2,3,9,10,16,17,23-heptakis(n-octyloxy)-24-mono(dimethylaminoethyloxy)phthalocyanine | 1246762-27-5

• 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-heptakis(n-octyloxy)-24-mono(dimethylaminoethyloxy)phthalocyanine
• 英文别名: H2{Pc(OC8H17)7[OC2H4N(CH3)2]}；2-[(7,15,16,24,25,33,34-heptaoctoxy-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(40),4,6,8,10,12(39),13,15,17,19,21,23,25,27,30(37),31,33,35-nonadecaen-6-yl)oxy]-N,N-dimethylethanamine
• CAS: 1246762-27-5
• 化学式: C₉₂H₁₃₉N₉O₈
• 分子量: 1499.17
• InChiKey: UYYMKVCJXWPOMR-UHFFFAOYSA-N

物化性质

• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  30.1
• 重原子数：
  109
• 可旋转键数：
  60
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  186
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  二甲氨基甲醇 、 4,5-二辛氧基-1,2-苯二甲腈 、 吡嗪并[2,3-f][1,10]菲罗啉-2,3-二甲腈 在 lithium 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以29%的产率得到2,3,9,10,16,17,23,24-八辛氧基-29H,-31H-酞菁染料
  参考文献：
  名称：

  Novel Pathway to Synthesize Unsymmetrical 2,3,9,10,16,17,23-heptakis(alkoxyl)-24-mono(dimethylaminoalkoxyl)phthalocyanines

  摘要：

  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 Cu{Pc(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.

  DOI：

  10.1021/ic101362y

文献信息

• 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.