4,4`-bis(pentafluorophenyl) perfluoro biphenyl | 3008-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4`-bis(pentafluorophenyl) perfluoro biphenyl
• 英文别名: perfluro-(1,1':4',1'':4'',1'''-quaterphenyl)；perfluoro-p-quaterphenyl；Perfluor-(4',4'')-quaterphenyl；Perfluor-p-quaterphenyl；1,2,3,4,5-pentafluoro-6-[2,3,5,6-tetrafluoro-4-[2,3,5,6-tetrafluoro-4-(2,3,4,5,6-pentafluorophenyl)phenyl]phenyl]benzene
• CAS: 3008-32-0
• 化学式: C₂₄F₁₈
• 分子量: 630.235
• InChiKey: VYDAGSVBURVFDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  十氟联苯 、 三甲基五氟苯基硅烷 在 potassium hydrogen difluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以73%的产率得到perfluoro-(1,1':4',1'':4'',1''':4''',1''''-quinquephenyl)
  参考文献：
  名称：

  Formation of perfluorinated polyphenylenes by multiple pentafluorophenylation using C6F5Si(CH3)3

  摘要：

  Pentafluorophenylation of perfluoroarenes with C6F5Si(CH3)(3) was investigated by using NMR and MALDI-TOF-MS techniques. Successive multiple pentafluorophenylation easily occurred not only on the para-position but also on the ortho-positions to provide perfluorinated p-phenylene and m-phenylene compounds. The perfluoroarenes having electron-withdrawing substituents provided oligo- to poly-(phenylene)s depending on the added amounts of C6F5Si(CH3)(3), while the perfluoroarenes having electron-donor substituents gave H(C6F4)(n)F polymers produced from C6F5H, which was the decomposed product of C6F5Si(CH3)(3). (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.09.001

文献信息

• Photocatalysis of Perfluorinated Oligo(<i>p</i>-Phenylene)s
  作者：Katsuya Maruo、Yuji Wada、Shozo Yanagida

  DOI：10.1246/bcsj.65.3439

  日期：1992.12

  spectra, a decrease in their fluorescence quantum yields, an increase in their fluorescence lifetimes, and a positive shift of their oxidation potentials. The resulting perfluorinated oligo(p-phenylene)s (F-OPP-n, n = 3 and 4) shows photocatalytic activities for the photoreduction of water and for the photooxidation of benzene to phenol. Irradiation of an aqueous methanol solution of F-OPP-3 with triethylamine

  低聚（对亚苯基）（OPP-n）、联苯（OPP-2）全氟化成对四联苯（OPP-4），导致 OPP-n 的光谱和物理特性发生各种变化；它们的吸收光谱发生低色移，荧光量子产率降低，荧光寿命增加，氧化电位正移。所得全氟化低聚（对亚苯基）（F-OPP-n，n = 3 和 4）显示出光催化水的光还原和苯光氧化为苯酚的光催化活性。用三乙胺作为电子供体和贵金属胶体作为电子介体在 λ > 290 nm 处照射 F-OPP-3 的甲醇水溶液会导致 H2 析出，尽管通过 F-OPP-3−• 不可避免地发生光脱氟到可观的程度。
• Biradical with a polyfluorinated terphenylene backbone
  作者：P. A. Fedyushin、A. A. Serykh、A. S. Vinogradov、T. V. Mezhenkova、V. E. Platonov、D. I. Nasyrova、A. I. Samigullina、M. V. Fedin、I. A. Zayakin、E. V. Tretyakov

  DOI：10.1007/s11172-022-3577-0

  日期：2022.8

  A method was developed for the synthesis of perfluoro-1,1′:4′,1″-terphenyl by the reaction of chloroperfluorobenzene with zinc dust followed by the reaction of the resulting mixture of C6F5ZnCl and (C6F5)2Zn with decafluorobiphenyl in the presence of KF. The reaction of perfluoro-1,1′:4′,1″-terphenyl with tert-butylamine in an autoclave gives the aminodefluorination product, 4,4″-bis(tert-butylamino)perfluoro-1,1′:4′,1″-terphenyl, and the oxidation of the latter with m-chloroperbenzoic acid affords a new stable nitroxide biradical 4,4″-bis(N-tert-butyl-N-oxylamino)perfluoro-1,1′:4′,1″-terphenyl in quantitative yield. The molecular and crystal structures of the diamine and the biradical were established by X-ray diffraction. According to the X-ray diffraction data, the planes of the paramagnetic moieties and the aromatic rings are significantly rotated with respect to each other, resulting in weak intramolecular exchange interactions between the paramagnetic centers.

  通过氯全氟苯与锌粉反应，然后通过所得的C6F5ZnCl和（C6F5）2Zn混合物与十氟联苯在KF存在下的反应，开发了一种全氟-1,1′:4′,1″-三联苯的合成方法。全氟-1,1′:4′,1″-三联苯与叔丁胺在高压釜中的反应可得到氨基脱氟产物4,4″-双（叔丁基氨基）全氟-1,1′:4′,1″-三联苯，后者与间氯过氧苯甲酸的氧化反应可定量生成一种新的稳定硝基全氟-1,1′:4′,1″-三联苯4,4″-双（N-叔丁基-N-氧基氨基）全氟-1,1′:4′,1″-三联苯。通过X射线衍射确定了二胺和双自由基的分子和晶体结构。根据X射线衍射数据，顺磁部分和芳香环的平面相对于彼此明显旋转，导致顺磁中心之间存在微弱的分子内交换相互作用。
• Shtark, A. A.; Chuikova, T. V.; Shteingarts, V. D., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 5, p. 960 - 967
  作者：Shtark, A. A.、Chuikova, T. V.、Shteingarts, V. D.

  DOI：——

  日期：——
• SHTARK, A. A.;CHUJKOVA, T. V.;SHTEJNGARTS, V. D., ZH. ORGAN. XIMII, 1984, 20, N 5, 1055-1063
  作者：SHTARK, A. A.、CHUJKOVA, T. V.、SHTEJNGARTS, V. D.

  DOI：——

  日期：——
• Formation of perfluorinated polyphenylenes by multiple pentafluorophenylation using C6F5Si(CH3)3
  作者：Masakazu Nishida、Yoshio Hayakawa、Taizo Ono

  DOI：10.1016/j.jfluchem.2010.09.001

  日期：2010.12

  Pentafluorophenylation of perfluoroarenes with C6F5Si(CH3)(3) was investigated by using NMR and MALDI-TOF-MS techniques. Successive multiple pentafluorophenylation easily occurred not only on the para-position but also on the ortho-positions to provide perfluorinated p-phenylene and m-phenylene compounds. The perfluoroarenes having electron-withdrawing substituents provided oligo- to poly-(phenylene)s depending on the added amounts of C6F5Si(CH3)(3), while the perfluoroarenes having electron-donor substituents gave H(C6F4)(n)F polymers produced from C6F5H, which was the decomposed product of C6F5Si(CH3)(3). (C) 2010 Elsevier B.V. All rights reserved.