2-(2-pyridinyl)-4-(1H-pyrrol-1-yl)pyridine | 805229-09-8

• 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: 2-(2-pyridinyl)-4-(1H-pyrrol-1-yl)pyridine
• 英文别名: 4-(1H-pyrrol-1-yl)-2,2'-bipyridine；pyrr-bpy；pyrrbpy；4-(1H-Pyrrol-1-yl)--2,2'-bipyridine；2-pyridin-2-yl-4-pyrrol-1-ylpyridine
• CAS: 805229-09-8
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: CFVCUTBPMWHETK-UHFFFAOYSA-N

物化性质

• 沸点：
  415.0±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  水合三氯化钌 、 2-(2-pyridinyl)-4-(1H-pyrrol-1-yl)pyridine 在 N-乙基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [Ru(pyrr-bpy)2Cl2]
  参考文献：
  名称：

  Dye-sensitized solar cells based on PEDOP as a hole conductive medium

  摘要：

  Dye-sensitized photo-electrochemical cells based on a solid poly-(3,4-(ethylenedioxy)pyrrole) (PEDOP) electron mediating matrix were assembled and photo-electrochemically characterized. The conductive polymer was directly grown on the sensitized TiO2 surface exploiting a photo-assisted electropolymerization promoted by a properly designed ruthenium dye bearing pyrrole functionalities. J-V characteristics and photoaction spectra indicated very low efficiencies mainly determined by an efficient recombination of photo-injected electrons with both PEDOP acceptor states and oxidized sensitizers. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2007.04.016
• 作为产物：
  描述：

  4-氨基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 正丁基锂 、 N,N-二甲基乙醇胺 、 溶剂黄146 、 三苯基膦 作用下， 以 正己烷 、 甲苯 、 xylene 为溶剂， 反应 13.5h， 生成 2-(2-pyridinyl)-4-(1H-pyrrol-1-yl)pyridine
  参考文献：
  名称：

  4-（1 H -1-吡咯基）吡啶的选择性锂化。获得新的电子释放配体

  摘要：

  已经实现了4-（1 H -1-吡咯基）吡啶的第一次锂化。通过利用吡咯核的电子给体效应，使用含有BuLi的锂聚集体诱导了选择性吡啶环官能化。将适当的取代基α引入吡啶氮中，得到新的电子富集的吡啶基膦，联吡啶和三联吡啶配体。

  DOI：

  10.1021/jo0496244

文献信息

• A Unified Approach to Couple Aromatic Heteronucleophiles to Azines and Pharmaceuticals
  作者：Ryan G. Anderson、Brianna M. Jett、Andrew McNally

  DOI：10.1002/anie.201807322

  日期：2018.9.17

  Coupling aromatic heteronucleophiles to arenes is a common way to assemble drug‐like molecules. Many methods operate via nucleophiles intercepting organometallic intermediates, via Pd‐, Cu‐, and Ni‐catalysis, that facilitate carbon‐heteroatom bond formation and a variety of protocols. We present an alternative, unified strategy where phosphonium salts can replicate the behavior of organometallic intermediates

  将芳香族异核试剂与芳烃偶联是组装类药物分子的常见方法。许多方法通过亲核试剂拦截有机金属中间体，通过 Pd、Cu 和 Ni 催化来进行，从而促进碳杂原子键的形成和各种方案。我们提出了一种替代的、统一的策略，其中鏻盐可以复制有机金属中间体的行为。在一组狭窄的反应条件下，多种芳香族杂核亲核试剂可以与吡啶和二嗪偶联，这在金属催化偶联中经常出现问题，例如在具有多个极性官能团的复杂结构中无法获得（假）卤化物前体。
• New Ruthenium Complexes with 4‐(1 <i>H</i> ‐Pyrrol‐1‐yl)‐Substituted Polypyridine Ligands − Electrochemical and Spectroscopic Properties
  作者：David Martineau、Philippe Gros、Marc Beley、Yves Fort

  DOI：10.1002/ejic.200400385

  日期：2004.10

  new pyrrole-containing ligands and their ruthenium complexes have been prepared. The pyrrole ring bound by nitrogen to pyridine was found to significantly modify photophysical and electrochemical properties compared to parent bi- and terpyridines. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  制备了三种新的含吡咯配体及其钌配合物。发现与母体双吡啶和三联吡啶相比，通过氮与吡啶结合的吡咯环显着改变了光物理和电化学性质。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Homoleptic Ruthenium Complex Bearing Dissymmetrical 4-Carboxy-4′-pyrrolo-2,2′-bipyridine for Efficient Sensitization of TiO₂ in Solar Cells
  作者：Arnald Grabulosa、Marc Beley、Philippe C. Gros、Silvia Cazzanti、Stefano Caramori、Carlo A. Bignozzi

  DOI：10.1021/ic9009256

  日期：2009.8.17

  An easily accessible homoleptic complex [Ru(L3)(3)](2+) containing a dissymmetrical bipyridine (1-3) substituted by a pyrrole and a carboxylic group has been evaluated in a dye-sensitized solar cell. The new dye displayed extended absorption domain, high absorbance, and a promising 65% IPCE value. Higher scores were reached using a cobalt-iron mediator instead of the usual LiI/I-2 couple for regeneration of the Ru-II state. Transient absorption spectroscopy was used to explain the mediator effect.
• Tuning of Ruthenium Complex Properties Using Pyrrole- and Pyrrolidine-Containing Polypyridine Ligands
  作者：David Martineau、Marc Beley、Philippe C. Gros、Silvia Cazzanti、Stefano Caramori、Carlo A. Bignozzi

  DOI：10.1021/ic062042f

  日期：2007.3.1

  The effect of pyrrole- and pyrrolidine-containing ligands (L) on the properties of heteroleptic [RuL(2)dcbpy](2+) complexes has been investigated. TiO2 electrodes modified with the new complexes exhibited extended absorption domains and high absorbances. Providing that a cobalt-based mediator was used for regeneration of the Ru-II state, good incident photon-to-current efficiency (near 80%) values were obtained in the pyrrole series.