5,6,12,13-tetraphenoxy-1,3,8,10-tetrahydro-2,9-dibutyl-2,9-diazadibenzo[cd,lm]perylene | 272445-59-7

• 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: 5,6,12,13-tetraphenoxy-1,3,8,10-tetrahydro-2,9-dibutyl-2,9-diazadibenzo[cd,lm]perylene
• 英文别名: 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；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
• CAS: 272445-59-7
• 化学式: C₅₆H₅₀N₂O₄
• 分子量: 815.024
• InChiKey: PWQUBAHNISXCEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  62
• 可旋转键数：
  14
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6,12,13-tetraphenoxy-1,3,8,10-tetrahydro-2,9-dibutyl-2,9-diazadibenzo[cd,lm]perylene 在 mercury(II) diacetate 、 tetrafluoroboric acid 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 以51%的产率得到5,6,12,13-tetraphenoxy-2,9-dibutyl-2,9-diazadibenzo[cd,lm]perylenium bis(tetrafluoroborate)
  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 、 lithium aluminium tetrahydride 、 三氯化铝 、 potassium carbonate 、 丙酸 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 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：

  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

• 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).