1,3,5-tris[p-(tert-butyldimethylsilyloxy)phenylethynyl]-2,4,6-tris[p-(ethoxycarbonyl)phenylethynyl]benzene | 684216-84-0

• 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: 1,3,5-tris[p-(tert-butyldimethylsilyloxy)phenylethynyl]-2,4,6-tris[p-(ethoxycarbonyl)phenylethynyl]benzene
• 英文别名: Ethyl 4-[2-[2,4,6-tris[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]ethynyl]-3,5-bis[2-(4-ethoxycarbonylphenyl)ethynyl]phenyl]ethynyl]benzoate；ethyl 4-[2-[2,4,6-tris[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]ethynyl]-3,5-bis[2-(4-ethoxycarbonylphenyl)ethynyl]phenyl]ethynyl]benzoate
• CAS: 684216-84-0
• 化学式: C₈₁H₈₄O₉Si₃
• 分子量: 1285.81
• InChiKey: OGNYWNODLBZPJM-UHFFFAOYSA-N

物化性质

• 沸点：
  1077.5±65.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.77
• 重原子数：
  93
• 可旋转键数：
  30
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,5-tris[p-(tert-butyldimethylsilyloxy)phenylethynyl]-2,4,6-tris[p-(ethoxycarbonyl)phenylethynyl]benzene 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 以99%的产率得到1,3,5-tris(p-carboxyphenylethynyl)-2,4,6-tris(p-hydroxyphenylethynyl)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
• 作为产物：
  描述：

  1,3,5-三溴-2,4,6-三碘苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 反应 89.0h， 生成 1,3,5-tris[p-(tert-butyldimethylsilyloxy)phenylethynyl]-2,4,6-tris[p-(ethoxycarbonyl)phenylethynyl]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

• 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.