tetrakis(2,3-dihydroxyphenyl)porphyrin | 88422-71-3

• 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: tetrakis(2,3-dihydroxyphenyl)porphyrin
• CAS: 88422-71-3
• 化学式: C₄₄H₃₀N₄O₈
• 分子量: 742.744
• InChiKey: QYIYZOUWBCCUNE-NTWARUPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.97
• 重原子数：
  56.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  219.2
• 氢给体数：
  10.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  zinc(II) acetate dihydrate 、 tetrakis(2,3-dihydroxyphenyl)porphyrin 以 甲醇 为溶剂， 以95%的产率得到zinc(II) tetrakis(2,3-dihydroxyphenyl)porphyrin
  参考文献：
  名称：

  使用具有邻苯二酚锚固基团的卟啉染料制备和分析染料敏化太阳能电池（DSSC）†

  摘要：

  本文中，我们报道了四种不同的锌（II）四（二羟基苯基）卟啉锌（ZnTDHPP）的制备和应用，它们是染料敏化太阳能电池（DSSCs）中的敏化染料。实验结果包括溶液和固态UV-Vis数据，稳态电流-电压特性，我们的理论分析包括密度泛函理论（DFT）和Langmuir等温吸附形式。结果表明，具有相邻羟基的Zn四（2,3-二羟基苯基）卟啉（Zn2,3TDHPP）和具有相邻羟基的Zn四（3,4-二羟基苯基）卟啉（Zn3,4TDHPP）比TiO 2表面更牢固地附着羧酸盐。邻苯二酚锚固基团显示出染料在TiO 2上的高稳定性表面。在几天后，由这些卟啉制备的细胞没有显示出染料从TiO 2表面的显着解吸。尽管在TiO 2表面负载的染料较少，但是基于Zn2,3TDHPP的DSSC在AM 1.5辐照下显示出最佳的光伏性能，与常规的Zn四（对-羧基苯基）卟啉（ZnTCPP）相当。然而，非合作OH键合的TiO 2为Zn2

  DOI：

  10.1039/c5ra23584g
• 作为产物：
  描述：

  meso-5,10,15,20-tetrakis(2,3-dimethoxyphenyl)porphyrin 在 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以80%的产率得到tetrakis(2,3-dihydroxyphenyl)porphyrin
  参考文献：
  名称：

  使用具有邻苯二酚锚固基团的卟啉染料制备和分析染料敏化太阳能电池（DSSC）†

  摘要：

  本文中，我们报道了四种不同的锌（II）四（二羟基苯基）卟啉锌（ZnTDHPP）的制备和应用，它们是染料敏化太阳能电池（DSSCs）中的敏化染料。实验结果包括溶液和固态UV-Vis数据，稳态电流-电压特性，我们的理论分析包括密度泛函理论（DFT）和Langmuir等温吸附形式。结果表明，具有相邻羟基的Zn四（2,3-二羟基苯基）卟啉（Zn2,3TDHPP）和具有相邻羟基的Zn四（3,4-二羟基苯基）卟啉（Zn3,4TDHPP）比TiO 2表面更牢固地附着羧酸盐。邻苯二酚锚固基团显示出染料在TiO 2上的高稳定性表面。在几天后，由这些卟啉制备的细胞没有显示出染料从TiO 2表面的显着解吸。尽管在TiO 2表面负载的染料较少，但是基于Zn2,3TDHPP的DSSC在AM 1.5辐照下显示出最佳的光伏性能，与常规的Zn四（对-羧基苯基）卟啉（ZnTCPP）相当。然而，非合作OH键合的TiO 2为Zn2

  DOI：

  10.1039/c5ra23584g

文献信息

• Electrochemical synthesis of novel π-extended phenoxazine derivatives of porphyrincatecholes
  作者：Samira Osati、Saied Saeed Hosseiny Davarani、Nasser Safari、Mohammad Hossein Banitaba

  DOI：10.1016/j.electacta.2011.08.030

  日期：2011.10

  intermolecular and intramolecular Michael addition reactions. Spectroscopic characterization and voltammetry results have allowed us to propose four independent ECEC mechanisms for the electrochemical oxidation pathway. The functionalization of the porphyrins affected their photophysical properties. Expansion of the UV–vis spectrum range and the decrease of the fluorescence intensity of the products would

  通过绿色一锅法合成了三种新的功能化苯恶嗪-邻苯二酚卟啉7a–c，并通过光谱分析对其结构进行了表征。在2-氨基苯酚8作为二齿亲核试剂的存在下，带有四个邻苯二酚单元的5,10,15,20-四（2,3-二羟基苯基）卟啉（1a–c）的电氧化反应已经完成，并且吩恶嗪环已经被氧化。由分子间和分子内迈克尔加成反应形成。光谱表征和伏安法结果使我们能够提出四个独立的ECEC电化学氧化途径的机理。卟啉的功能化影响了它们的光物理性质。紫外-可见光谱范围的扩大和产物荧光强度的降低将支持卟啉核心激发态与作为电子受体亚基的四个取代基之间的能量转移。SEM图像表明该方法产生具有立方纳米结构的规则形状的锰卟啉纳米颗粒7c。
• Hyperbranched polymers
  申请人：Twyman James Lance

  公开号：US20050113554A1

  公开（公告）日：2005-05-26

  A water-soluble hyperbranched polymer comprising a porphyrin moiety and one or more hyperbranched polymer chains covalently bound thereto. The polymer when metalated with an Fe(II) ion is capable of mimicking the oxygen binding properties of blood. The polymer may be used as a haemoglobin replacement, in synthetic blood products and as a blood substitute.

  一种水溶性的超支化聚合物，包含卟啉基团和一个或多个共价结合在其中的超支化聚合物链。当该聚合物与Fe（II）离子金属化后，能够模拟血液的氧结合特性。该聚合物可用作血红蛋白替代品，用于合成血液制品和作为血液替代品。
• Porphyrin Synthesis in Surfactant Solution:  Multicomponent Assembly in Micelles
  作者：Richard P. Bonar-Law

  DOI：10.1021/jo9600161

  日期：1996.1.1

  A synthesis of meso-substituted porphyrins in anionic sodium dodecyl sulfate micelles has been developed. Polar, functionalized aromatic aldehydes condense reversibly with pyrrole in the micellar phase. Oxidation of the porphyrinogen then provides functionalized porphyrins in yields of 10-48%. Hydrophobic aldehydes condense irreversibly to give low yields at practical substrate concentrations. Synthesis in D2O solution results in per-beta-deuterated porphyrins. A two-phase model is used to rationalize the dependence of porphyrin yield on reactant and surfactant concentration. Micelles are viewed as potential wells which promote porphyrinogen assembly by binding products more tightly than reactants.
• POTENCY AND SELECTIVE TOXICITY OF TETRA(HYDROXYPHENYL)- AND TETRAKIS(DIHYDROXYPHENYL)PORPHYRINS IN HUMAN MELANOMA CELLS, WITH AND WITHOUT EXPOSURE TO RED LIGHT
  作者：David A. James、Dennis P. Arnold、Peter G. Parsons

  DOI：10.1111/j.1751-1097.1994.tb05062.x

  日期：1994.4

  Abstract A series of tetra(hydroxyphenyl)‐(2‐, 3‐ and 4‐hydroxy; THPP) and tetrakis(dihydroxyphenyl)porphyrins (2,3‐, 2,4‐, 2,5‐, 3,4‐, and 3,5‐dihydroxy; TDHPP) was synthesized and tested for toxicity in HeLa cells and human melanoma cell lines. Irradiation of drug‐treated cells with >600 nm light greatly increased the toxicity of all drugs except the 2,5‐ and 3,5‐TDHPP. The THPP were more toxic than TDHPP in all cell lines, with or without irradiation; of the dihydroxy derivatives, the 3,4‐ and 2,4‐isomers were the most toxic and the 2,5‐isomer was the least toxic. The MM96E melanoma cell line, shown previously to be sensitive to hydrogen peroxide and superoxide ion, was not hypersensitive to killing by any of the above agents. HeLa cells, which lacked glutathione‐S‐transferase activity, were sensitive to the 4‐ and 2,3‐isomers after irradiation; similar amounts of all drugs were taken up by HeLa cells. The pigmented melanoma cell line MM418, resistant to UV‐B and in situ‐generated hydrogen peroxide but sensitive to glutathione (GSH) depletion, was found to be resistant to the 2,3‐isomer (no irradiation) and sensitive to the 3,4‐isomer. The results indicate that (1) phototoxicity in these phenylporphyrins is not mediated by superoxide ions or hydroxyl radicals, (2) toxicity is dependent on the orientation of the hydroxy groups, (3) GSH transferase and possibly GSH itself offer protection from the 4‐ and 3,4‐derivatives, respectively, and (4) the 3,4‐derivative and analogues of similar selectivity should be evaluated further for the treatment of primary melanoma.
• Semeikin, A. S.; Koifman, O. I.; Nikitina, G. E., Journal of general chemistry of the USSR, 1984, vol. 54, # 7, p. 1423 - 1426
  作者：Semeikin, A. S.、Koifman, O. I.、Nikitina, G. E.、Berezin, B. D.

  DOI：——

  日期：——