trans,trans-1,4-bis(2-phenylethenyl)-2,3,5,6-tetrafluorobenzene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans,trans-1,4-bis(2-phenylethenyl)-2,3,5,6-tetrafluorobenzene
• 英文别名: ((1E,1'E)-(perfluoro-1,4-phenylene)bis(ethene-2,1-diyl))dibenzene；(1E,1'E)-2,2'-(perfluoro-1,4-phenylene)bis(ethene-2,1-diyl)dibenzene；1,2,4,5-tetrafluoro-3,6-bis[(E)-2-phenylethenyl]benzene
• 化学式: C₂₂H₁₄F₄
• 分子量: 354.347
• InChiKey: MFPMYIGGNXWVBS-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• 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：
  4

反应信息

• 作为产物：
  描述：

  2,3,5,6-四氟对二甲苯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 均三甲苯 、 苯 为溶剂， 反应 146.0h， 生成 trans,trans-1,4-bis(2-phenylethenyl)-2,3,5,6-tetrafluorobenzene
  参考文献：
  名称：

  通过合理的单体设计控制亚乙烯基连接的二维共轭聚合物的结晶度

  摘要：

  我们揭示了通过 Horner-Wadsworth-Emmons (HWE) 缩聚溶剂热合成 2D-聚(亚苯基喹喔啉亚乙烯基) (2D-PPQV) 和 2D-​​聚(亚苯基-亚乙烯基) (2D-PPV) 过程中结晶度的控制：使用氟化膦酸盐和刚性醛结构单元。

  DOI：

  10.1002/chem.202104502

文献信息

• Pd(OAc)₂ Catalyzed Olefination of Highly Electron-Deficient Perfluoroarenes
  作者：Xingang Zhang、Shilu Fan、Chun-Yang He、Xiaolong Wan、Qiao-Qiao Min、Jie Yang、Zhong-Xing Jiang

  DOI：10.1021/ja908434e

  日期：2010.4.7

  An efficient, Pd(OAc)(2) catalyzed method for direct olefination of highly electron-deficient perfluoroarenes was developed. The reaction scope includes a series of activated and nonactivated alkenes in moderate to high yields with moderate to high regio- and stereoselectivities.
• Phenyl−Perfluorophenyl Stacking Interactions:  Topochemical [2+2] Photodimerization and Photopolymerization of Olefinic Compounds
  作者：Geoffrey W. Coates、Alex R. Dunn、Lawrence M. Henling、Joseph W. Ziller、Emil B. Lobkovsky、Robert H. Grubbs

  DOI：10.1021/ja974072a

  日期：1998.4.1

  The face-to-face stacking interaction between phenyl and perfluorophenyl groups is emerging as a common noncovalent interaction. To explore the generality of this supramolecular synthon, the solid-state packing structure and reactivity of several monoolefins and diolefins substituted with phenyl and perfluorophenyl groups was investigated. Of the seven crystalline or cocrystalline materials investigated, six were found to undergo a photochemically induced [2+2] reaction in the solid state. By determining the stereochemistry of the photoproduct and/or X-ray structural analysis of the olefinic precursors, the stacked interaction between phenyl and perfluorophenyl groups in the photoactive crystals were revealed.
• Effect of Aromatic Ring Substitution on the Optical Properties, Emission Dynamics, and Solid-State Behavior of Fluorinated Oligophenylenevinylenes
  作者：Bernd Strehmel、Ananda M. Sarker、John H. Malpert、Veronika Strehmel、Holger Seifert、Douglas C. Neckers

  DOI：10.1021/ja983308n

  日期：1999.2.1

  Several substituted oligopbenylenevinylenes were synthesized using the Wittig-Horner-Emmons reaction to produce the trans isomers. Optical properties of these compounds were evaluated using absorption and steady-state fluorescence spectroscopy. Fluorescence quantum yields, Phi(f), decrease with increasing solvent polarity and approach unity in nonpolar solvents In the case of substituted trans,trans-1,4-bis[2-(2',5'-difluoro)-phenylethenyl]benzenes and trans,trans-1,4-bis[2-(2',5'-dialkoxy)phenylethenyl)-2,3,5,6-tetrafluorobenzenes. The compounds show a strong solvatochromic shift as a function of solvent polarity, yielding a slope of -13 300 cm(-1) according to the Lippert-Mataga equation and indicating the emission of an additional charge-transfer species. A two-state reaction model was confirmed for trans,trans-1,4-bis[2-(2',5'dialkoxy)phenylethenyl)-2,3,5,6-tetratfluorobenzene (6d) in different solvents by time-correlated single-photon counting using global analysis. A dependence of the kinetic data on solvent polarity was found (global fitted decay times in picoseconds for tau(1) and tau(2): 381/1281 in n-hexane; 101/1590 in toluene; 27/2974 in acetonitrile). Investigations of the solid state showed liquid crystalline behavior for 6d and for trans,trans-1,4-bis[2-(2',5'-difluoro)phenylethenyl] 2,5-diheptyloxybenzene (3b). This was confirmed by polarization microscopy and thermal analysis. Both the long alkoxy chains and fluorine substitution are responsible for the formation of mesophases. Photoluminescence studies of 3b and 6d in the solid state indicated an intense emission that was yellow for 3b.
• Control of Crystallinity of Vinylene‐Linked Two‐Dimensional Conjugated Polymers by Rational Monomer Design
  作者：Dominik L. Pastoetter、Yannan Liu、Matthew A. Addicoat、Silvia Paasch、Arezoo Dianat、David Bodesheim、Albrecht L. Waentig、Shunqi Xu、Mino Borrelli、Alexander Croy、Marcus Richter、Eike Brunner、Gianaurelio Cuniberti、Xinliang Feng

  DOI：10.1002/chem.202104502

  日期：2022.4.6

  We reveal the control of crystallinity during the solvothermal synthesis of 2D-poly(phenylenequinoxalinevinylene)s (2D-PPQVs) and 2D-poly(phenylene-vinylene)s (2D-PPVs) through the Horner-Wadsworth-Emmons (HWE) polycondensation by the employment of fluorinated phosphonates and rigid aldehyde building blocks.

  我们揭示了通过 Horner-Wadsworth-Emmons (HWE) 缩聚溶剂热合成 2D-聚(亚苯基喹喔啉亚乙烯基) (2D-PPQV) 和 2D-​​聚(亚苯基-亚乙烯基) (2D-PPV) 过程中结晶度的控制：使用氟化膦酸盐和刚性醛结构单元。