4-(2,2’-bithiophene-5-yl)-2,2‘-bipyridine | 249644-72-2

• 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-(2,2’-bithiophene-5-yl)-2,2‘-bipyridine
• 英文别名: 2-Pyridin-2-yl-4-(5-thiophen-2-ylthiophen-2-yl)pyridine
• CAS: 249644-72-2
• 化学式: C₁₈H₁₂N₂S₂
• 分子量: 320.439
• InChiKey: SVNJFGKOCRNYAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,2’-bithiophene-5-yl)-2,2‘-bipyridine 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 三甲基溴硅烷 、 溶剂黄146 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 72.25h， 生成 [5-[5-[5-[5-(2-Pyridin-2-ylpyridin-4-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]phosphonic acid
  参考文献：
  名称：

  Synthesis and Optical Properties of Bifunctional Thiophene Molecules Coordinated to Ruthenium

  摘要：

  A series of unsymmetrical bi- and tetrathiophenes have been synthesized with bipyridine and phosphonic acid functional groups. To do this, phosphonic esters were bonded to thiophenes and the thiophenes coupled to bipyridine. After synthesis of the thienylbipyridines, bis(bipyridine) ruthenium was coordinated to them through the bipyridines. The thienylbipyridines absorb visible light and fluoresce; however, on attachment to ruthenium, both their fluorescence and that of ruthenium are quenched. An additional effect of coordinating ruthenium to the thiophenes is a new absorption band around 470 nm. Variation in oligothiophene length and bipyridine substitution position allowed comparison of the effect of these variables on electronic properties. The longer oligothiophenes display lower-energy absorptions and emissions than that of the shorter thiophenes. In contrast, the position of the bipyridine attachment does not have a large effect on the absorbance or emission wavelength, or on the fluorescence quantum yield.

  DOI：

  10.1021/jo070377o
• 作为产物：
  描述：

  2,2′-二吡啶基 N-氧化物 在 四(三苯基膦)钯 乙酰溴 、 硫酸 、 硝酸 、 三溴化磷 作用下， 反应 31.0h， 生成 4-(2,2’-bithiophene-5-yl)-2,2‘-bipyridine
  参考文献：
  名称：

  Synthesis and Optical Properties of Bifunctional Thiophene Molecules Coordinated to Ruthenium

  摘要：

  A series of unsymmetrical bi- and tetrathiophenes have been synthesized with bipyridine and phosphonic acid functional groups. To do this, phosphonic esters were bonded to thiophenes and the thiophenes coupled to bipyridine. After synthesis of the thienylbipyridines, bis(bipyridine) ruthenium was coordinated to them through the bipyridines. The thienylbipyridines absorb visible light and fluoresce; however, on attachment to ruthenium, both their fluorescence and that of ruthenium are quenched. An additional effect of coordinating ruthenium to the thiophenes is a new absorption band around 470 nm. Variation in oligothiophene length and bipyridine substitution position allowed comparison of the effect of these variables on electronic properties. The longer oligothiophenes display lower-energy absorptions and emissions than that of the shorter thiophenes. In contrast, the position of the bipyridine attachment does not have a large effect on the absorbance or emission wavelength, or on the fluorescence quantum yield.

  DOI：

  10.1021/jo070377o

文献信息

• The Role of Isomeric Effects on the Luminescence Lifetimes and Electrochemistry of Oligothienyl‐Bridged Dinuclear Tris(2,2′‐bipyridine)ruthenium(II) Complexes
  作者：Robert O. Steen、Lasse J. Nurkkala、Sarah J. Angus‐Dunne、Chantal X. Schmitt、Edwin C. Constable、Mark J. Riley、Paul V. Bernhardt、Simon J. Dunne

  DOI：10.1002/ejic.200701118

  日期：2008.4

  The luminescence lifetimes (in CH 3CN at room temperature) and electrochemical potentials (in CH 3CN) of a range of mono- and bis(bidentate) 2,2′-bipyridine-capped oligothiophene-bridged Ru II comp ...

  一系列单和双（双齿）2,2'-联吡啶封端的低聚噻吩桥联 Ru II 化合物的发光寿命（室温下 CH 3CN 中）和电化学电位（CH 3CN 中）...
• Conducting redox polymers: investigations of polythiophene-Ru(bpy)3n+ hybrid materials
  作者：S. Sherry Zhu、Richard P. Kingsborough、Timothy M. Swager

  DOI：10.1039/a903193f

  日期：——

  A series of thiophene-appended Ru II (bpy) 3 derivatives, Ru(1) 3 , Ru(2) 3 , Ru(3) 3 , Ru(bpy) 2 (1), and Ru(bpy) 2 (2), and their resulting polymers have been synthesized and characterized. The bpy ligands 5,5′-bis(5-(2,2′-bithienyl))-2,2′-bipyridine, 1, 4,4′-bis(5-(2,2′-bithienyl))-2,2′-bipyridine, 2, and 4-(5-(2,2′-bithienyl))-2,2′-bipyridine, 3, all contain electrochemically polymerizable bithienyl moieties. The monomers Ru(2) 3 , Ru(3) 3 , Ru(bpy) 2 (1) and Ru(bpy) 2 (2) display spectroscopic features that are similar to the ligand-based and MLCT bands found for Ru(bpy) 3 . The cyclic voltammograms of all of these polymers display both metal-centered and thiophene-based electroactivity. High redox conductivity was found in poly(Ru(2) 3 ) and poly(Ru(3) 3 ) for both the thiophene-based oxidation and metal-based reduction processes. These results indicate that the polymers display charge localization for both the metal complexes as well as the tetrathienyl connecting units. The degree of interconnection (number of linkages) as well as the substitution pattern were found to control the conductivity of these polymers. The highest conductivity (3.3×10 –3 S cm –1 ) was found for poly(Ru(2) 3 ), which is able to have up to 6 linkages with other ruthenium complexes as well as possessing a 4,4′-substitution pattern that allows effective orbital overlap of the conjugated polymer backbone with the ruthenium centers.

  一系列附有噻吩的 Ru II (bpy) 3 衍生物，包括 Ru(1) 3、Ru(2) 3、Ru(3) 3、Ru(bpy) 2 (1) 和 Ru(bpy) 2 (2)，及其所得聚合物已被合成并表征。这些 bpy 配体 5,5′-双(5-(2,2′-双噻吩基))-2,2′-联吡啶 (1)、1,4,4′-双(5-(2,2′-双噻吩基))-2,2′-联吡啶 (2) 和 4-(5-(2,2′-双噻吩基))-2,2′-联吡啶 (3) 均含有电化学可聚合的双噻吩基基团。单体 Ru(2) 3、Ru(3) 3、Ru(bpy) 2 (1) 和 Ru(bpy) 2 (2) 表现出与 Ru(bpy) 3 的配体基和金属-配体转移 (MLCT) 带相似的光谱特征。这些聚合物的循环伏安图显示出金属中心和基于噻吩的电活性。在聚(Ru(2) 3) 和聚(Ru(3) 3) 中发现了较高的氧化还原导电性，适用于基于噻吩的氧化过程和金属基的还原过程。这些结果表明，这些聚合物在金属络合物和四噻吩连接单元上均表现出电荷局部化。连接的程度（连结数量）以及取代模式被发现会影响这些聚合物的导电性。聚(Ru(2) 3) 的导电性最高（3.3×10 –3 S cm –1），可与其他钌络合物形成多达 6 个连接，同时具备 4,4′-取代模式，使共轭聚合物主链与钌中心有效重叠。
• Diquat Based Dyes: A New Class of Photoredox Catalysts and Their Use in Aerobic Thiocyanation
  作者：Armin Meier、Sabuhi V. Badalov、Timur Biktagirov、Wolf Gero Schmidt、René Wilhelm

  DOI：10.1002/chem.202203541

  日期：——

  From diquat to dye-cat. A series of push–pull dyes using diquat as the electron-acceptor moiety have been synthesized. Their photocatalytic abilities were tested in the aerobic thiocyanation of indoles and pyrroles, giving yields of up to 97 %.

  从敌草快到染料猫。已经合成了一系列使用敌草快作为电子受体部分的推挽染料。他们的光催化能力在吲哚和吡咯的有氧硫氰化反应中进行了测试，产率高达 97%。