1,4-bis(pyridin-4-ylethynyl)-9,10-dihydro-9,10-[1',2]benzeneanthracene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-bis(pyridin-4-ylethynyl)-9,10-dihydro-9,10-[1',2]benzeneanthracene
• 英文别名: 4-[2-[6-(2-Pyridin-4-ylethynyl)-3-pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaenyl]ethynyl]pyridine；4-[2-[6-(2-pyridin-4-ylethynyl)-3-pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaenyl]ethynyl]pyridine
• 化学式: C₃₄H₂₀N₂
• 分子量: 456.546
• InChiKey: ZNHJVZSQNUOQGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [Ru₂(μ-η⁴-C₁₈H₈O₄)(η⁶-p-cymene)₂][O₃SCF₃]₂ 、 1,4-bis(pyridin-4-ylethynyl)-9,10-dihydro-9,10-[1',2]benzeneanthracene 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以94%的产率得到
  参考文献：
  名称：

  Self-assembly of new arene-ruthenium rectangles containing triptycene building block and their application in fluorescent detection of nitro aromatics

  摘要：

  A suite of two new tetraruthenium metallarectangles 5 and 6 have been obtained from [2+2] self-assemblies between dipyridylethynyltriptycene 2 and one of the two dinuclear arene ruthenium clips, [Ru-2 (mu-eta(4)-OO boolean AND OO) (eta(6)-p-cymene)(2)][OTf](2); (OO boolean AND OO = oxalate 3; 6,11-dihydroxy-5,12-naphthacenedionato (dotq) 4; OTf = triflate). These molecular rectangles are fully characterized by H-1 NMR spectroscopy, electrospray mass spectrometry. A single crystal of 6 was suitable for X-ray diffraction structural characterization. These new metallarectangles showed fluorescence behavior in solution, have been examined for emission quenching effects with various aromatic compounds, and show high quenching selectivity and sensitivity towards nitroaromatics, particularly picric acid and 1,3,5-trinitrobenzene. Excited-state charge transfer from the rectangles to nitro aromatic substrates can be used to develop selective fluorescent sensors for nitro aromatics. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.08.037
• 作为产物：
  描述：

  4-碘吡啶 、 1,4-diethynyl-9,10-dihydro-9,10- [1,2]-benzenoanthracene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以85%的产率得到1,4-bis(pyridin-4-ylethynyl)-9,10-dihydro-9,10-[1',2]benzeneanthracene
  参考文献：
  名称：

  Self-assembly of new arene-ruthenium rectangles containing triptycene building block and their application in fluorescent detection of nitro aromatics

  摘要：

  A suite of two new tetraruthenium metallarectangles 5 and 6 have been obtained from [2+2] self-assemblies between dipyridylethynyltriptycene 2 and one of the two dinuclear arene ruthenium clips, [Ru-2 (mu-eta(4)-OO boolean AND OO) (eta(6)-p-cymene)(2)][OTf](2); (OO boolean AND OO = oxalate 3; 6,11-dihydroxy-5,12-naphthacenedionato (dotq) 4; OTf = triflate). These molecular rectangles are fully characterized by H-1 NMR spectroscopy, electrospray mass spectrometry. A single crystal of 6 was suitable for X-ray diffraction structural characterization. These new metallarectangles showed fluorescence behavior in solution, have been examined for emission quenching effects with various aromatic compounds, and show high quenching selectivity and sensitivity towards nitroaromatics, particularly picric acid and 1,3,5-trinitrobenzene. Excited-state charge transfer from the rectangles to nitro aromatic substrates can be used to develop selective fluorescent sensors for nitro aromatics. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.08.037

文献信息

• Self-assembly of new arene-ruthenium rectangles containing triptycene building block and their application in fluorescent detection of nitro aromatics
  作者：Abhishek Dubey、Anurag Mishra、Jin Wook Min、Min Hyung Lee、Hyunuk Kim、Peter J. Stang、Ki-Whan Chi

  DOI：10.1016/j.ica.2014.08.037

  日期：2014.11

  A suite of two new tetraruthenium metallarectangles 5 and 6 have been obtained from [2+2] self-assemblies between dipyridylethynyltriptycene 2 and one of the two dinuclear arene ruthenium clips, [Ru-2 (mu-eta(4)-OO boolean AND OO) (eta(6)-p-cymene)(2)][OTf](2); (OO boolean AND OO = oxalate 3; 6,11-dihydroxy-5,12-naphthacenedionato (dotq) 4; OTf = triflate). These molecular rectangles are fully characterized by H-1 NMR spectroscopy, electrospray mass spectrometry. A single crystal of 6 was suitable for X-ray diffraction structural characterization. These new metallarectangles showed fluorescence behavior in solution, have been examined for emission quenching effects with various aromatic compounds, and show high quenching selectivity and sensitivity towards nitroaromatics, particularly picric acid and 1,3,5-trinitrobenzene. Excited-state charge transfer from the rectangles to nitro aromatic substrates can be used to develop selective fluorescent sensors for nitro aromatics. (C) 2014 Elsevier B.V. All rights reserved.