5,6,12,13-Tetraphenoxy-2,9-diazadibenzo[cd,lm]perylene | 272445-61-1

• 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-2,9-diazadibenzo[cd,lm]perylene
• 英文别名: 11,14,22,26-Tetraphenoxy-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1,3,5,7,9,11,13,15,17,19,21,23,25-tridecaene
• CAS: 272445-61-1
• 化学式: C₄₈H₂₈N₂O₄
• 分子量: 696.761
• InChiKey: MFQBMSHCQFGIOW-UHFFFAOYSA-N

物化性质

• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  54
• 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：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-bis(trifluoromethanesulfonate) bis(triphenylphosphine)palladium trihydrate 、 5,6,12,13-Tetraphenoxy-2,9-diazadibenzo[cd,lm]perylene 以 氘代氯仿 为溶剂， 生成
  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：

  N,N'-dibenzyl-1,6,7,12-tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisimide 在 10% palladium on active carbon lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 、 二苯醚 为溶剂， 反应 12.0h， 生成 5,6,12,13-Tetraphenoxy-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

文献信息

• A Triangle−Square Equilibrium of Metallosupramolecular Assemblies Based on Pd(II) and Pt(II) Corners and Diazadibenzoperylene Bridging Ligands
  作者：Armin Sautter、Dietmar G. Schmid、Günther Jung、Frank Würthner

  DOI：10.1021/ja004360y

  日期：2001.6.1

  which resulted in complex dynamic equilibria between molecular triangles 3a-d and molecular squares 4a-d in solution. Characterization of the equilibria and assignment of the metallacycles was accomplished by (1)H and (31)P[(1)H] NMR spectroscopy in combination with electrospray ionization Fourier transform ion cyclotron mass spectrometry (ESI-FTICR-MS). It was found that the equilibria depend on several

  四芳氧基取代的二氮杂二苯并苝桥连配体 1a、b 用于与 Pd(II) 和 Pt(II) 三氟甲磺酸酯 2a、b 的过渡金属定向自组装，这导致分子三角形 3a-d 和分子正方形 4a 之间复杂的动态平衡-d 在解决方案中。通过 (1) H 和 (31) P [(1) H] NMR 光谱结合电喷雾电离傅立叶变换离子回旋质谱 (ESI-FTICR-MS) 来完成金属环的平衡表征和分配。发现平衡取决于几个因素，例如金属离子（Pd(2+) 或 Pt(2+)）、溶剂和二氮杂二苯并苝配体 1a、b 的苯氧基取代基的空间需求。在 1b 中引入庞大的叔丁基使平衡在分子正方形的方向上显着移动。三角形和方形结构的分子动力学模拟揭示了磷烷和二氮杂二苯并苝配体的临界空间效应和受限的构象灵活性，这有助于解释在变温 NMR 研究中观察到的独特动态行为。浓度相关的 UV/vis 和荧光光谱揭示了组件的有限稳定性，并证实了
• 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).