)phthalocyanine dendrons were synthesized. Phthalocyanines of two types reportedly use photosensitizers for photodynamic therapy of cancer. The respective efficacies of photodynamic therapy of cancer for zinc bis(1,4-didecylbenzo)-bis(3,4-pyrido)porphyrazine and its regioisomers were estimated using laser-flash photolysis. The capability of using photodynamic therapy for toroidal zinc poly(aminoamine)phthalocyanine dendrons was assessed using a cancer cell culture. Both phthalocyanines were suitable for the use as a photosensitizer as photodynamic therapy of cancer. Then, non-peripheral thioaryl substituted phthalocyanines, 1,4,8,11,15,18,22,25-octakis(thioaryl)phthalocyanines, such as 1,4,8,11,15,18,22,25-octakis(thiophenylmethyl)phthalocyanines, 1,4,8,11,15,18,22,25-octakis(thiophenylmethoxy)phthalocyanines, and 1,4,8,11,15,18,22,25-octakis(thiophenyl tert-butyl)phthalocyanines were also synthesized in order to develop next- generation photovoltaic cells and/or dye-sensitized solar cells. Non-peripheral substituted 1,4,8,11,15,18,22,25-octakis(thioaryl)phthalocyanines exhibited a Q-band in the near infrared region. Electrochemical measurements were performed on the above-mentioned 1,4,8,11,15,18,22,25-octakis(thioaryl)phthalocyanines described above to examine their electron transfer abilities and electrochemical mechanisms. The compounds 1,4,8,11,15,18,22,25-octakis(thioaryl)phthalocyanines are anticipated to be appropriate materials for use in the next generation of photovoltaic cells.

  酞菁作为功能着色剂，在各种应用领域都引起了极大的兴趣。为了实现各种应用，尤其是光敏剂的应用，需要将酞菁的最大吸收波段（Q 波段）转移到近红外区域。我们合成了取代的酞菁类似物烷基苯并吡啶卟嗪，特别是双(1,4-二癸基苯并)-双(3,4-吡啶)卟嗪锌，以及具有氨基树枝状侧链的环状酞菁，如环状多(氨基胺)酞菁树枝状锌。据报道，这两种类型的酞菁可作为光敏剂用于癌症的光动力疗法。利用激光闪烁光解法估算了双(1,4-二癸基苯并)-双(3,4-吡啶并)卟吩锌及其区域异构体各自的癌症光动力疗法疗效。利用癌细胞培养物评估了环状锌聚(氨基胺)酞菁树枝体使用光动力疗法的能力。这两种酞菁都适合用作光敏剂，对癌症进行光动力治疗。还合成了 1,4,8,11,15,18,22,25-八(噻吩甲氧基)酞菁和 1,4,8,11,15,18,22,25-八(噻吩叔丁基)酞菁，以开发新一代光伏电池和/或染料敏化太阳能电池。非周边取代的 1,4,8,11,15,18,22,25-八(硫代芳基)酞菁在近红外区域显示出 Q 波段。对上述 1,4,8,11,15,18,22,25-辛二基（硫芳基）酞菁进行了电化学测量，以研究它们的电子转移能力和电化学机制。预计 1,4,8,11,15,18,22,25-辛二基（硫芳基）酞菁化合物将成为下一代光伏电池的合适材料。
• Carboxy-substituted Phthalocyanine Metal Complexes
  作者：G. P. Shaposhnikov、V. E. Maizlish、V. P. Kulinich

  DOI：10.1007/s11176-005-0450-4

  日期：2005.9

  Metal complexes of carboxy-substituted phthalocyanines differing in the number of carboxy groups and their positions and those having carboxy groups together with other substituents were synthesized, and their spectral and some other properties were studied.

  合成了不同数量和位置的羧基取代酞菁金属配合物，以及同时具有羧基和其他取代基的化合物，并对它们的光谱及其他一些性质进行了研究。
• Synthesis and property study of phthalocyanine tetraimides as solution processable electron acceptors
  作者：Xiaohong Zhao、Xiaoshuai Huang、Ming Hu、Wenqiang Chai、Zhongyi Yuan、Xia Liu、Yu Hu、Chunsheng Cai、Yiwang Chen

  DOI：10.1016/j.dyepig.2019.107980

  日期：2020.2

  Soluble phthalocyanine tetraimides (PcTIs) with hydrophobic side chains were designed and synthesized via three routes. Their absorption, fluorescence, electrochemistry, stability, charge mobility, and geometries were investigated. These planar conjugation compounds with intense absorption in 550–850 nm, deep lowest unoccupied molecular orbitals of −3.92 to −3.98 eV, decomposition temperature higher

  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。
• Phthalocyanines and Related Compounds: XXXVII. Synthesis of Covalent Conjugates of Carboxy-substituted Phthalocyanines with α-Amino Acids
  作者：S. A. Mikhalenko、L. I. Solov'eva、E. A. Luk'yanets

  DOI：10.1023/b:rugc.0000030404.00492.d1

  日期：2004.3

  Methods of synthesis of covalent conjugates of metal complexes of octa-4,5-carboxy- and tetra-4-carboxyphthalocyanine, as well as of octa-6,7-carboxy-2,3-naphthalocyanine with alpha-amino acids, glycine and sarcosine, were developed and certain properties of the products were studied. The prepared conjugates are soluble in organic solvents and water.
• A New Way of Synthesizing Photoactive Metal–Organic Framework Compounds with Macrocyclic Tetrapyrrole Ligands and Their Activity in the Photo-Oxidation of Anthracene under Visible Light
  作者：E. S. Golovashova、V. A. Kulev、E. V. Kudrik、K. E. Moiseeva、T. A. Ageeva、O. I. Koifman

  DOI：10.1134/s0036024420030115

  日期：2020.3

  A fundamentally new approach is proposed for obtaining photoactive metal-organic framework compounds (MOFs). They contain fragments of tetrapyrrol macroheterocycles and exhibit photocatalytic activity in reactions of oxidation of organic compounds. The proposed approach is the preparation of solid solutions of a tetrapyrrole sensitizer (in our case, zinc 4,5-octacarboxyphthalocyaninate) in a matrix of non-photoactive aluminum-containing MOFs. It is found that this allows nanomaterials to be obtained with a set concentration of the sensitizer, the molecules of which are incorporated into the matrix and are isolated in it. The material is shown to exhibit high photocatalytic activity in the oxidation of anthracene by atmospheric oxygen using a low-power (41 W) lamp to simulate sunlight.