N,N'-dibutyl-1,6,7,12-tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide | 272445-56-4

• 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: N,N'-dibutyl-1,6,7,12-tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide
• 英文别名: N,N′-butyl-3,4,9,10-perylene diimide-1,6,7,12-phenoxy；PDIB-4OPh；7,18-Dibutyl-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),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• CAS: 272445-56-4
• 化学式: C₅₆H₄₂N₂O₈
• 分子量: 870.958
• InChiKey: FTQUPYTVZMBREQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  66
• 可旋转键数：
  14
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-dibutyl-1,6,7,12-tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以50%的产率得到5,6,12,13-tetraphenoxy-1,3,8,10-tetrahydro-2,9-dibutyl-2,9-diazadibenzo[cd,lm]perylene
  参考文献：
  名称：

  Substituted Diazadibenzoperylenes: New Functional Building Blocks for Supramolecular Chemistry

  摘要：

  DOI：

  10.1002/(sici)1521-3773(20000403)39:7<1243::aid-anie1243>3.0.co;2-z
• 作为产物：
  描述：

  1,6,7,12-四氯-3,4,9,10-苝四甲酸二酐 在 N-甲基吡咯烷酮 、 potassium carbonate 、 丙酸 作用下， 反应 24.0h， 生成 N,N'-dibutyl-1,6,7,12-tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Synthesis of Diazadibenzoperylenes and Characterization of Their Structural, Optical, Redox, and Coordination Properties

  摘要：

  Tetraphenoxy-substituted diazadibenzoperylenes 5a,b were synthesized from tetrachloroperylene tetracarboxylic acid bisanhydride I through imidization with benzylamine, nucleophilic displacement of the four chlorine atoms by phenolates, carbonyl group reduction by LiAlH4/AlCl3, and subsequent Pd/C-promoted debenzylation-dehydrogenation. The structural properties of these extended diazaarenes are discussed on the basis of a X-ray crystal structure of the N,N'-dibutylated diazadibenzoperylenium dication 6, which revealed a 25degrees twist of the central six-membered ring leading to an atropisomeric pi-conjugated backbone. The chromophoric systems of 5 and 6 were characterized by optical absorption and fluorescence spectroscopy, which revealed an intense fluorescence with a quantum yield of 75% for 5 and 50% for 6. Cyclic voltammetry showed reversible oxidation and reduction waves for 6, whereas the oxidation of 5 afforded the irreversible deposition of a conductive film on the electrode surface. Finally, the potential use of ligands 5 in supramolecular chemistry has been evaluated by complexation experiments with carboxylic acids and zinc tetraphenylporphyrin (ZnTPP).

  DOI：

  10.1021/jo011133l

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.
• Substituted Diazadibenzoperylenes: New Functional Building Blocks for Supramolecular Chemistry
  作者：Frank Würthner、Armin Sautter、Christoph Thalacker

  DOI：10.1002/(sici)1521-3773(20000403)39:7<1243::aid-anie1243>3.0.co;2-z

  日期：2000.4.3
• Synthesis of Diazadibenzoperylenes and Characterization of Their Structural, Optical, Redox, and Coordination Properties
  作者：Frank Würthner、Armin Sautter、Joachim Schilling

  DOI：10.1021/jo011133l

  日期：2002.5.1

  Tetraphenoxy-substituted diazadibenzoperylenes 5a,b were synthesized from tetrachloroperylene tetracarboxylic acid bisanhydride I through imidization with benzylamine, nucleophilic displacement of the four chlorine atoms by phenolates, carbonyl group reduction by LiAlH4/AlCl3, and subsequent Pd/C-promoted debenzylation-dehydrogenation. The structural properties of these extended diazaarenes are discussed on the basis of a X-ray crystal structure of the N,N'-dibutylated diazadibenzoperylenium dication 6, which revealed a 25degrees twist of the central six-membered ring leading to an atropisomeric pi-conjugated backbone. The chromophoric systems of 5 and 6 were characterized by optical absorption and fluorescence spectroscopy, which revealed an intense fluorescence with a quantum yield of 75% for 5 and 50% for 6. Cyclic voltammetry showed reversible oxidation and reduction waves for 6, whereas the oxidation of 5 afforded the irreversible deposition of a conductive film on the electrode surface. Finally, the potential use of ligands 5 in supramolecular chemistry has been evaluated by complexation experiments with carboxylic acids and zinc tetraphenylporphyrin (ZnTPP).