2,7-bis[(4-methoxyphenyl)ethynyl]-9H-fluoren-9-one | 293757-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-bis[(4-methoxyphenyl)ethynyl]-9H-fluoren-9-one
• 英文别名: 2,7-bis-(4-methoxyphenylethynyl)fluoren-9-one；2,7-Bis[2-(4-methoxyphenyl)ethynyl]fluoren-9-one；2,7-bis[2-(4-methoxyphenyl)ethynyl]fluoren-9-one
• CAS: 293757-13-8
• 化学式: C₃₁H₂₀O₃
• 分子量: 440.498
• InChiKey: KHXROHDFSSACRE-UHFFFAOYSA-N

物化性质

• 沸点：
  678.6±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,7-bis[(4-methoxyphenyl)ethynyl]-9H-fluoren-9-one 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到2,7-bis[2-(4-methoxyphenyl)ethyl]-9H-fluoren-9-one
  参考文献：
  名称：

  摘要：

  As part of our studies on the tetramerization of quinodimethane 1 to the macrocyclic compound 2, the influence of substituents on this reaction was investigated. It was found that a large range of substituents such as 2-phenylethyl, 2-(4-methoxyphenyl)ethyl, 2-(4-fluorephenyl)ethyl, 2-[4-(tert-butyl)phenyl]ethyl, and 2-[4-(2-phenylethyl)phenyl]ethyl, attached at positions 2 and 7 of 9H-fluorene, do net prevent the tetramerization. The key step in the formation of the macrocylic compounds 13a-e is the debromination of 12a-e with mercury to the corresponding quinodimethanes which undergo a self-assembly forming 13a-e in high yields To study the conjugative influence of substituents on tetramerization, the effect of the hex-1-ynyl groups at positions 3 and 6 of the 9H-fluorene rings was investigated. In this case, the corresponding macrocycle 17 was generated by the reaction of diol 16a with SnCl2. Although the expected tetramerization to 17 occurred, the yield was lower than in the case of 13a-e, due to the sensitivity of the product.

  DOI：

  10.1002/1522-2675(20000607)83:6<1224::aid-hlca1224>3.0.co;2-n
• 作为产物：
  描述：

  9-芴酮 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 硫酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2,7-bis[(4-methoxyphenyl)ethynyl]-9H-fluoren-9-one
  参考文献：
  名称：

  芴酮基分子的合成及双光子吸收光谱

  摘要：

  摘要 通过飞秒波长可调 Z 扫描和量子化学计算研究了五种对称芴酮基分子的双光子吸收 (2PA)。这些分子对于大于 500 nm 的波长是透明的，在蓝色区域观察到两个主要的单光子吸收带；一种较弱，以 450 nm 为中心，另一种在约 360 nm 处较强。我们观察到位于 720 nm 附近的强 2PA 波段，最大 2PA 横截面在 100 到 230 GM 之间。使用响应函数形式的量子化学计算在密度函数理论水平上进行，以支持对实验非线性光谱的解释。

  DOI：

  10.1016/j.cplett.2016.08.068

文献信息

• ——
  作者：Junes Ipaktschi、Rahman Hosseinzadeh、Peter Schlaf、Thomas Eckert

  DOI：10.1002/1522-2675(20000607)83:6<1224::aid-hlca1224>3.0.co;2-n

  日期：2000.6.7

  As part of our studies on the tetramerization of quinodimethane 1 to the macrocyclic compound 2, the influence of substituents on this reaction was investigated. It was found that a large range of substituents such as 2-phenylethyl, 2-(4-methoxyphenyl)ethyl, 2-(4-fluorephenyl)ethyl, 2-[4-(tert-butyl)phenyl]ethyl, and 2-[4-(2-phenylethyl)phenyl]ethyl, attached at positions 2 and 7 of 9H-fluorene, do net prevent the tetramerization. The key step in the formation of the macrocylic compounds 13a-e is the debromination of 12a-e with mercury to the corresponding quinodimethanes which undergo a self-assembly forming 13a-e in high yields To study the conjugative influence of substituents on tetramerization, the effect of the hex-1-ynyl groups at positions 3 and 6 of the 9H-fluorene rings was investigated. In this case, the corresponding macrocycle 17 was generated by the reaction of diol 16a with SnCl2. Although the expected tetramerization to 17 occurred, the yield was lower than in the case of 13a-e, due to the sensitivity of the product.
• Synthesis and two-photon absorption spectrum of fluorenone-based molecules
  作者：J. Dipold、R.J.M.B. Batista、R.D. Fonseca、D.L. Silva、G.L.C. Moura、J.V. dos Anjos、A.M. Simas、L. De Boni、C.R. Mendonca

  DOI：10.1016/j.cplett.2016.08.068

  日期：2016.9

  Abstract The two-photon absorption (2PA) of five symmetrical fluorenone-based molecules is studied by femtosecond wavelength-tunable Z-scan, as well as quantum-chemical calculations. The molecules are transparent for wavelengths greater than 500 nm and two main one-photon absorption bands are observed in the blue region; one weak, centered at 450 nm, and a stronger one at approximately 360 nm. We observed

  摘要 通过飞秒波长可调 Z 扫描和量子化学计算研究了五种对称芴酮基分子的双光子吸收 (2PA)。这些分子对于大于 500 nm 的波长是透明的，在蓝色区域观察到两个主要的单光子吸收带；一种较弱，以 450 nm 为中心，另一种在约 360 nm 处较强。我们观察到位于 720 nm 附近的强 2PA 波段，最大 2PA 横截面在 100 到 230 GM 之间。使用响应函数形式的量子化学计算在密度函数理论水平上进行，以支持对实验非线性光谱的解释。