1,4-diethynyl-2,5-bis(trifluoromethyl)benzene | 1084895-80-6

• 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: 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene
• 英文别名: 1,4-bis(trifluoromethyl)-2,5-diethynylbenzene；HCC(p-C6H2(CF3)2)CCH；1,4-Bis(trifluoromethyl)-2,5-diethynylbenzene
• CAS: 1084895-80-6
• 化学式: C₁₂H₄F₆
• 分子量: 262.154
• InChiKey: SZWHRCFJHCPDRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  227.3±40.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-碘吡唑 、 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以84%的产率得到4,4'-{[2,5-bis(trifluoromethyl)benzene-1,4-diyl]diethyne-2,1-diyl}bis(1-Boc-pyrazole)
  参考文献：
  名称：

  高度疏水的等规孔金属-有机框架，用于捕集有害的挥发性有机化合物

  摘要：

  可调节的疏水性：可以通过在坚固的金属有机骨架（MOF）中用氟烷基残基对孔进行表面功能化并精确控制其孔径来实现防化学战剂的有效空气过滤器（见图）。即使在极端潮湿的条件下（相对湿度为80％），这些MOF也会捕获有害的挥发性有机化合物。

  DOI：

  10.1002/anie.201303484
• 作为产物：
  描述：

  1,4-bis(trifluoromethyl)-2,5-bis(trimethylsilylethynyl)benzene 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以435 mg的产率得到1,4-diethynyl-2,5-bis(trifluoromethyl)benzene
  参考文献：
  名称：

  p-Diethynylbenzene-based molecular wires, Fe–C C-p-C6H2X2–C C–Fe [Fe= Fe(η5-C5Me5)(dppe)]: Synthesis, substituent effects and unexpected formation of benzodifuran complex

  摘要：

  A series of p-diethynylbenzene- based molecular wires, Fe-C C-p-C6H2X2-C C-Fe (3) (Fe = FeCp* (dppe)), is prepared and their wire-like performance is estimated on the basis of the K-C and V-ab values. It has been revealed that electron-donating substituents (X) improve the performance. The benzodifuran complex 4 unexpectedly formed from the derivative with X = OH shows the performance comparable to 3. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.01.019

文献信息

• Highly Luminescent BODIPY-Based Organoboron Polymer Exhibiting Supramolecular Self-Assemble Structure
  作者：Atsushi Nagai、Junpei Miyake、Kenta Kokado、Yuuya Nagata、Yoshiki Chujo

  DOI：10.1021/ja806939w

  日期：2008.11.19

  A novel class of rod-coil type-organoboron polymers with p-phenylene-ethynylene as the rod segment and long alkyl chain (decyl group) as coil segment has been prepared from a Sonogashira-Hagihara coupling reaction of a BODIPY-based monomer having bis-iodophenyl and decyl groups with diyne monomers, 1,4-diethynylbenzene (a), 1,4-diethynyl-2,5bis(trifluoromethyl)benzene (b), and 2,7-diethynyl-9,9-dihexyl-9H-fluorene (c). The characterization by means of scanning electron microscopy (SEM) and transmission electron microscopy (TEM) revealed the strong tendency of the obtained polymers, 2a, 2b, and 2c, to self-assemble into particles in solution and as-casted films on a mu m-nm scale. Especially, 2a showed the presence of nm-sized particles and mu m-sized fiber-like structures formed by aggregation of each particle. Further, in CHCl3, the gelation of 2a by three-dimensional aggregation of each fiber was observed at room temperature after 24 h. Their luminescent properties showed high energy transfer efficiency from pi-conjugated polymer linkers to BODIPY moieties (Phi(F) > 71%).
• Synthesis, Characterization, and Substituent Effects of Binuclear Ruthenium Vinyl Complexes [RuCl(CO)(PMe₃)₃]₂(μ-CH═CH−Ar−CH═CH)
  作者：Xiang Hua Wu、Shan Jin、Jin Hua Liang、Zi Yong Li、Guang-ao Yu、Sheng Hua Liu

  DOI：10.1021/om900018y

  日期：2009.4.27

  A series of binuclear ruthenium vinyl complexes [RuCl(CO)(PMe3)(3)](2)(mu-CH=CH-Ar-CH=CH) (Ar = C6H4 (6a), C6H3CH3 (6b), C6H3OCH3 (6c), C6H3F (6d), C6H3Cl (6e), C6H3Br (6f), C6H3CN (6g), C6H3NO2 (6h), C6H2(CH3)(2)-2,5 (6i), C6H2(OCH3)(2)-2,5 (6i), C6H2(F)(2)-2,5 (6k), C6H2(CF3)(2)-2,5 (6l), and C6H3CF3 (6m)) have been prepared. The respective products have been characterized by elemental analyses, NMR spectrometry, and UV/vis spectrophotometry. The structures of 6h, 6i, and 6j have been established by X-ray crystallography. Electrochemical studies have revealed that intermetallic electron communication between the two Ru centers may be fine-tuned by modification of the bridging spacers, that is, by introducing one or two substituent groups on the 1,4-diethenylphenylene bridge. Electron-releasing substituents have been found to facilitate electron communication between the two metal centers.
• Highly Hydrophobic Isoreticular Porous Metal-Organic Frameworks for the Capture of Harmful Volatile Organic Compounds
  作者：Natalia M. Padial、Elsa Quartapelle Procopio、Carmen Montoro、Elena López、J. Enrique Oltra、Valentina Colombo、Angelo Maspero、Norberto Masciocchi、Simona Galli、Irena Senkovska、Stefan Kaskel、Elisa Barea、Jorge A. R. Navarro

  DOI：10.1002/anie.201303484

  日期：2013.8.5

  Tunable hydrophobicity: Efficient air filters for the protection against chemical warfare agents might be achieved by surface functionalization of the pores in robust metal–organic frameworks (MOFs) with fluoroalkyl residues and the precise control of their pore size (see picture). These MOFs capture harmful volatile organic compounds even under extremely moist conditions (80 % relative humidity).

  可调节的疏水性：可以通过在坚固的金属有机骨架（MOF）中用氟烷基残基对孔进行表面功能化并精确控制其孔径来实现防化学战剂的有效空气过滤器（见图）。即使在极端潮湿的条件下（相对湿度为80％），这些MOF也会捕获有害的挥发性有机化合物。
• p-Diethynylbenzene-based molecular wires, Fe–C C-p-C6H2X2–C C–Fe [Fe= Fe(η5-C5Me5)(dppe)]: Synthesis, substituent effects and unexpected formation of benzodifuran complex
  作者：Yumi Matsuura、Yuya Tanaka、Munetaka Akita

  DOI：10.1016/j.jorganchem.2009.01.019

  日期：2009.5

  A series of p-diethynylbenzene- based molecular wires, Fe-C C-p-C6H2X2-C C-Fe (3) (Fe = FeCp* (dppe)), is prepared and their wire-like performance is estimated on the basis of the K-C and V-ab values. It has been revealed that electron-donating substituents (X) improve the performance. The benzodifuran complex 4 unexpectedly formed from the derivative with X = OH shows the performance comparable to 3. (C) 2009 Elsevier B.V. All rights reserved.