1,4,8,11,15,18-hexabutoxy-23-[3-(hydroxymethyl)phenoxy]phthalocyanine | 1201171-05-2

• 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: 1,4,8,11,15,18-hexabutoxy-23-[3-(hydroxymethyl)phenoxy]phthalocyanine
• 英文别名: 1,4,5,8,9,12-hexabutoxy-14-[3-(hydroxymethyl)phenoxy]phtalocyanine；B6PH；[3-[(14,17,23,26,32,35-Hexabutoxy-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(37),3,5,7,9,11,13,15,17,19(39),20,22,24,26,28(38),29,31,33,35-nonadecaen-6-yl)oxy]phenyl]methanol；[3-[(14,17,23,26,32,35-hexabutoxy-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(37),3,5,7,9,11,13,15,17,19(39),20,22,24,26,28(38),29,31,33,35-nonadecaen-6-yl)oxy]phenyl]methanol
• CAS: 1201171-05-2
• 化学式: C₆₃H₇₂N₈O₈
• 分子量: 1069.31
• InChiKey: PZPBOCOUXGNOIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  79
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  194
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  单叔丁基琥珀酸酯 、 1,4,8,11,15,18-hexabutoxy-23-[3-(hydroxymethyl)phenoxy]phthalocyanine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以100%的产率得到1,4,8,11,15,18-hexabutoxy-23-[3-(tert-butylsuccinatoxymethyl)phenoxy]phthalocyanine
  参考文献：
  名称：

  Mono-, bis- and tetrahydroxy phthalocyanines as building blocks for monomolecular layer assemblies

  摘要：

  我们已经开发出三种基本的酞菁结构，分别含有一个、两个或四个羟基，它们易于合成和纯化，并能通过核磁共振和质谱进行表征。这些结构单元可以很容易地进一步修饰成锚基团，从而使分子适合附着在固体底物上。我们使用了硫代乙酸酯和五氟苯基酯，使目标酞菁能够在金、金属氧化物和玻璃上进行自组装。根据层的吸光度计算出的键合密度表明，平均分子面积在 1-3 nm2 之间，这可以通过侧取代基和连接体的数量进行部分控制。

  DOI：

  10.1142/s1088424610002185
• 作为产物：
  描述：

  4-[3-(hydroxymethyl)phenoxy]phthalonitrile 、 3,6-二丁氧基-1,2-苯二甲腈 在 lithium 、 正丁醇 作用下， 反应 4.0h， 以24%的产率得到1,4,8,11,15,18-hexabutoxy-23-[3-(hydroxymethyl)phenoxy]phthalocyanine
  参考文献：
  名称：

  Mono-, bis- and tetrahydroxy phthalocyanines as building blocks for monomolecular layer assemblies

  摘要：

  我们已经开发出三种基本的酞菁结构，分别含有一个、两个或四个羟基，它们易于合成和纯化，并能通过核磁共振和质谱进行表征。这些结构单元可以很容易地进一步修饰成锚基团，从而使分子适合附着在固体底物上。我们使用了硫代乙酸酯和五氟苯基酯，使目标酞菁能够在金、金属氧化物和玻璃上进行自组装。根据层的吸光度计算出的键合密度表明，平均分子面积在 1-3 nm2 之间，这可以通过侧取代基和连接体的数量进行部分控制。

  DOI：

  10.1142/s1088424610002185

文献信息

• Photoinduced electron transfer of double-bridged phthalocyanine–fullerene dyads
  作者：Marja Isosomppi、Nikolai V. Tkachenko、Alexander Efimov、Heidi Vahasalo、Johanna Jukola、Pirjo Vainiotalo、Helge Lemmetyinen

  DOI：10.1016/j.cplett.2006.08.107

  日期：2006.10

  phthalocyanine–fullerene dyads were studied with spectroscopic and electrochemical methods. The two-linker strategy was applied for the first time to phthalocyanine–fullerene dyads. Photoinduced electron transfer (ET) of the dyads was found to occur from the excited state of phthalocyanine both in polar and non-polar environment. Examination of ET energetics revealed that the phthalocyanine–fullerene dyads exist mainly

  用光谱和电化学方法研究了三种新的双桥酞菁-富勒烯二元化合物。双向连接策略首次应用于酞菁-富勒烯二元化合物。研究发现，在极性和非极性环境中，酞菁的激发态都发生了二元组的光诱导电子转移（ET）。ET高能学研究表明，与类似的双桥卟啉-富勒烯二联体常见的面对面取向相反，酞菁-富勒烯二联体主要存在于扩展构象中。
• Photoinduced vectorial electron transfer in multilayered Langmuir-Blodgett films of porphyrin and phtalocyanine derivatives
  作者：A. S. Alekseev、N. V. Tkachenko、A. V. Efimov、H. Lemmetyinen

  DOI：10.1134/s0036024410070253

  日期：2010.1

  A series of new phtalocyanines and phtalocyanine-fullerene dyads was synthesized. The dyads were transferred to solid substrates in the form of the Langmuir-Blodgett films. Poly(hexylthiophene) (PHT) and/or phtalocyanine (B6PH) were used as secondary electron donors in the multilayered structures, together with molecules of phtalocyanine-fullerene (B6PF) or porphyrin-fullerene (DHD6ee) dyads in a matrix of octadecylamine (ODA) molecules in a ratio of 1: 9. Directed photoinduced electron transfer in films was studied by means of the time-resolved Maxwell displacement charge method. It was established that the addition of a monolayer of molecules of the secondary B6PH donor to a monolayer of molecules of the DHD6ee/ODA (1: 9) dyad resulted in a thirty-fold increase in the sample's photovoltaic response; it did not, however, change the recombination rate of the charges as compared to a single monolayer of the dyad molecules. In the case of bilayer samples consisting of B6PF/ODA (1: 9) and PHT/ODA (3: 2) monolayers, both quantities increased. The absorption of visible light over a wide spectral range was achieved via the use of three-component (PHT, B6PH and DHD6ee) multilayered structures. The relative sensitivities of the samples to excitation radiation were assessed and the efficiencies of their transformation of light energy to electric potential were compared. The largest sensitivity values were obtained for three-component samples prepared from PHT, B6PH, and DHD6ee monolayers in which the sensitivity value was 500 times larger than that for a separate monolayer of DHD6ee dyad molecules.
• Mono-, bis- and tetrahydroxy phthalocyanines as building blocks for monomolecular layer assemblies
  作者：Essi Sariola、Anne Kotiaho、Nikolai V. Tkachenko、Helge Lemmetyinen、Alexander Efimov

  DOI：10.1142/s1088424610002185

  日期：2010.5

  We have developed three basic phthalocyanine structures, containing one, two, or four hydroxy groups, which are simple to synthesize and purify, as well as can be characterized well by NMR and MS. These building blocks can easily be further modified to have anchor groups, which make the molecules suitable for attachment to solid substrates. We have used thioacetate and pentafluorophenyl ester moieties, giving target phthalocyanines the ability to self-assemble on gold, metal oxides, and glass. Bonding densities calculated from the absorbances of the layers suggest mean molecular area to be in the range of 1–3 nm², which can be partially controlled by side substituents and the number of linkers.

  我们已经开发出三种基本的酞菁结构，分别含有一个、两个或四个羟基，它们易于合成和纯化，并能通过核磁共振和质谱进行表征。这些结构单元可以很容易地进一步修饰成锚基团，从而使分子适合附着在固体底物上。我们使用了硫代乙酸酯和五氟苯基酯，使目标酞菁能够在金、金属氧化物和玻璃上进行自组装。根据层的吸光度计算出的键合密度表明，平均分子面积在 1-3 nm2 之间，这可以通过侧取代基和连接体的数量进行部分控制。