1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide | 244780-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide
• 英文别名: 8,17-Dihydroxy-11,14,22,26-tetraphenoxy-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),7,9,11,13,15,17,20,23-dodecaene-6,19-dione；8,17-dihydroxy-11,14,22,26-tetraphenoxy-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),7,9,11,13,15,17,20,23-dodecaene-6,19-dione
• CAS: 244780-86-7
• 化学式: C₄₈H₂₆N₂O₈
• 分子量: 758.743
• InChiKey: LPOLSWYSAJWIQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  58
• 可旋转键数：
  8
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N,N'-Di(tert-butoxycarbonyl)-1,6,7,12-tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures

  摘要：

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.

  DOI：

  10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w
• 作为产物：
  描述：

  1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisanhydride 在 乙酸铵 作用下， 以 丙酸 为溶剂， 反应 16.0h， 生成 1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures

  摘要：

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.

  DOI：

  10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

文献信息

• Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures
  作者：Frank Würthner、Christoph Thalacker、Armin Sautter、Wolfgang Schärtl、Wolfram Ibach、Olaf Hollricher

  DOI：10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

  日期：2000.11.3

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.