5,5'-bis([2,2'-bithiophen]-5-yl)-2,2'-bipyridine | 181312-64-1

• 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: 5,5'-bis([2,2'-bithiophen]-5-yl)-2,2'-bipyridine
• 英文别名: 5,5'-bis(2,2'-bithiophene-5-yl)-2,2'-bipyridine；5,5'-bis(2,2'-bithiophen-5-yl)-2,2'-bipyridine；5,5'-bis(5-(2,2'-bithienyl))-2,2'-bipyridine；4,4'-bis(2,2-dithien-2-yl)-2,2'-bipyridine；5,5'-Di([2,2'-bithiophen]-5-yl)-2,2'-bipyridine；5-(5-thiophen-2-ylthiophen-2-yl)-2-[5-(5-thiophen-2-ylthiophen-2-yl)pyridin-2-yl]pyridine
• CAS: 181312-64-1
• 化学式: C₂₆H₁₆N₂S₄
• 分子量: 484.69
• InChiKey: PGVUNEJHZOTOFP-UHFFFAOYSA-N

物化性质

• 沸点：
  674.2±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-bis([2,2'-bithiophen]-5-yl)-2,2'-bipyridine 在 ammonium hexafluorophosphate 作用下， 以 水 为溶剂， 反应 96.0h， 生成 3,10-bis(2,2'-bithiophene-5-yl)-6,7-dihydropyrido[1,2-a:2',1'-c]pyrazinodiynium hexafluorophosphate
  参考文献：
  名称：

  An electrochromic diquat-quaterthiophene alternating copolymer: A polythiophene with a viologen-like moiety in the main chain

  摘要：

  A bis-bithiophenyl derivative of diquat, 3,10-bis(2,2'-bithiophene-5-yl)-6,7-dihydropyrido[1,2-a:2',1'-c]pyrazinodiynium hexafluorophosphate (bt2dq), was synthesized by quaternization of 5,5 ''-bis(2,2'-bithiophene-5-yl)-2,2'-bipyridine with 1,2-dibromoethane. Its UV-vis absorption spectrum is explained by TD-DFT calculations. It shows the electrochemical properties characteristic for bipyridinium salts (viologens and diquats) and can be electropolymerized to form a conjugated polymer composed of alternating quaterthiophene and diquat blocks. The polymer has been characterised by cyclic voltammetry and UV-vis spectroelectrochemistry: it can be reversibly oxidized, with spectral signs of p-doping of the oligothiophene blocks, and reversibly reduced, with formation of viologen-like cation radicals, which dimerize or form pi-stacks. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2011.05.132
• 作为产物：
  描述：

  5,5'-二溴-2,2'-联吡啶 、 2-(tri-n-butyl)stannyl-5,2'-bithiophene 在 trans-dichlorobis(triphenylphosphine)palladium(II) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以60%的产率得到5,5'-bis([2,2'-bithiophen]-5-yl)-2,2'-bipyridine
  参考文献：
  名称：

  导电多金属轮烷：金属离子介导的电导率和电荷定位增强

  摘要：

  在本文中，我们描述了两种金属轮烷系统 Rot(1,M) 和 Rot(2,M)（M = Zn2+ 或 Cu1+）的聚合物，它们是通过络合大环菲咯啉、5,5'-双（[ 2,2'-联噻吩]-5-基)-2,2'-联吡啶（配体 1）或 5,5'-双(3,4:3',4'-双(亚乙基二氧基)[2,2' -bithiophen]-5-yl)-2,2'-联吡啶（配体 2）和 Zn2+ 或 Cu1+ 离子。相应的多金属轮烷 PolyRot(1,M) 和 PolyRot(2,M) 是通过 Rot(1,M) 和 Rot(2,M) 的氧化聚合产生的。报告了对金属轮烷和多金属轮烷以及相关非轮烷聚合物 Poly(1) 和 Poly(2) 的电化学、导电和光学性质的研究。PolyRot(1,M) 和 PolyRot(2,M) 的电化学和电导率联合研究表明，聚金属轮烷' s 氧化还原和导电性能受配位金属离子的路易斯酸性和氧

  DOI：

  10.1021/ja972794w

文献信息

• Conducting Polymetallorotaxanes:  Metal Ion Mediated Enhancements in Conductivity and Charge Localization
  作者：S. Sherry Zhu、Timothy M. Swager

  DOI：10.1021/ja972794w

  日期：1997.12.1

  2‘-bithiophen]-5-yl)-2,2‘-bipyridine (ligand 2), and Zn2+ or Cu1+ ions. The corresponding polymetallorotaxanes, PolyRot(1,M) and PolyRot(2,M), are produced by oxidative polymerization of Rot(1,M) and Rot(2,M). The investigations of the electrochemical, conducting, and optical properties of the metallorotaxanes and polymetallorotaxanes as well as related nonrotaxane polymers Poly(1) and Poly(2) are reported

  在本文中，我们描述了两种金属轮烷系统 Rot(1,M) 和 Rot(2,M)（M = Zn2+ 或 Cu1+）的聚合物，它们是通过络合大环菲咯啉、5,5'-双（[ 2,2'-联噻吩]-5-基)-2,2'-联吡啶（配体 1）或 5,5'-双(3,4:3',4'-双(亚乙基二氧基)[2,2' -bithiophen]-5-yl)-2,2'-联吡啶（配体 2）和 Zn2+ 或 Cu1+ 离子。相应的多金属轮烷 PolyRot(1,M) 和 PolyRot(2,M) 是通过 Rot(1,M) 和 Rot(2,M) 的氧化聚合产生的。报告了对金属轮烷和多金属轮烷以及相关非轮烷聚合物 Poly(1) 和 Poly(2) 的电化学、导电和光学性质的研究。PolyRot(1,M) 和 PolyRot(2,M) 的电化学和电导率联合研究表明，聚金属轮烷' s 氧化还原和导电性能受配位金属离子的路易斯酸性和氧
• Conducting Polymetallorotaxanes:  A Supramolecular Approach to Transition Metal Ion Sensors
  作者：S. Sherry Zhu、Patrick J. Carroll、Timothy M. Swager

  DOI：10.1021/ja9619667

  日期：1996.1.1

  receptors into conducting polymer frameworks has been shown to produce efficient resistive and fluorescence responses to targeted analytes.1 Conducting polymers that contain transition metals also present opportunities to generate a variety of new sensory functions as well as conduction by mixed valence processes.2 As part of our continuing interest in sensory polymers, we have targeted conducting polymers

  受体与导电聚合物框架的整合已被证明可以对目标分析物产生有效的电阻和荧光响应。 1 含有过渡金属的导电聚合物也提供了产生各种新感觉功能以及通过混合价过程传导的机会。 2作为我们对感官聚合物的持续兴趣的一部分，我们将目标定为含有金属轮烷的导电聚合物。3,4 在本次通讯中，我们报告了新型导电聚金属轮烷和相应的无金属聚轮烷。我们进一步证明这些聚轮烷可逆地结合 Cu+ 和 Zn2+ 离子，并且螺纹轮烷结构对于产生良好的可逆络合至关重要。选择化合物 2（方案 1）作为穿线和聚合元素，因为我们最近证明了其在形成导电聚合物-过渡金属杂化材料方面的实用性。2 此外，我们已经确定无金属聚合物 Poly(2) 显示氧化和还原形式的导电性窗口。2 金属轮烷单体 3 和 4 通过将 Sauvage 开发的大环菲咯啉 1 4 2 与 CH2Cl2 中的 Cu+ 或 Zn2+ 离子 (1:1:1) 结合起来很容易组装（
• Three-Strand Conducting Ladder Polymers: Two-Step Electropolymerization of Metallorotaxanes
  作者：Julio Buey、Timothy M. Swager

  DOI：10.1002/(sici)1521-3773(20000204)39:3<608::aid-anie608>3.0.co;2-w

  日期：2000.2.4

  Sequential polymerization of supramolecular metallorotaxane complexes results in three-stranded conducting ladder polymers. The internal polymer is "sandwiched" between the other two polymers to give molecular wires that are effectively insulated when the outer polymers are in their nonconducting state (shown schematically). The intermolecular conductivity can be mediated by the Cu(1+)/Cu(2+) redox couple.
• An electrochromic diquat-quaterthiophene alternating copolymer: A polythiophene with a viologen-like moiety in the main chain
  作者：M. Krompiec、I. Grudzka、M. Filapek、Ł. Skórka、S. Krompiec、M. Łapkowski、M. Kania、W. Danikiewicz

  DOI：10.1016/j.electacta.2011.05.132

  日期：2011.10

  A bis-bithiophenyl derivative of diquat, 3,10-bis(2,2'-bithiophene-5-yl)-6,7-dihydropyrido[1,2-a:2',1'-c]pyrazinodiynium hexafluorophosphate (bt2dq), was synthesized by quaternization of 5,5 ''-bis(2,2'-bithiophene-5-yl)-2,2'-bipyridine with 1,2-dibromoethane. Its UV-vis absorption spectrum is explained by TD-DFT calculations. It shows the electrochemical properties characteristic for bipyridinium salts (viologens and diquats) and can be electropolymerized to form a conjugated polymer composed of alternating quaterthiophene and diquat blocks. The polymer has been characterised by cyclic voltammetry and UV-vis spectroelectrochemistry: it can be reversibly oxidized, with spectral signs of p-doping of the oligothiophene blocks, and reversibly reduced, with formation of viologen-like cation radicals, which dimerize or form pi-stacks. (C) 2011 Elsevier Ltd. All rights reserved.