1,4,8,11,15,18,22,25-octaoctylphthalocyanine | 110962-72-6

• 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: 1,4,8,11,15,18,22,25-octaoctylphthalocyanine
• 英文别名: 5,8,14,17,23,26,32,35-Octaoctyl-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；5,8,14,17,23,26,32,35-octaoctyl-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
• CAS: 110962-72-6
• 化学式: C₉₆H₁₄₆N₈
• 分子量: 1412.27
• InChiKey: DFLUNEJMQBIFBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  38.7
• 重原子数：
  104
• 可旋转键数：
  56
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4,8,11,15,18,22,25-octaoctylphthalocyanine 在 十二羰基三钌 作用下， 以 苯甲腈 为溶剂， 反应 1.67h， 以86%的产率得到carbonyl(1,4,8,11,15,18,22,25-octaoctylphthalocyaninato)ruthenium(II)
  参考文献：
  名称：

  Catalytic epoxidation of stilbenes with non-peripherally alkyl substituted carbonyl ruthenium phthalocyanine complexes

  摘要：

  通过金属插入 Ru3(CO)12 制备了一些新型羰基（1,4,8,11,15,18,22,25-八烷基酞菁）-钌（II）配合物。新化合物通过 1H NMR、13C NMR、IR、UV-vis 和质谱进行了表征。该研究表明，这类配合物，特别是羰基（1,4,8,11,15,18,22,25-八己基邻苯二甲酰）钌（II）和羰基[1,4,8,11,15,18,22、和羰基[1,4,8,11,15,18,22,25-八（2-环己基乙基）酞氰基]-钌（II）在以 2,6-二氯吡啶 N-氧化物为氧化剂的二苯乙烯环氧化反应中表现出较高的催化活性和稳定性。

  DOI：

  10.1142/s1088424612500459
• 作为产物：
  描述：

  3,6-dioctylphthalonitrile 在 甲基锂 、 溶剂黄146 作用下， 以 乙醚 、 环己醇 为溶剂， 反应 4.17h， 以35%的产率得到1,4,8,11,15,18,22,25-octaoctylphthalocyanine
  参考文献：
  名称：

  改进非外围烷基取代的四苯并三氮杂卟啉的合成

  摘要：

  摘要 对非外围烷基取代的大环分子 1,4,8,11,15,18,22,25-八烷基四苯并三氮杂卟啉 (CnTBTAPH2) 合成的改进进行了研究。在3,6-二烷基邻苯二甲腈到CnTBTAPH2的反应中，通过用甲基锂代替常规格氏试剂，产率得到显着提高。使用稳定溶剂的改进程序对于反应系统的放大以及产率的提高非常有效。

  DOI：

  10.1080/15421406.2017.1348802

文献信息

• Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles
  作者：Daniel J Tate、Rémi Anémian、Richard J Bushby、Suwat Nanan、Stuart L Warriner、and Benjamin J Whitaker

  DOI：10.3762/bjoc.8.14

  日期：——

  It has been shown that the base-initiated cyclo-oligomerisation of phthalonitriles is favoured by bulky α-substituents making it possible to obtain the metal-free phthalocyanine directly and in high yield. The phthalocyanine with eight α-isoheptyl substituents gives a high time-of-flight hole mobility of 0.14 cm²·V⁻¹·s⁻¹ within the temperature range of the columnar hexagonal phase, that is 169–189 °C.

  已经表明，邻苯二腈的碱性引发的环状寡聚反应受到庞大的α-取代基的偏爱，从而可以直接且高产率地获得无金属酞菁。具有八个α-异庚基取代基的酞菁在柱状六角相温度范围内（即169–189°C）具有高达0.14 cm²·V⁻¹·s⁻¹的飞行时间孔迁移率。
• Synthesis and characterization of some octaalkyl substituted lead phthalocyanines and unexpected variations in lead lability arising from the position of substituents and their chain length
  作者：Lydia X. Sosa-Vargas、Isabelle Chambrier、Colin J. MacDonald、Simon J. Coles、Graham J. Tizzard、Andrew N. Cammidge、Michael J. Cook

  DOI：10.1142/s108842461350020x

  日期：2013.6

  The preparation of some peripherally substituted (2,3,9,10,16,17,23,24) and non-peripherally substituted (1,4,8,11,15,18,22,25) octaalkyl lead(II) phthalocyanines with different alkyl chain lengths (6, 7, 8 or 9 carbons) is described and a comparison of some of their properties reported. X-ray structure analyses of the isomeric peripheral and non-peripheral octakis(octyl)phthalocyaninato lead(II) compounds reveal a greater degree of distortion of the ligand ring system from planarity in the former derivative. The series of peripherally substituted octaalkyl lead(II) phthalocyanines exhibit columnar liquid crystal behavior whereas the non-peripherally substituted isomers do not. The lability of the lead ion was investigated using ¹ H NMR spectrometry under a specific set of conditions (8.8 × 10^-4 M solutions of the phthalocyanine in d₈-toluene containing d₄-acetic acid 2.06 × 10^-5 M). All the compounds underwent acid catalyzed demetalation at rates dependent upon the location of the substituents and, more surprisingly, the chain length of the alkyl groups. Under these conditions the lead ion within each of the peripherally substituted octaalkyl lead phthalocyanines was more labile than that in the non-peripherally substituted isomer.

  本文介绍了一些外周取代（2,3,9,10,16,17,23,24）和非外周取代（1,4,8,11,15,18,22,25）、具有不同烷基链长度（6、7、8 或 9 个碳原子）的八烷基酞菁铅（II）的制备方法，并对它们的一些性质进行了比较。对同分异构的外周和非外周辛基酞菁族铅（II）化合物的 X 射线结构分析表明，前者衍生物中配体环系统的平面变形程度更大。外周取代的八烷基酞菁铅（II）系列表现出柱状液晶行为，而非外周取代的异构体则没有。在一组特定条件下（酞菁在含有 2.06 × 10-5 M d4-乙酸的 d8-甲苯中的 8.8 × 10-4 M 溶液），使用 1 H NMR 光谱法研究了铅离子的稳定性。所有化合物都在酸催化下发生了脱金属反应，脱金属的速度取决于取代基的位置，更令人惊讶的是取决于烷基的链长。在这些条件下，外周取代的八烷基酞菁铅中的铅离子比非外周取代的异构体中的铅离子更易变。
• Design and synthesis of liquid crystalline phthalocyanines: combinations of substituents that promote the discotic nematic mesophase
  作者：Andrew D. Garland、Isabelle Chambrier、Andrew N. Cammidge、Michael J. Cook

  DOI：10.1016/j.tet.2015.04.006

  日期：2015.9

  exhibit only columnar mesophases, which is common among liquid crystalline phthalocyanines. However, four examples form the rare discotic nematic mesophase. A general structural feature is deduced in that this rare phase is favoured when the number of linking atoms in the hydroxyalkyl chain exceeds twice the number of carbon atoms in any one of the six common alkyl chains, disrupting the columnar packing

  一个同源系列的十四个无金属的1,4,8,11,15,18-六（烷基）-22-甲基-25-羟烷基酞菁衍生物可询问六个烷基链和促进热致向列液晶行为的羟烷基链的长度。除两种化合物外，所有化合物均形成中间相。其余八种化合物仅表现出柱状中间相，这在液晶酞菁中很常见。然而，四个例子形成了罕见的盘状向列中间相。推断出一般的结构特征是，当羟烷基链中的连接原子数超过六个普通烷基链中任何一个的碳原子数的两倍时，这种稀有相是有利的，从而破坏了柱状堆积排列。此外，
• Thiophenotribenzoporphyrazines: novel near-IR absorbing dyes
  作者：Michael J. Cook、Ali Jafari-Fini

  DOI：10.1039/a607004c

  日期：——

  The first examples of thiophenotribenzoporphyrazines have been synthesised. The compounds obtained bear either six or eight alkyl chains and show Q-band absorptions which are red shifted relative to analogous phthalocyanine derivatives. Their formulations as spin coated films show broad band absorption extending into the near IR. The compounds exhibit discotic mesophase behaviour.

  噻吩三苯并紫菜嗪的第一个例子是 合成的。获得的化合物带有六个或八个烷基链 并显示 Q 波段吸收相对于类似的发生红移 酞菁衍生物。他们的旋涂薄膜配方显示 宽带吸收延伸至近红外区域。化合物表现出 盘状中间相行为。
• Self-assembled monolayers of phthalocyanine derivatives on glass and silicon
  作者：Michael J. Cook、Roxana Hersans、Jim McMurdo、David A. Russell

  DOI：10.1039/jm9960600149

  日期：——

  The synthesis of three phthalocyanine derivatives functionalised with seven or eight substituents including either one or two trichlorosilylalkyl chains is described. Self-assembled monolayers of the derivatives covalently bound to silicon and glass have been formed and characterised by FTIR and visible region spectroscopies.

  本文介绍了三种酞菁衍生物的合成过程，这些衍生物具有七个或八个取代基，其中包括一个或两个三氯硅烷基链。这些衍生物与硅和玻璃共价结合形成了自组装单层，并通过傅里叶变换红外光谱和可见光区光谱进行了表征。