1,4-diethynyl-9,10-dihydro-9,10- [1,2]-benzenoanthracene | 378233-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-diethynyl-9,10-dihydro-9,10- [1,2]-benzenoanthracene
• 英文别名: 3,6-Diethynylpentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene；3,6-diethynylpentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
• CAS: 378233-38-6
• 化学式: C₂₄H₁₄
• 分子量: 302.375
• InChiKey: KAYLISHHFBNYTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,4-bis(nonafluorobutylsulfonoxy)-9,10-dihydro-9,10-[1',2']benzenoanthracene 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 氢氧化钾 、 copper(l) iodide 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 44.5h， 生成 1,4-diethynyl-9,10-dihydro-9,10- [1,2]-benzenoanthracene
  参考文献：
  名称：

  Conjugated Polymers Containing 2,3-Dialkoxybenzene and Iptycene Building Blocks

  摘要：

  [GRAPHICS]Now poly(phenylene ethynylene)s (PPEs) and poly(phenylene vinylene)s (PPVs) that are highly emissive in solution and thin films were prepared utilizing palladium-catalyzed cross-coupling between new 1,4-dilodo-2,3-dialkoxybenzene- and iptycene-containing monomers. The absorption and emission spectra of the resulting polymers consistently showed a significant blue shift relative to the corresponding polymer analogues containing 2,5-dialkoxyphenylenes.

  DOI：

  10.1021/ol0164886

文献信息

• Synthesis and physical properties of triptycene-based oligo(p-phenyleneethynylene)s
  作者：Fei Zeng、Lin-Li Tang、Xiao-Ming Chen、Man-Hua Ding

  DOI：10.1016/j.tet.2018.10.011

  日期：2018.11

  A series of symmetrical and unsymmetrical triptycene-based oligo(op-phenyleneethynylene)s were synthesized by deprotection of the acetone protected terminal alkynes, followed by Sonogashira coupling reactions. The photophysical properties of triptycene-based OPEs both in solution and solid state have been investigated by UV–Vis and fluorescence spectroscopy. Interestingly, the obtained compounds show

  通过脱保护丙酮保护的末端炔烃，然后进行Sonogashira偶联反应，合成了一系列对称和不对称的基于三茂铁的低聚（对亚苯基乙炔基）。通过紫外线-可见光和荧光光谱研究了基于三萜烯的OPEs在溶液和固态下的光物理性质。有趣的是，所获得的化合物在固态下显示出强荧光且部分具有较高的量子产率，这表明三并茂部分不仅防止了分子间聚集，而且在固态下增强了OPEs骨架的共面性。
• Platinum Acetylide Complexes Containing Iptycene as Cores: A New Family of Unexpected Efficient Organometallic Gelators
  作者：Jing Zhang、Xing-Dong Xu、Li-Jun Chen、Qi Luo、Nai-Wei Wu、De-Xian Wang、Xiao-Li Zhao、Hai-Bo Yang

  DOI：10.1021/om2002987

  日期：2011.8.8

  and 13C) and mass spectroscopy and elemental analysis. Unexpectedly, all compounds presented good gel formation properties in some common organic solvents. The morphology of the xerogels was investigated by scanning electron microscopy (SEM). An investigation using electronic absorption and emission spectra was carried out to study the spectroscopic properties of all organometallic complexes in both

  已成功合成了新的含乙炔并以3,4,5-三（烷氧基）苯基取代基封端的茂金属构建基的乙炔铂衍生物新家族。新设计的配合物的结构通过多核NMR（1 H，31 P和13 C）以及质谱和元素分析进行表征。出乎意料的是，所有化合物在某些常见的有机溶剂中均表现出良好的凝胶形成性能。通过扫描电子显微镜（SEM）研究干凝胶的形态。进行了使用电子吸收和发射光谱的研究，以研究溶液和凝胶状态下所有有机金属配合物的光谱性质。
• Synthesis of triptycene-derived covalent organic polymer networks and their subsequent in-situ functionalization with 1,2-dicarbonyl substituents
  作者：Noorullah Baig、Suchetha Shetty、Saleh Al-Mousawi、Fakhreia Al-Sagheer、Bassam Alameddine

  DOI：10.1016/j.reactfunctpolym.2019.04.007

  日期：2019.6

  Three-dimensional polymer derivatives TP1-4 containing triptycene comonomers were synthesized from 1,4-diethynyl triptycene 1 with various di-, tri-, and tetra-brominated aromatic building blocks 3a-d through the mild Sonogashira cross-coupling reaction conditions. The abovementioned alkyne-containing copolymers were subsequently oxidized into their respective 1,2-diketone derivatives, OTP1-4, under mild reaction conditions. The UV-Vis and emission studies of copolymers TP1-4 and their oxidized homologues OTP1-4 confirmed the major influence of the aromatic substituent on the copolymer conjugation. Thermogravimetric analysis of copolymers TP1-4 revealed relatively high 10% weight loss temperature values (T-d) reaching up to 490 degrees C. On the other hand, the 1,2-diketone containing target polymers OTP1-4 showed lower 10% weight loss temperature values T-d, with a maximum of 431 degrees C.
• Conjugated Polymers Containing 2,3-Dialkoxybenzene and Iptycene Building Blocks
  作者：Zhengguo Zhu、Timothy M. Swager

  DOI：10.1021/ol0164886

  日期：2001.11.1

  [GRAPHICS]Now poly(phenylene ethynylene)s (PPEs) and poly(phenylene vinylene)s (PPVs) that are highly emissive in solution and thin films were prepared utilizing palladium-catalyzed cross-coupling between new 1,4-dilodo-2,3-dialkoxybenzene- and iptycene-containing monomers. The absorption and emission spectra of the resulting polymers consistently showed a significant blue shift relative to the corresponding polymer analogues containing 2,5-dialkoxyphenylenes.
• 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.