1,4-bis[2,6-di(2-thiophenyl)pyridin-4-yl]benzene | 15645-07-5

• 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: 1,4-bis[2,6-di(2-thiophenyl)pyridin-4-yl]benzene
• 英文别名: 4,4'-(1,4-phenylene)-bis-(2,6-di(2-thienyl)pyridine)；2,6,2',6'-tetra-thiophen-2-yl-4,4'-p-phenylene-bis-pyridine；4-[4-(2,6-Dithiophen-2-ylpyridin-4-yl)phenyl]-2,6-dithiophen-2-ylpyridine
• CAS: 15645-07-5
• 化学式: C₃₂H₂₀N₂S₄
• 分子量: 560.788
• InChiKey: CULJRCUUUSCAFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  7.0
• 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：

  1,4-bis[2,6-di(2-thiophenyl)pyridin-4-yl]benzene 、 三氟甲烷磺酸甲酯 以32 %的产率得到
  参考文献：
  名称：

  具有四臂的 π 延伸紫精的分子工程，用于高效且可调谐的电致变色器件

  摘要：

  在这项工作中，以环保的方式成功合成了五种新型四臂π延伸紫精，分别表示为TPh-BMV、TMeOPh-BMV、TTh-BMV、TFPh-BMV、TBPFh-BMV 。通过在吡啶环中引入具有不同取代基的苯基，可以有效地调节光学和电化学性能。研究了基于新型紫精的一体化电致变色器件，该器件表现出高效的电致变色性能，包括高光学对比度、短响应时间、优异的循环稳定性以及高着色效率。其中，基于TBPFh-BMV的ECD在526 nm处表现出95％的极高对比度，在596 nm处表现出96％的极高对比度，以及超过350 cm 2 /C的良好着色效率。这项工作为开发 π 延伸紫精以实现高效且可调节的电致变色提供了有效的策略。

  DOI：

  10.1016/j.dyepig.2023.111556
• 作为产物：
  描述：

  1,4-苯二硼酸 在 吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 甲酸 、 1,3-双(二苯基膦)丙烷 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 乙硫醇钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.25h， 生成 1,4-bis[2,6-di(2-thiophenyl)pyridin-4-yl]benzene
  参考文献：
  名称：

  支链低聚（2-噻吩基）-和低聚（2,2'-bithien-5-基）取代的吡啶衍生物的合成和性质

  摘要：

  AbstractStarting from easily accessible precursors we describe the preparation of a series of branched oligo(2‐thienyl)‐ and oligo(2,2′‐bithienyl)‐substituted pyridine derivatives. With palladium‐catalyzed cross‐coupling reactions of pyridyl nonaflates/triflates as key steps we synthesized 2,6‐di(2‐thienyl)pyridines bridged by thiophene or benzene rings. By selective bromination of 2,6‐di(2‐thienyl)pyridine and 2,4,6‐tri(2‐thienyl)pyridine and subsequent coupling reactions an access to oligo(2,2′‐bithien‐5‐yl)‐substituted pyridine derivatives was gained. The constitution and solid state conformation of 2,6‐bis(2,2’‐bithien‐5‐yl)pyridine was determined by X‐ray analysis. This series of new pyridine‐thiophene conjugates was systematically investigated by UV/vis spectroscopy. Large Stokes shifts in the neutral and protonated form were observed. The electrochemical oxidation of two typical compounds was studied, however, these oxidations were irreversible forming a polymeric film at the anode. As a selected example, a thiophene‐bridged 2,6‐di(2‐thienyl)pyridine derivative was also investigated by scanning tunneling microscopy showing an interesting self‐assembly into a highly ordered monolayer on highly oriented pyrolytic graphite.magnified image

  DOI：

  10.1002/adsc.201300613

文献信息

• Solvent-free synthesis of new 2,4,6-triarylpyridines catalyzed by a Brønsted acidic ionic liquid as a green and reusable catalyst
  作者：Hossein Behmadi、Shima Naderipour、Seyed Mahdi Saadati、Mohammad Barghamadi、Mohammad Shaker、Niloofar Tavakoli-Hoseini

  DOI：10.1002/jhet.697

  日期：2011.9

  Some new 4‐(aryl)‐2,6‐di‐2‐naphthylpyridines and 4‐(aryl)‐2,6‐di‐2‐thienylpyridines have been prepared through three‐component condensation of 2‐acetylnaphthalene or 2‐acetylthiophene, aromatic aldehydes, and ammonium acetate in presence of 1‐(4‐sulfonylbutyl) pyridinium hydrogensulfate [(CH2)4SO3HPy][HSO4], a Brønsted acidic ionic liquid as a green and reusable catalyst in solvent‐free conditions

  通过2-乙酰基萘或2-乙酰基噻吩的三组分缩合反应制备了一些新的4-（芳基）-2,6-二-2-萘吡啶和4-（芳基）-2,6-二-2-噻吩基吡啶，芳族醛和乙酸铵，在1-（4-磺酰基丁基）吡啶鎓硫酸氢盐[（CH 2）4 SO 3 HPy] [HSO 4 ]的存在下，是布朗斯台德酸性离子液体，可在无溶剂条件下用作绿色和可重复使用的催化剂。还准备了一些新的4,4'-（1,4-亚苯基）-双-（2,6-二芳基吡啶）。J.杂环化​​学。（2011）。
• The problem of synthesizing bispyrylium salts
  作者：S. V. Krivun、G. N. Dorofeenko

  DOI：10.1007/bf00477503

  日期：——
• Synthesis and Properties of Branched Oligo(2-thienyl)- and Oligo(2,2′-bithien-5-yl)-Substituted Pyridine Derivatives
  作者：Mrinal K. Bera、Shivajirao L. Gholap、Paul Hommes、Katja Neuthe、Daniel Trawny、Jürgen P. Rabe、Dieter Lentz、Reinhold Zimmer、Hans-Ulrich Reissig

  DOI：10.1002/adsc.201300613

  日期：2013.11.25

  AbstractStarting from easily accessible precursors we describe the preparation of a series of branched oligo(2‐thienyl)‐ and oligo(2,2′‐bithienyl)‐substituted pyridine derivatives. With palladium‐catalyzed cross‐coupling reactions of pyridyl nonaflates/triflates as key steps we synthesized 2,6‐di(2‐thienyl)pyridines bridged by thiophene or benzene rings. By selective bromination of 2,6‐di(2‐thienyl)pyridine and 2,4,6‐tri(2‐thienyl)pyridine and subsequent coupling reactions an access to oligo(2,2′‐bithien‐5‐yl)‐substituted pyridine derivatives was gained. The constitution and solid state conformation of 2,6‐bis(2,2’‐bithien‐5‐yl)pyridine was determined by X‐ray analysis. This series of new pyridine‐thiophene conjugates was systematically investigated by UV/vis spectroscopy. Large Stokes shifts in the neutral and protonated form were observed. The electrochemical oxidation of two typical compounds was studied, however, these oxidations were irreversible forming a polymeric film at the anode. As a selected example, a thiophene‐bridged 2,6‐di(2‐thienyl)pyridine derivative was also investigated by scanning tunneling microscopy showing an interesting self‐assembly into a highly ordered monolayer on highly oriented pyrolytic graphite.magnified image
• Molecular engineering of π-extended viologens with four arms for efficient and tunable electrochromic devices
  作者：Yiying Han、Zhuo Gu、Yufei Pei、Peng Gao、Yu Pan、Jiayu Tao、Xiao-Peng Zhang、Jian Liu

  DOI：10.1016/j.dyepig.2023.111556

  日期：2023.11

  work, five novel π-extended viologens with four arms, denoted as TPh-BMV, TMeOPh-BMV, TTh-BMV, TFPh-BMV, TBFPh-BMV, were successfully synthesized in an eco-friendly way. By introducing phenyl groups with different substituents into the pyridine ring, the optical and electrochemical properties were tuned effectively. All-in-one electrochromic devices based on the present new viologens were investigated

  在这项工作中，以环保的方式成功合成了五种新型四臂π延伸紫精，分别表示为TPh-BMV、TMeOPh-BMV、TTh-BMV、TFPh-BMV、TBPFh-BMV 。通过在吡啶环中引入具有不同取代基的苯基，可以有效地调节光学和电化学性能。研究了基于新型紫精的一体化电致变色器件，该器件表现出高效的电致变色性能，包括高光学对比度、短响应时间、优异的循环稳定性以及高着色效率。其中，基于TBPFh-BMV的ECD在526 nm处表现出95％的极高对比度，在596 nm处表现出96％的极高对比度，以及超过350 cm 2 /C的良好着色效率。这项工作为开发 π 延伸紫精以实现高效且可调节的电致变色提供了有效的策略。