3,6-dipentylphthalonitrile | 128912-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-dipentylphthalonitrile
• 英文别名: 3,6-bis(pentyl)phthalonitrile；3,6-dipentylbenzene-1,2-dicarbonitrile
• CAS: 128912-47-0
• 化学式: C₁₈H₂₄N₂
• 分子量: 268.402
• InChiKey: NFNOARKXRAYADQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.58
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,6-dipentylphthalonitrile 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23%的产率得到1,4,8,11,15,18,22,25-Octaisopentylphthalocyanine
  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
• 作为产物：
  描述：

  3,6-二羟基邻苯二甲腈 在 2,6-二甲基吡啶 、 bis(triphenylphosphine)nickel(II) chloride 、 正丁基锂 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 3,6-dipentylphthalonitrile
  参考文献：
  名称：

  一些 3,6-二取代邻苯二甲腈的路线和从中衍生的酞菁实例：概述

  摘要：

  本文回顾了一些合成途径，这些途径提供了 3,6-二取代酞腈，这是合成 1,4,8,11,15,18,22,25-八取代酞菁衍生物的前体。评价了使用 Diels-Alder 反应合成 3,6-二烷基、3,6-二烷氧基甲基、3,6-二烯基和 3,6-二苯基邻苯二甲腈的早期路线。然而，审查的重点集中在 2,3-二氰基氢醌作为获得 3,6-二取代邻苯二甲腈的起始原料的范围和应用。使用 2,3-二氰基氢醌的最早例子涉及其 O-烷基化以提供 3,6-二烷氧基邻苯二甲腈。这些是近红外吸收酞菁衍生物的直接前体。2,3-二氰基氢醌的三氟甲磺酸化扩展了该化合物用于合成酞菁的范围；ñAr 反应并容易与硫醇反应生成 3,6-双（烷基硫烷基）和 3,6-双（芳基硫烷基）邻苯二甲腈。3,6-双（苯基硒基）邻苯二甲腈最近也从相同的前体中获得。从中获得的酞菁衍生物通常表现出强烈的红移 Q 波段吸收，该吸收对中心金属离子特别敏感。2

  DOI：

  10.1142/s108842461330005x

文献信息

• Liquid crystalline properties of unsymmetrically substituted phthalocyanines: structural features leading to nematic mesophase materials
  作者：Andrew D. Garland、Geoffrey C. Bryant、Isabelle Chambrier、Andrew N. Cammidge、Michael J. Cook

  DOI：10.1142/s1088424614500722

  日期：2014.10

  A novel homologous series of four 1,4,8,11,15,18-hexakis(pentyl)-22-methyl-25-hydroxyalkylphthalocyanine derivatives with the hydroxyalkyl chain varying from hydroxynonyl through to hydroxydodecyl has been synthesized to investigate the role of the hydroxyalkyl chain in promoting thermotropic liquid crystalline behavior. Polarizing optical miscoscopy reveals that the compound with the shortest hydroxyalkyl chain (hydroxynonyl) exhibits a mesophase with a texture characteristic of a columnar mesophase, common among liquid crystalline phthalocyanine derivatives. However, as the chain is lengthened along the series, there appears a second type of mesophase that shows a schlieren texture. Such a texture is characteristic of a nematic phase and rare among liquid crystalline phthalocyanine derivatives. A fifth compound, the novel 1,4,8,11,15,18-hexakis(pentyl)-22-methyl-25-dodecylphthalocyanine, exhibits only columnar mesophase behavior suggesting that the hydroxyl group at the end of the longer chains of the former compounds is important in developing the nematic phase.

  为了研究羟基烷基链在促进热致性液晶行为中的作用，我们合成了四种 1,4,8,11,15,18-六（戊基）-22-甲基-25-羟基烷基酞菁衍生物的新型同源系列，其羟基烷基链从羟基壬基到羟基十二烷基不等。偏振光学镜检显示，羟烷基链最短的化合物（羟基壬基）显示出具有柱状介相特征的介相，这在液晶酞菁衍生物中很常见。然而，当链沿系列加长时，就会出现第二种类型的介相，表现出雪莲纹理。这种纹理是向列相的特征，在液晶酞菁衍生物中十分罕见。第五种化合物，即新型 1,4,8,11,15,18-六（戊基）-22-甲基-25-十二烷基酞菁，仅表现出柱状介相行为，这表明前一种化合物较长链末端的羟基对形成向列相非常重要。
• Predominant effect of connecting atom and position of substituents on azomethine nitrogens’ basicity in phthalocyanines
  作者：Antonin Cidlina、Jan Svec、Lucie Ludvová、Jiří Kuneš、Petr Zimcik、Veronika Novakova

  DOI：10.1142/s1088424616500747

  日期：2016.8

  trapped hydrogen at azomethine nitrogen via hydrogen bonding and van der Waals interactions, respectively. The basicity of [Formula: see text]-series clearly correlated with the electronic effects of substituents.1H NMR studies confirmed the possibility of the weak bonding interactions in [Formula: see text]-alkyloxy and [Formula: see text]-alkylsulfanyl Pcs, however, the position of the1H NMR signal

  在一系列取代基位置不同的酞菁 (Pcs) 上研究了偶氮甲碱氮的碱度，[公式：见正文]外围（[公式：见正文]-系列）和非外围取代的 Pcs（[公式：见正文]-系列），以及一种取代基（烷基硫烷基、烷氧基或烷基）。通过亲核取代或 Negishi 偶联制备合适的 3,6-或 4,5-二取代邻苯二甲腈。目标锌Pcs采用Linstead法合成。碱度采用吸收法研究1用三氟乙酸滴定后，氯仿中的 H NMR 光谱。平衡常数（log [公式：见正文]）表明系列内有显着差异。碱度降低如下： [分子式：见正文]-烷氧基 ≫ [分子式：见正文]-烷硫基 > [分子式：见正文]-烷氧基 > [分子式：见正文]-烷基 > [分子式：见正文]-烷硫基 ∼ [公式：见正文]-log [公式：见正文]高于 7 至 2.6 M [公式：见正文]的烷基。[分子式：见正文]-烷氧基和 [分子式：见正文]-烷基硫烷基 Pcs 的碱度
• McKeown, Neil B.; Chambrier, Isabelle; Cook, Michael J., Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1169 - 1177
  作者：McKeown, Neil B.、Chambrier, Isabelle、Cook, Michael J.

  DOI：——

  日期：——
• Study of Substituent Effects on the Photoconductivity of Soluble 2,(3)- and 1,(4)-Substituted Phthalocyaninato- and Naphthalocyaninatotitanium(IV) Oxides
  作者：Götz Winter、Heino Heckmann、Peter Haisch、Wolfgang Eberhardt、Michael Hanack、Larry Lüer、Hans-Joachim Egelhaaf、Dieter Oelkrug

  DOI：10.1021/ja981644y

  日期：1998.11.1

  Soluble alkyl (II, 8a,b), fluoroalkyl,(4a), and fluoroalkoxy (4b,c, 8c) 1,(4)- or 2,(3)-substituted phthalocyaninato- and linear 2,(3)- and-angular 1,(2)-annulated naphthalocyaninatotitanium(IV) oxides 10, 12, and 14 were synthesized and characterized with regard to their spectroscopic, photophysical, and photochemical properties. While alkyl- and fluoroalkoxy-substituted compounds are highly soluble in nonpolar solvents, e.g., hexane, fluoroalkyl-substituted compounds are better soluble in polar aprotic solvents such as acetone. The stability against photooxidation in solution is' enhanced on going-from alkylated phthalocyanines 1,(4)-(C(5)H(11))(8)PcTiO (8a), 1,(4)-(C(6)H(13))(8)PcTiO (4b), and 2,(3)-(C(4)H(9))(8)PcTiO (II) to fluorinated phthalocyanines 2,(3)-(CF(3))(4)PcTiO (4a), 2,(3)-(CF(3)CH(2)O)(4)PcTiO (4b), and 2,(3)-(CF(3)CH(2)O)(8)PcTiO (4c), from phthalocyanines to naphthalocyanines (tert-butyl)(4)-2,(3)-NcTiO (10), 1,(2)-NcTiO (12), and (tert-butyl)(4)-1,(2)-NdTiO (14), and on going from 2,(3)-substituted 4a-c to 1,(4)-substituted phthalocyanines 8a-c. Thin films of these compounds, prepared by either vacuum deposition or spin casting, are classified into three types according to increasing intermolecular pi-pi interactions. Type alpha films, characterized:by absence of exciton splitting, are formed from 1,(4)-substituted phthalocyanines 8a-c. These films show low dark conductivities and photoconductivities and are considerably sensitive to photooxidation. Type beta films, characterized by weak exciton splitting, are formed from fluorinated phthalocyanines 4a-c as well as from rapidly deposited 2,(3)-substituted phthalocyanines II and the unsubstituted PcTiO (I). These films show enhanced photoconductivity and are generally more stable against photooxidation than type alpha films. Type gamma films, formed by slow deposition of II, 10 and unsubstituted phthalocyanine I, are classified by a largely red-shifted B-band absorbing in the near-IR. These films are highly photosensitive as well as stabilized against photooxidation. Steady-state photoconductivities and dark conductivities in thin films are strongly dependent on oxygen partial pressure. Alkylated PcTiO's such as 8a, 8b, and II are found to be p-type conductors (positive oxygen influence on conductivities) like unsubstituted PcTiO (I), whereas angularly annulated naphthalocyanines such as 12 and 14 as well as fluorinated PcTiO's 4a-c are n-type conductors (negative oxygen influence on conductivity). These findings are rationalized by comparison with experimental and theoretical literature data.
• MCKEOWN, NEIL B.;CHAMBRIER, ISABELLE;COOK, MICHAEL J., J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 1169-1177
  作者：MCKEOWN, NEIL B.、CHAMBRIER, ISABELLE、COOK, MICHAEL J.

  DOI：——

  日期：——