1,4,8,11,15,22,25-octadecylphthalocyanine | 110962-74-8

• 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: 1,4,8,11,15,22,25-octadecylphthalocyanine
• 英文别名: 1,4,8,11,15,22,25-octadecyltetrabenzotriazaporphyrin；5,8,14,17,23,26,32,35-Octakis-decyl-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-octakis-decyl-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: 110962-74-8
• 化学式: C₁₁₂H₁₇₈N₈
• 分子量: 1636.7
• InChiKey: OIINSDUIWNPVKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  47.4
• 重原子数：
  120
• 可旋转键数：
  72
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  1,4,8,11,15,22,25-octadecylphthalocyanine 、 copper diacetate 以 戊醇 为溶剂， 以72%的产率得到1,4,8,11,15,18,22,25-octadecylphthalocyaninatocopper
  参考文献：
  名称：

  McKeown, Neil; Chambrier, Isabelle; Cook, Michael J., Journal of the Chemical Society. Perkin transactions I

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6-二癸基酞腈 在 戊醇 、 lithium 、 溶剂黄146 作用下， 以 戊醇 为溶剂， 反应 16.5h， 生成 1,4,8,11,15,22,25-octadecylphthalocyanine
  参考文献：
  名称：

  Synthesis and electrochemical characterisation of some long chain 1,4,8,11,15,18,22,25-octa-alkylated metal-free and zinc phthalocyanines possessing discotic liquid crystalline properties

  摘要：

  一系列长链（C10、C12、C15 和 C18）3,6-二烷基邻苯二甲酰亚胺经 4 个步骤由噻吩制备而成，并转化为标题酞菁的无金属锌衍生物。使用 1H NMR、MALDI-TOF ms 和溶液相电子（UV-VIS）光谱对对称大环进行了表征。在二氯甲烷或 1,2-二氯乙烷中，拥有较短烷基取代基的无金属大环的四个环基氧化还原过程的电位范围为-1.8 至 1.2 V vs. Ag/Ag+。随着 8 个烷基取代基链长的增加，可逆性变差。锌配合物的氧化还原过程不像无金属酞菁那样明确。所有化合物都表现出盘状热向性液晶行为，研究采用了偏光光学显微镜和差示扫描量热法（DSC）。最多可检测到三种不同的介相。与不含金属的化合物相比，锌衍生物在更高的温度下显示出液晶特性。无金属酞菁和带有 C12 链的锌酞菁的结晶到盘状液晶介相转变温度最低。在玻璃上浇铸的薄膜（厚度约为 1000 埃）的变温紫外-可见光谱中，获得了结晶、介相和各向同性液相化合物的光谱。各向同性液态薄膜的光谱与同一化合物溶液的光谱相似。

  DOI：

  10.1039/b006123i

文献信息

• Synthesis and electrochemical characterisation of some long chain 1,4,8,11,15,18,22,25-octa-alkylated metal-free and zinc phthalocyanines possessing discotic liquid crystalline properties
  作者：Jannie C. Swarts、Ernie H. G. Langner、Nina Krokeide-Hove、Michael J. Cook

  DOI：10.1039/b006123i

  日期：——

  A series of long chain (C10, C12, C15 and C18) 3,6-dialkylated phthalonitriles, prepared in 4 steps from thiophene, have been converted into the title phthalocyanines as metal-free and zinc derivatives. The symmetric macrocycles were characterised using 1H NMR, MALDI-TOF ms and solution phase electronic (UV-VIS) spectroscopy. Four ring-based redox processes for the metal-free macrocycles possessing shorter alkyl substituents could be identified in the potential range −1.8 to 1.2 V vs. Ag/Ag+ in dichloromethane or 1,2-dichloroethane. Reversibility became poorer with an increase in chain length of the eight alkyl substituents. The redox processes of the zinc complexes were not as well defined as those of the metal-free phthalocyanines. All compounds exhibited discotic thermotropic liquid crystal behaviour, which was studied using polarised optical microscopy and differential scanning calorimetry (DSC). Up to three different mesophases were detected. The zinc derivatives showed liquid crystalline behaviour at much higher temperatures than the metal-free compounds. The metal-free and zinc phthalocyanines with C12 chains had the lowest crystalline to discotic liquid crystalline mesophase transition temperatures. Variable temperature UV-VIS spectra of thin films (ca. 1000 Å thick) of the title compounds cast on glass were obtained for the compounds in the crystalline, meso- and isotropic liquid phase. The spectrum of a thin film of the isotropic liquid resembled the spectrum obtained from a solution of the same compound.

  一系列长链（C10、C12、C15 和 C18）3,6-二烷基邻苯二甲酰亚胺经 4 个步骤由噻吩制备而成，并转化为标题酞菁的无金属锌衍生物。使用 1H NMR、MALDI-TOF ms 和溶液相电子（UV-VIS）光谱对对称大环进行了表征。在二氯甲烷或 1,2-二氯乙烷中，拥有较短烷基取代基的无金属大环的四个环基氧化还原过程的电位范围为-1.8 至 1.2 V vs. Ag/Ag+。随着 8 个烷基取代基链长的增加，可逆性变差。锌配合物的氧化还原过程不像无金属酞菁那样明确。所有化合物都表现出盘状热向性液晶行为，研究采用了偏光光学显微镜和差示扫描量热法（DSC）。最多可检测到三种不同的介相。与不含金属的化合物相比，锌衍生物在更高的温度下显示出液晶特性。无金属酞菁和带有 C12 链的锌酞菁的结晶到盘状液晶介相转变温度最低。在玻璃上浇铸的薄膜（厚度约为 1000 埃）的变温紫外-可见光谱中，获得了结晶、介相和各向同性液相化合物的光谱。各向同性液态薄膜的光谱与同一化合物溶液的光谱相似。
• 1,4,8,11,15,18,22,25-Octa-alkyl phthalocyanines: new discotic liquid crystal materials
  作者：Michael J. Cook、Mervyn F. Daniel、Kenneth J. Harrison、Neil B. McKeown、Andrew J. Thomson

  DOI：10.1039/c39870001086

  日期：——

  Metal-free and copper(II) 1,4,8,11,15,18,22,25-octa-alkyl phthalocyanines have been prepared with alkyl chain lengths between C4 and C10; all except those with C4 and C5 chains show thermotropic liquid crystalline behaviour with one or more mesophases.

  已经制备了烷基链长度在C 4和C 10之间的无金属和铜的（II）1,4,8,11,15,18,22,25-八烷基酞菁；除具有C 4和C 5链的那些外，所有均显示具有一个或多个中间相的热致液晶行为。
• 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：——
• McKeown, Neil; Chambrier, Isabelle; Cook, Michael J., Journal of the Chemical Society. Perkin transactions I
  作者：McKeown, Neil、Chambrier, Isabelle、Cook, Michael J.

  DOI：——

  日期：——
• 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：——