5,5,7,7-Tetrakis(4-fluorophenyl)-6-oxatetracyclo[6.5.2.04,15.011,14]pentadeca-1(14),2,4(15),8,10-pentaene | 1165940-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,5,7,7-Tetrakis(4-fluorophenyl)-6-oxatetracyclo[6.5.2.04,15.011,14]pentadeca-1(14),2,4(15),8,10-pentaene
• 英文别名: 5,5,7,7-tetrakis(4-fluorophenyl)-6-oxatetracyclo[6.5.2.04,15.011,14]pentadeca-1(14),2,4(15),8,10-pentaene
• CAS: 1165940-01-1
• 化学式: C₃₈H₂₄F₄O
• 分子量: 572.602
• InChiKey: SWWJEEIDRYUYGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  43
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5,7,7-Tetrakis(4-fluorophenyl)-6-oxatetracyclo[6.5.2.04,15.011,14]pentadeca-1(14),2,4(15),8,10-pentaene 在 trimethylsilyl perchlorate 、 锌 作用下， 以 六氟异丙醇 、 乙腈 为溶剂， 生成 1,1,2,2-tetrakis(4-fluorophenyl)pyracene
  参考文献：
  名称：

  Negligible diradical character for the ultralong C–C bond in 1,1,2,2-tetraarylpyracene derivatives at room temperature

  摘要：

  There is evidence that the crystalline-state thermochromic behavior of dispiropyracene acr-1 with an ultralong C-C bond [1.791(3) angstrom at 413 K, 1.771(3) angstrom at 93K] might be due to thermal generation of a bond-dissociated triplet diradical. The C-1-C-2 bond lengths (d) in the newly prepared 1,1,2,2-tetraarylpyracenes 1a-e [1.717(4)-1.761(4) angstrom at 113/123/153 K] are also much larger than the standard value for C(sp(3))-C(sp(3)) (1.54 angstrom). The fact that there is no correlation between d and the radical-stabilizing parameter (sigma(center dot)) provides evidence that there is no contribution from a crystallographic artifact caused by contamination of the diradical in the crystal of 1 at room temperature or below. Further indication for the covalent nature of the ultralong C-C bond in tetraphenylpyracene 1c was attained by Raman spectroscopy, showing the far Fed-shifted C-1-C-2 Stretching vibration (638 cm(-1)) and by the theoretical prediction of very large vertical singlet-triplet energy gap (58.3 kcal mol(-1) at the UB3LYP/6-31G* level). However, at elevated temperatures bond dissociation might occur forming a triplet diradical. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.202
• 作为产物：
  描述：

  5,6-二溴苊 、 4,4'-二氟二苯甲酮 在 正丁基锂 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 5,5,7,7-Tetrakis(4-fluorophenyl)-6-oxatetracyclo[6.5.2.04,15.011,14]pentadeca-1(14),2,4(15),8,10-pentaene
  参考文献：
  名称：

  Negligible diradical character for the ultralong C–C bond in 1,1,2,2-tetraarylpyracene derivatives at room temperature

  摘要：

  There is evidence that the crystalline-state thermochromic behavior of dispiropyracene acr-1 with an ultralong C-C bond [1.791(3) angstrom at 413 K, 1.771(3) angstrom at 93K] might be due to thermal generation of a bond-dissociated triplet diradical. The C-1-C-2 bond lengths (d) in the newly prepared 1,1,2,2-tetraarylpyracenes 1a-e [1.717(4)-1.761(4) angstrom at 113/123/153 K] are also much larger than the standard value for C(sp(3))-C(sp(3)) (1.54 angstrom). The fact that there is no correlation between d and the radical-stabilizing parameter (sigma(center dot)) provides evidence that there is no contribution from a crystallographic artifact caused by contamination of the diradical in the crystal of 1 at room temperature or below. Further indication for the covalent nature of the ultralong C-C bond in tetraphenylpyracene 1c was attained by Raman spectroscopy, showing the far Fed-shifted C-1-C-2 Stretching vibration (638 cm(-1)) and by the theoretical prediction of very large vertical singlet-triplet energy gap (58.3 kcal mol(-1) at the UB3LYP/6-31G* level). However, at elevated temperatures bond dissociation might occur forming a triplet diradical. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.202

文献信息

• Negligible diradical character for the ultralong C–C bond in 1,1,2,2-tetraarylpyracene derivatives at room temperature
  作者：Takashi Takeda、Hidetoshi Kawai、Rainer Herges、Eva Mucke、Yoshitaka Sawai、Kei Murakoshi、Kenshu Fujiwara、Takanori Suzuki

  DOI：10.1016/j.tetlet.2009.03.202

  日期：2009.7

  There is evidence that the crystalline-state thermochromic behavior of dispiropyracene acr-1 with an ultralong C-C bond [1.791(3) angstrom at 413 K, 1.771(3) angstrom at 93K] might be due to thermal generation of a bond-dissociated triplet diradical. The C-1-C-2 bond lengths (d) in the newly prepared 1,1,2,2-tetraarylpyracenes 1a-e [1.717(4)-1.761(4) angstrom at 113/123/153 K] are also much larger than the standard value for C(sp(3))-C(sp(3)) (1.54 angstrom). The fact that there is no correlation between d and the radical-stabilizing parameter (sigma(center dot)) provides evidence that there is no contribution from a crystallographic artifact caused by contamination of the diradical in the crystal of 1 at room temperature or below. Further indication for the covalent nature of the ultralong C-C bond in tetraphenylpyracene 1c was attained by Raman spectroscopy, showing the far Fed-shifted C-1-C-2 Stretching vibration (638 cm(-1)) and by the theoretical prediction of very large vertical singlet-triplet energy gap (58.3 kcal mol(-1) at the UB3LYP/6-31G* level). However, at elevated temperatures bond dissociation might occur forming a triplet diradical. (C) 2009 Elsevier Ltd. All rights reserved.