hexakis(p-methoxyphenylethynyl)benzene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: hexakis(p-methoxyphenylethynyl)benzene
• 英文别名: hexakis(4-methoxyphenylethynyl)benzene；1,2,3,4,5,6-Hexakis[2-(4-methoxyphenyl)ethynyl]benzene；1,2,3,4,5,6-hexakis[2-(4-methoxyphenyl)ethynyl]benzene
• 化学式: C₆₀H₄₂O₆
• 分子量: 858.99
• InChiKey: OIWOLXFTMOVPQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  66
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  六溴苯 、 4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 反应 112.0h， 以68%的产率得到hexakis(p-methoxyphenylethynyl)benzene
  参考文献：
  名称：

  Synthesis and Self-Association, Absorption, and Fluorescence Properties of Differentially Functionalized Hexakis(p-substituted-phenylethynyl)benzenes

  摘要：

  The dual Sonogashira coupling reactions of 1,3,5-tribromo-2,4,6-triiodobenzene with p-X-phenylacetylene followed by another p-Y-phenylacetylene (X, Y = OsiMe(2)Bu-t or CO2Et) produced a series of differentially functionalized hexakis(p-substituted-phenylethynyl)benzenes with D-3h symmetry (3h: 1,3,5-X-2,4,6-Y) and C-2nu symmetry (3g,i: 1,2,3,5-X-4,6-Y; 3f,j: 1-X-2,3,4,5,6-Y). In a similar manner, 1,3,5-tris(p-X-phenylethynyl)-2,4,6-tris(p-Y-phenylethynyl)benzenes and 1,2,3,5-tetrakis(p-X-phenylethynyl)-4,6-bis(p-Y-phenylethynyl)benzenes (31: X = OSiMe2Bu-t, Y = NO2; 3m,n: X = N(n-octyl)(2), Y = NO2; 3o,p: X = N(n-octyl)(2), Y = CH(OCH2CH2O); 3q,r: X = N(n-octyl)(2), Y = CHO; 3s,t: X = N(n-octyl)(2), Y = CH=C(CN)(2)) were prepared. Compounds 3 with electron-withdrawing groups self-aggregated by a pi-pi stacking interaction and solvophobic effect. In the absorption and fluorescence spectra of 3, lambda(max)(abs) and lambda(max)(em) showed red shifts as the donor-acceptor dipole at the end functional groups of the para position was increased. In the absorption spectra, lambda(max)(abs) showed red shifts upon increasing the number of combination of electron-donating and -withdrawing groups on the diagonal line in a molecule, whereas lambda(max)(em) in the fluorescence spectra exhibited red shifts upon decreasing the molecular symmetry.

  DOI：

  10.1021/jo049948s

文献信息

• Multiple Sonogashira Reactions of Polychlorinated Molecules. Synthesis and Photophysical Properties of the First Pentaalkynylpyridines
  作者：Peter Ehlers、Antje Neubauer、Stefan Lochbrunner、Alexander Villinger、Peter Langer

  DOI：10.1021/ol2000183

  日期：2011.4.1

  Hitherto unknown pentaalkynylpyridines have been prepared in high yields by Sonogashira cross-coupling reactions of pentachloropyridine. Their photophysical properties were studied and compared to those of penta- and hexaalkynylbenzenes which were efficiently prepared by the first Sonogashira reactions of pentachlorobenzene and hexachlorobenzene. The pentaalkynylpyridines show promising fluorescence properties because of their high quantum yields.
• Synthesis and Self-Association, Absorption, and Fluorescence Properties of Differentially Functionalized Hexakis(<i>p</i>-substituted-phenylethynyl)benzenes
  作者：Kenji Kobayashi、Norifumi Kobayashi

  DOI：10.1021/jo049948s

  日期：2004.4.1

  The dual Sonogashira coupling reactions of 1,3,5-tribromo-2,4,6-triiodobenzene with p-X-phenylacetylene followed by another p-Y-phenylacetylene (X, Y = OsiMe(2)Bu-t or CO2Et) produced a series of differentially functionalized hexakis(p-substituted-phenylethynyl)benzenes with D-3h symmetry (3h: 1,3,5-X-2,4,6-Y) and C-2nu symmetry (3g,i: 1,2,3,5-X-4,6-Y; 3f,j: 1-X-2,3,4,5,6-Y). In a similar manner, 1,3,5-tris(p-X-phenylethynyl)-2,4,6-tris(p-Y-phenylethynyl)benzenes and 1,2,3,5-tetrakis(p-X-phenylethynyl)-4,6-bis(p-Y-phenylethynyl)benzenes (31: X = OSiMe2Bu-t, Y = NO2; 3m,n: X = N(n-octyl)(2), Y = NO2; 3o,p: X = N(n-octyl)(2), Y = CH(OCH2CH2O); 3q,r: X = N(n-octyl)(2), Y = CHO; 3s,t: X = N(n-octyl)(2), Y = CH=C(CN)(2)) were prepared. Compounds 3 with electron-withdrawing groups self-aggregated by a pi-pi stacking interaction and solvophobic effect. In the absorption and fluorescence spectra of 3, lambda(max)(abs) and lambda(max)(em) showed red shifts as the donor-acceptor dipole at the end functional groups of the para position was increased. In the absorption spectra, lambda(max)(abs) showed red shifts upon increasing the number of combination of electron-donating and -withdrawing groups on the diagonal line in a molecule, whereas lambda(max)(em) in the fluorescence spectra exhibited red shifts upon decreasing the molecular symmetry.