4,4'-bis[2-hydroxy-2-(phenyl)ethyl]-2,2'-bipyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,4'-bis[2-hydroxy-2-(phenyl)ethyl]-2,2'-bipyridine
• 英文别名: 4,4'-bis(2-hydroxy-2-phenylethyl)-2,2'-bipyridine；2-[2-[4-(2-Hydroxy-2-phenylethyl)pyridin-2-yl]pyridin-4-yl]-1-phenylethanol
• 化学式: C₂₆H₂₄N₂O₂
• 分子量: 396.489
• InChiKey: VSZZTLOHELNQQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-bis[2-hydroxy-2-(phenyl)ethyl]-2,2'-bipyridine 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 4,4′-diphenylethyl-2,2′-bipyridine
  参考文献：
  名称：

  New iridium cyclometallated complexes with potential application in OLED

  摘要：

  The photophysical and electrochemical properties of cyclometallic cationic iridium complexes that also contain bipyridine type ligands have been investigated in this work. The effect on the photophysical properties of the complexes on the presence of aliphatic long chain or branched substitution was analyzed. The complexes show photoluminescence maxima in the green-blue region of the visible spectrum, with acceptable quantum yields and lifetime, showing in this way potentiality to be tested in OLED devices. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.08.010
• 作为产物：
  描述：

  4,4'-二甲基-2,2'-联吡啶 在 水 、 cesium fluoride 、 lithium diisopropyl amide 作用下， 反应 1.5h， 生成 4,4'-bis[2-hydroxy-2-(phenyl)ethyl]-2,2'-bipyridine
  参考文献：
  名称：

  Synthesis of Halomethyl and Other Bipyridine Derivatives by Reaction of 4,4‘-Bis[(trimethylsilyl)methyl]-2,2‘-bipyridine with Electrophiles in the Presence of Fluoride Ion

  摘要：

  Bipyridine (bpy) ligands figure prominently in many areas of chemistry. Common precursors to many derivatives are the halomethyl-substituted analogues. This report describes a new, high yield route to these valuable compounds via a trimethylsilyl (TMS) intermediate. 4,4'-Dimethyl-2,2'-bpy was reacted with lithium diisopropylamide, and the dianion thus formed was trapped with TMSCl to generate 4,4'-bis[(trimethylsilyl)methyl]-2,2'-bp (1). The TMS group was removed using dry F- sources (TBAF/SiO2 in THF or CsF in DMF) in the presence of BrF2CCF2Br or Cl3CCCl3 to pro duce the bromide 2 or chloride 3 analogues of 4,4'-bis(halomethyl)-2,2'-bipyridine, respectively. The CsF/DMF methodology extends to other electrophiles, including benzaldehyde to give 4,4'-bis(2-hydroxy-2-phenethyl)-2,2'-bpy, 6, as well as to alkyl halides. Benzyl Br, dodecyl Br, and alpha-chloroacetonitrile gave mixtures of di- and monoalkylated products along with the diprotonated product, 4,4'-dimethyl-2,2'-bpy.

  DOI：

  10.1021/jo971685x

文献信息

• Study of the effect of aliphatic and π-conjugated systems on the photophysical properties of polypyridinic Ruthenium II complexes as potential semiconductor materials for iTMC type LEC
  作者：Felipe A. Angel、Bárbara Loeb

  DOI：10.1016/j.ica.2014.04.033

  日期：2014.9
• Influence of the Nature of the Absorption Band on the Potential Performance of High Molar Extinction Coefficient Ruthenium(II) Polypyridinic Complexes As Dyes for Sensitized Solar Cells
  作者：Francisco Gajardo、Mauricio Barrera、Ricardo Vargas、Irma Crivelli、Barbara Loeb

  DOI：10.1021/ic1020862

  日期：2011.7.4

  When tested in solar cells, ruthenium polypyridinic dyes with extended pi systems show an enhanced light-harvesting capacity that is not necessarily reflected by a high (collected electrons)/(absorbed photons) ratio. Provided that metal-to-ligand charge transfer bands, MLCT, are more effective, due to their directionality, than intraligand (IL) pi-pi* bands for the electron injection process in the solar cell, it seems important to explore and clarify the nature of the absorption bands present in these types of dyes. This article aims to elucidate if all the absorbed photons of these dyes are potentially useful in the generation of electric current. In other words, their potentiality as dyes must also be analyzed from the point of view of their contribution to the generation of excited states potentially useful for direct injection. Focusing on the assignment of the absorption bands and the nature of the emitting state, a systematic study for a series of ruthenium complexes with 4,4'-distyryl-2,2'-dipyridine (LH) and 4,4'-bis[p-(dimethylamino)-alpha-styryl]-2,2'-bipyridine (LNMe2) "chromophoric" ligands was undertaken. The observed experimental results were complemented with TDDFT calculations to elucidate the nature of the absorption bands, and a theoretical model was proposed to predict the available energy that could be injected from a singlet or a triplet excited state. For the series studied, the results indicate that the percentage of MLCT character to the anchored ligand for the lower energy absorption band follows the order [Ru(deebpy)(2)(LNMe2)](PF6)(2) > [Ru(deebpy)(2)(LH)] (PF6)(2) > [Ru(deebpy)(LH)(2)](PF6)(2), where deebpy is 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine, predicting that, at least from this point of view, their efficiency as dyes should follow the same trend.
• Synthesis of Halomethyl and Other Bipyridine Derivatives by Reaction of 4,4‘-Bis[(trimethylsilyl)methyl]-2,2‘-bipyridine with Electrophiles in the Presence of Fluoride Ion
  作者：Cassandra L. Fraser、Natia R. Anastasi、Jaydeep J. S. Lamba

  DOI：10.1021/jo971685x

  日期：1997.12.1

  Bipyridine (bpy) ligands figure prominently in many areas of chemistry. Common precursors to many derivatives are the halomethyl-substituted analogues. This report describes a new, high yield route to these valuable compounds via a trimethylsilyl (TMS) intermediate. 4,4'-Dimethyl-2,2'-bpy was reacted with lithium diisopropylamide, and the dianion thus formed was trapped with TMSCl to generate 4,4'-bis[(trimethylsilyl)methyl]-2,2'-bp (1). The TMS group was removed using dry F- sources (TBAF/SiO2 in THF or CsF in DMF) in the presence of BrF2CCF2Br or Cl3CCCl3 to pro duce the bromide 2 or chloride 3 analogues of 4,4'-bis(halomethyl)-2,2'-bipyridine, respectively. The CsF/DMF methodology extends to other electrophiles, including benzaldehyde to give 4,4'-bis(2-hydroxy-2-phenethyl)-2,2'-bpy, 6, as well as to alkyl halides. Benzyl Br, dodecyl Br, and alpha-chloroacetonitrile gave mixtures of di- and monoalkylated products along with the diprotonated product, 4,4'-dimethyl-2,2'-bpy.
• New iridium cyclometallated complexes with potential application in OLED
  作者：S. Salinas、M.A. Soto-Arriaza、B. Loeb

  DOI：10.1016/j.poly.2011.08.010

  日期：2011.11

  The photophysical and electrochemical properties of cyclometallic cationic iridium complexes that also contain bipyridine type ligands have been investigated in this work. The effect on the photophysical properties of the complexes on the presence of aliphatic long chain or branched substitution was analyzed. The complexes show photoluminescence maxima in the green-blue region of the visible spectrum, with acceptable quantum yields and lifetime, showing in this way potentiality to be tested in OLED devices. (C) 2011 Elsevier Ltd. All rights reserved.