2,3,9,10,16,17,23,24-Octakis(pentyloxy)phthalocyanine | 130996-06-4

• 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-Octakis(pentyloxy)phthalocyanine
• 英文别名: 2,3,9,10,16,17,23,24-octakis(n-pentyloxy)phthalocyanine；H2Pc(OC5H11)8；6,7,15,16,24,25,33,34-octapentoxy-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),20,22,24,26,28,30(37),31,33,35-nonadecaene
• CAS: 130996-06-4
• 化学式: C₇₂H₉₈N₈O₈
• 分子量: 1203.62
• InChiKey: FQINWTHRYRTAKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.5
• 重原子数：
  88
• 可旋转键数：
  40
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  183
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,3,9,10,16,17,23,24-Octakis(pentyloxy)phthalocyanine 、 氯化二乙基铝 以 二氯甲烷 为溶剂， 生成 aluminium octa(pentoxy)phthalocyanine chloride
  参考文献：
  名称：

  Aluminum and lithium octa(pentoxy)phthalocyanine radicals

  摘要：

  A lithium phthalocyanine radical and the analogous aluminum phthalocyanine radical were synthesized as part of an investigation of isostructural dopants. An improved synthesis of the free base of octa(pentoxy)phthalocyanine (H2Pc*) involves the reduction of 1,2-dicyano-4,5-dipentoxybenzene with hydroquinone. Deprotonation with lithium bis(trimethylsilyl)amide leads to the dilithium derivative Li2Pc* and subsequent oxidation with ferrocenium yields the radical LiPc*. Treatment of H2Pc* with Et2AlCl gives ClAlPc* and reduction with sodium amalgam yields AlPc*, the first reported aluminum phthalocyanine radical. In the solid state LiPc* and AlPc* are electrical conductors with pressed-pellet conductivities of 8 x 10(-11) Omega(-1) cm(-1) and 5 x 10(-7) Omega(-1) cm(-1), respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2005.06.021
• 作为产物：
  描述：

  1,2-Dibromo-4,5-bis(pentyloxy)benzene 在 苄基三乙基氯化铵 、 lithium 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.25h， 生成 2,3,9,10,16,17,23,24-Octakis(pentyloxy)phthalocyanine
  参考文献：
  名称：

  Hanack, Michael; Guel, Ahmet; Hirsch, Andreas, Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 187, p. 365 - 382

  摘要：

  DOI：

文献信息

• Dysprosium Heteroleptic Corrole-Phthalocyanine Triple-Decker Complexes: Synthesis, Crystal Structure, and Electrochemical and Magnetic Properties
  作者：Guifen Lu、Cheng He、Kang Wang、Junshan Sun、Dongdong Qi、Lei Gong、Chiming Wang、Zhongping Ou、Sen Yan、Suyuan Zeng、Weihua Zhu

  DOI：10.1021/acs.inorgchem.7b01060

  日期：2017.10.2

  Two triple-decker dinuclear sandwich dysprosium complexes, which are represented as Dy2[Pc(OC5H11)8]2[Cor(FPh)3] (1) and Dy2[Pc(OC5H11)8]2[Cor(ClPh)3] (2), were synthesized and characterized by spectroscopic and electrochemical methods in nonaqueous media. Their electronic structures were also investigated on the basis of TD-DFT calculations. The sandwich triple-decker nature with the molecular conformation

  两个三层双核夹心络合物，分别表示为Dy 2 [Pc（OC 5 H 11）8 ] 2 [Cor（FPh）3 ]（1）和Dy 2 [Pc（OC 5 H 11）8 ] 2合成[Cor（ClPh）3 ]（2），并通过光谱和电化学方法在非水介质中表征。还根据TD-DFT计算对它们的电子结构进行了研究。分子结构为[Pc（OC 5 H 11）的三明治三层性质通过单晶X射线衍射分析清楚地显示了化合物1的8 ] Dy [Cor（FPh）3 ] Dy [Pc（OC 5 H 11）8 ]，并显示每个离子被异吲哚和吡咯氮八配位酞菁外环和中心Corrole环的原子。另外，两种化合物的磁性能也已被表征用于探索这些类型的三层复合物的功能。
• Quintuple-Decker Heteroleptic Phthalocyanine Heterometallic Samarium–Cadmium Complexes. Synthesis, Crystal Structure, Electrochemical Behavior, and Spectroscopic Investigation
  作者：Chao Liu、Wei Yang、Yuexing Zhang、Jianzhuang Jiang

  DOI：10.1021/acs.inorgchem.0c02816

  日期：2020.12.7

  compounds, (Pc)Sm(Pc)Cd(Pc*)Cd(Pc)Sm(Pc)} (1) and (Pc)Sm(Pc*)Cd(Pc*)Cd(Pc*)Sm(Pc)} (2), together with one homoleptic phthalocyanine species, (Pc*)Sm(Pc*)Cd(Pc*)Cd(Pc*)Sm(Pc*)} (3), were successfully fabricated, where H2Pc and H2Pc* represent unsubstituted phthalocyanine and 2,3,9,10,16,17,23,24-octakis(n-pentyloxy)phthalocyanine, respectively. Their quintuple-decker structures have been disclosed

  一锅法合成方法用于获得多种五层-酞菁酞菁异金属镧系元素-镉络合物。通过使用双层均相/杂合酞菁sa化合物与无金属酞菁和乙酸镉在1,2,4-三氯苯中在200°C下的反应，生成了两种新型的五层酞菁酞菁杂金属sa-镉化合物， （Pc）Sm（Pc）Cd（Pc *）Cd（Pc）Sm（Pc）}（1）和（Pc）Sm（Pc *）Cd（Pc *）Cd（Pc *）Sm（Pc）}（2），连同一种均化酞菁类物质，成功制备了（Pc *）Sm（Pc *）Cd（Pc *）Cd（Pc *）Sm（Pc *）}（3），其中H 2 Pc和H 2Pc *分别代表未取代的酞菁和2,3,9,10,16,17,23,24-辛基（正戊氧基）酞菁。它们的五重双层结构已经通过各种光谱技术和单晶X射线衍射公开。另外，这三种五重-十烷基复合物的价互变异构化已经通过加入苯氧噻啶六氯锑酸酯实现，产生了三种氧化形式，包括一，二和三电子氧化产物。从
• Cerium-promoted formation of metal-free phthalocyanines
  作者：Chi-Hang Lee、Dennis K.P Ng

  DOI：10.1016/s0040-4039(02)00756-6

  日期：2002.6

  Treatment of phthalonitriles with 6 mol% Of CeCl3 or Ce(acac)(3) (acac = acetylacetonate) in refluxing 1-pentanol affords the corresponding metal-free phthalocyanines in moderate yields. This non-alkaline pathway is complementary to the base-promoted cyclization methods which are commonly employed in the synthesis of phthalocyanines. Addition of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) greatly shortens the reaction time and increases the yield of these reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Novel Pathway to Synthesize Unsymmetrical 2,3,9,10,16,17,23-heptakis(alkoxyl)-24-mono(dimethylaminoalkoxyl)phthalocyanines
  作者：Zhaopin Bai、Yingning Gao、Peihua Zhu、Yongzhong Bian、Jianzhuang Jiang

  DOI：10.1021/ic101362y

  日期：2010.10.4

  A new pathway by means of transetherification has been developed to synthesize novel unsymmetrical 2,3,9,10,16, 17,23-heptakis(alkoxyl)-24-mono(dimethylaminoalkoxyl)phthalocyanine compounds. Cyclic tetramerization of 4,5-di-(alkoxyl)phthalonitrile in refluxing dimethylamino-alcohol with high boiling point such as dimethylaminoethanol (DMAE) and 1-dimethylamino-2-propanol in the presence of lithium and pyrazino[2,3-f}[1,10]phenanthroline-2,3-dicarbonitrile followed by treatment with acetic acid led to the isolation of a series of unsymmetrical metal free 2,3,9,10,16,17,23-heptakis(alkoxyl)-24-mono(dimethylaminoalkoxyl)phthalocyanine compounds H(2)Pc(OR)(7)[OR'N(CH(3))(2)]} [R = C(4)H(9), C(5)H(11), C(8)H(17) and R' = C(2)H(4); R C(4)H(9) and R' = CH(CH(3))CH(2)] (1-4), Metal insertion into unsymmetrical metal free phthalocyanines (Pc's) using Cu(Ac)(2). H(2)O in dimethylformamide (DMF) at 140 degrees C easily afforded corresponding unsymmetrical phthalocyaninato copper complexes CuPc(OR)(7)[OR'N(CH(3))(2)]} (5-8) in good yields. These novel unsymmetrical phthalocyanine compounds have been characterized by a series of spectroscopic methods including (1)H NMR, electronic absorption, IR, and mass spectroscopy in addition to elemental analysis. Their electrochemistry was also studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods. The present result will be helpful for designing and preparing unsymmetrical phthalocyanines with potential applications in dye-sensitized solar cells.
• Hanack, Michael; Guel, Ahmet; Hirsch, Andreas, Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 187, p. 365 - 382
  作者：Hanack, Michael、Guel, Ahmet、Hirsch, Andreas、Mandal, Braja K.、Subramanian, L. R.、Witke, Elisabeth

  DOI：——

  日期：——