2,9-bis(trifluoromethyl)-1,10-phenanthroline | 147315-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2,9-bis(trifluoromethyl)-1,10-phenanthroline
• 英文别名: 2,9-bis(triuoromethyl)-1,10-phenanthroline
• CAS: 147315-44-4
• 化学式: C₁₄H₆F₆N₂
• 分子量: 316.205
• InChiKey: CDSPRBQJBAAEID-UHFFFAOYSA-N

物化性质

• 沸点：
  339.3±37.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,9-bis(trifluoromethyl)-1,10-phenanthroline 、 copper(ll) bromide 在 L-ascorbic acid 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 以70%的产率得到[Cu(2,9-bis(trifluoromethyl)-1,10-phenanthroline)2]Br*H2O
  参考文献：
  名称：

  Cu^(I)(2,9-Bis(trifluoromethyl)-1,10-phenanthroline)₂⁺ Complexes:  Correlation between Solid-State Structure and Photoluminescent Properties

  摘要：

  The 90K solid-state structures, room temperature absorption, and room temperature and 17 K emission spectra of seven different salts of [Cu(I)(bfp)(2)](+) (bfp = 2,9-bis(trifluoromethyl)-1,10-phenanthroline) have been determined. To quantify the distortion of the Cu coordination environment, a distortion parameter zeta is defined that is a combined measure of the flattening, rocking, and wagging distortions of the complex cations. In general, the distortion in the (bfp) cations is less than found previously for Cu(I)(dmp)(2) (dmp = 2,9-dimethyl-1,10-phenanthroline) salts, in particular the flattening is reduced because of the bulkier 2,9-substituents. The 17 K lifetimes range up to 1.8 mus in the series of solids examined and, with the marked exception of the BF4- salt, correlate linearly with the distortion parameter zeta. The emission wavelength red-shifts with decreasing lifetime, which implies that an increased groundstate distortion is associated with a smaller energy gap.

  DOI：

  10.1021/ic049638s
• 作为产物：
  描述：

  新铜试剂 在 N-氯代丁二酰亚胺 、 三氟化锑 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 2,9-bis(trifluoromethyl)-1,10-phenanthroline
  参考文献：
  名称：

  三氟甲基化的菲咯啉配体减少了纯铜（I）配合物中的激发态畸变。

  摘要：

  我们报告了一系列具有两个，三个和四个三氟甲基官能团的纯铜（I）三氟甲基化菲咯啉配合物的合成和激发态动力学。我们对稳态吸收和发射，瞬态吸收光谱和电子结构理论的计算结果进行分析，可以对三氟甲基官能团相对于三氟甲基官能团空间位阻的增加所造成的拟Jahn-Teller畸变抑制进行深入分析。原型二甲基菲咯啉配合物。出奇，我们的结果表明，通过短暂的动力学寿命和优化的激发态观察到，通过空间位阻和稳定的1MLCT歧管的不寻常结合，通过仅2和9位三氟甲基化，可以最大程度地抑制拟Jahn-Teller变形结构。2,9-双（三氟甲基）-1,10-菲咯啉Cu（I）配合物的系统交叉（ISC）寿命为69 ps，而三重态激发态寿命和发射量子产率为106 ns和4× 10-3。菲咯啉的进一步三氟甲基化在菲咯啉氮上产生更大的σ键感应吸取力，最终导致与铜的配位较弱。最后，2,9-双（三氟甲基）-1的惊人成功

  DOI：

  10.1021/acs.inorgchem.9b03146

文献信息

• LUMINESCENT SILVER COMPLEXES
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2360162A1

  公开（公告）日：2011-08-24

  An luminescent device material which is inexpensive and exhibits excellent durability in the presence of oxygen can be provided using a luminescent silver complex which has an organic multidentate ligand, particularly, a luminescent silver complex wherein the organic multidentate ligand is coordinated to a phosphorus atom, a nitrogen atom, an oxygen atom, a sulfur atom, an arsenic atom, an oxygen anion, a nitrogen anion, or a sulfur anion, or a polymer of the luminescent silver complex.

  可以使用含有有机多齿配体的发光银配合物来提供一种在氧气存在的情况下具有极好耐久性且价格低廉的发光器件材料，特别是一种含有有机多齿配体的发光银配合物，其中有机多齿配体与磷原子、氮原子、氧原子、硫原子、砷原子、氧负离子、氮负离子或硫负离子配位，或者是该发光银配合物的聚合物。
• BIS(2,9-DI-TERT-BUTYL-1,10-PHENANTHROLINE)COPPER(I) COMPLEXES, METHODS OF SYNTHESIS, AND USES THEROF
  申请人：Burstyn Judith N.

  公开号：US20080206890A1

  公开（公告）日：2008-08-28

  The present invention provides homoleptic and heteroleptic copper(I) complexes having sterically demanding ligands, such as the bis(2,9-di-tert-butyl-1,10-phenanthroline)copper(I) complex and related complexes, methods of synthesis of these complexes and uses thereof. These copper(I) complexes are useful for various applications including photovoltaic cells, light-emitting electrochemical cells, and analyte sensor systems.

  本发明提供了具有立体位阻配体的同核和异核铜(I)配合物，例如双(2,9-二叔丁基-1,10-菲咯啉)铜(I)配合物及相关配合物，以及这些配合物的合成方法和用途。这些铜(I)配合物可用于各种应用，包括光伏电池、发光电化学电池和分析传感器系统。
• Syntheses of 2,9-bis(halomethyl-1,10-phenanthrolines: potential robust ligands for metal oxidation catalysts
  作者：Robert H. Beer、Jose Jimenez、Russell S. Drago

  DOI：10.1021/jo00059a024

  日期：1993.3

  Free radical halogenation of 2,9-dimethyl-1,10-phenanthroline with N-bromosuccinimide and N-chlorosuccinimide form the known alpha-methyl derivatives 2,9-bis(trihalomethyl)-1,10-phenanthrolines. The compound 2,9-bis(trichloromethyl)-1,10-phenanthroline can be used for one-step syntheses of oxidatively resistant fluoro- and partially reduced chloromethyl derivatives capable of coordination to metal oxidation catalysts.
• A Photoluminescent Copper(I) Complex with an Exceptionally High CuII/CuI Redox Potential: [Cu(bfp)2]+ (bfp=2,9-bis(trifluoromethyl)-1,10-phenanthroline)
  作者：Mark T. Miller、Peter K. Gantzel、Timothy B. Karpishin

  DOI：10.1002/(sici)1521-3773(19980619)37:11<1556::aid-anie1556>3.0.co;2-w

  日期：1998.6.19

  Unprecedented stabilization of the copper(I) oxidation state is demonstrated for the complex cation [Cu(bfp)2 ]+ (1) due to the steric and electronic effects of the CF3 groups (E1/2 (CuII /CuI )=+1.55 V vs. SCE). The redox existence range of the copper(I) species is remarkably high at 2.77 V. It is emissive in solution at room temperature and shows great potential as a photocatalyst; in the excited state it is a very potent photooxidant.
• LUMINESCENT SILVER COMPLEX
  申请人：Kobayashi Norifumi

  公开号：US20110309304A1

  公开（公告）日：2011-12-22

  An luminescent device material which is inexpensive and exhibits excellent durability in the presence of oxygen can be provided using a luminescent silver complex which has an organic multidentate ligand, particularly, a luminescent silver complex wherein the organic multidentate ligand is coordinated to a phosphorus atom, a nitrogen atom, an oxygen atom, a sulfur atom, an arsenic atom, an oxygen anion, a nitrogen anion, or a sulfur anion, or a polymer of the luminescent silver complex.