4,4'-bis-(6-methoxyl-2,2':6',2''-terpyridin-4'-yl)biphenyl | 1004323-30-1

• 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: 4,4'-bis-(6-methoxyl-2,2':6',2''-terpyridin-4'-yl)biphenyl
• 英文别名: 2-(6-Methoxypyridin-2-yl)-4-[4-[4-[2-(6-methoxypyridin-2-yl)-6-pyridin-2-ylpyridin-4-yl]phenyl]phenyl]-6-pyridin-2-ylpyridine；2-(6-methoxypyridin-2-yl)-4-[4-[4-[2-(6-methoxypyridin-2-yl)-6-pyridin-2-ylpyridin-4-yl]phenyl]phenyl]-6-pyridin-2-ylpyridine
• CAS: 1004323-30-1
• 化学式: C₄₄H₃₂N₆O₂
• 分子量: 676.777
• InChiKey: RMIDEMVOGHYOFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  52
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,4'-bis-(6-methoxyl-2,2':6',2''-terpyridin-4'-yl)biphenyl 、 cobalt(II) acetate 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Metallosupramolecular Polyelectrolytes Self-Assembled from Various Pyridine Ring-Substituted Bisterpyridines and Metal Ions:  Photophysical, Electrochemical, and Electrochromic Properties

  摘要：

  This work presents several metallosupramolecular coordination polyelectrolytes (MEPEs) Self-assembled from rigid, pi-conjugated, pyridine ring functionalized bisterpyridines and metal ions. The MEPEs are water-soluble and display different colors spanning the entire visible regions. Optical, electrochemical, and electrochromic properties of the obtained MEPEs are presented. The results show that the properties are profoundly affected by the nature of the substituents at the peripheral pyridine rings. Namely, MEPEs assembled from the electron-rich OMe group modified ligands exhibit high switching reversibility and stability and show a lower switching potential than the unsubstituted and electron-deficient Br-substituted analogues. The response times can be tuned either by the design of the ligands or by the choice of the metal ions to cover a broad time scale from under 1 s to several minutes. The optical memory is enhanced from 30 s to longer than 15 min as a comparison of unsubstituted and substituted MEPEs shows. Thus, the significantly enhanced stability and the ease of tuning the properties render this type of supramolecular assembly attractive as electrochromic materials for applications in a large variety of areas. Most importantly, we presented the structure-property relationships of MEPEs, which lays the groundwork for further design of new bisterpyridine-based metallosupramolecular functional materials.

  DOI：

  10.1021/ja710380a
• 作为产物：
  描述：

  4'-(4-bromophenyl)-6-methoxyl-2,2':6',2''-terpyridine 在 bis-triphenylphosphine-palladium(II) chloride potassium carbonate 、 联硼酸频那醇酯 作用下， 以 二甲基亚砜 为溶剂， 以76%的产率得到4,4'-bis-(6-methoxyl-2,2':6',2''-terpyridin-4'-yl)biphenyl
  参考文献：
  名称：

  Synthesis of π-conjugated, pyridine ring functionalized bis-terpyridines with efficient green, blue, and purple emission

  摘要：

  A large variety of rigid, pi-conjugated, pyridine ring functionalized bis-terpyridines are synthesized efficiently using tandem Miyaura/Suzuki-type cross-coupling reaction. Photophysical property study reveals that the absorption and luminescent properties of the obtained bis-terpyridines are profoundly affected by the nature of the functional groups at the peripheral pyridine and the spacers. Namely, by tailoring precisely the Structures, the light-emitting efficiencies of bis-terpyridines can be enhanced significantly with quantum yields (phi(f)) of up to 0.62, and the emission colors can be tuned to display distinct colors including purple, bright blue, and bright green. Consequently, the novel bis-terpyridines are attractive ligands for the assembly of new metallo-supramolecule based functional materials. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.106

文献信息

• Fluorescent colour modulation in Zn(ii)-based metallo-supramolecular polymer films by electronic-state control of the ligand
  作者：Takashi Sato、Rakesh K. Pandey、Masayoshi Higuchi

  DOI：10.1039/c3dt51354h

  日期：——

  A series of Zn(II)-based metallo-supramolecular polymers were prepared by 1 : 1 complexation of Zn(ClO4)2 and bis(terpyridine)s with electron-donating (alkoxy) or electron-withdrawing (cyano) groups at the 6-position of the peripheral pyridine moiety. The Zn(II)-based polymers displayed relatively high quantum yields (ΦPL = 0.68–0.76) in solution at room temperature. More importantly, they showed different luminescent colours of blue, cyan, and green in the film state, because of the large Stokes shift caused by the substituent effect of the ligand.

  通过Zn(ClO4)2和双(三联吡啶)在6位外围吡啶部分与电子给体（烷氧基）或电子吸引体（氰基）1：1络合，制备了一系列Zn(II)基金属超分子聚合物。Zn(II)基聚合物在室温溶液中显示出相对较高的量子产额（ΦPL = 0.68-0.76）。更重要的是，由于配体的取代效应导致斯托克斯位移较大，它们在薄膜状态下显示出蓝色、青色和绿色的不同发光颜色。
• Synthesis of π-conjugated, pyridine ring functionalized bis-terpyridines with efficient green, blue, and purple emission
  作者：Fu-She Han、Masayoshi Higuchi、Dirk G. Kurth

  DOI：10.1016/j.tet.2008.06.106

  日期：2008.9

  A large variety of rigid, pi-conjugated, pyridine ring functionalized bis-terpyridines are synthesized efficiently using tandem Miyaura/Suzuki-type cross-coupling reaction. Photophysical property study reveals that the absorption and luminescent properties of the obtained bis-terpyridines are profoundly affected by the nature of the functional groups at the peripheral pyridine and the spacers. Namely, by tailoring precisely the Structures, the light-emitting efficiencies of bis-terpyridines can be enhanced significantly with quantum yields (phi(f)) of up to 0.62, and the emission colors can be tuned to display distinct colors including purple, bright blue, and bright green. Consequently, the novel bis-terpyridines are attractive ligands for the assembly of new metallo-supramolecule based functional materials. (C) 2008 Elsevier Ltd. All rights reserved.
• Metallosupramolecular Polyelectrolytes Self-Assembled from Various Pyridine Ring-Substituted Bisterpyridines and Metal Ions:  Photophysical, Electrochemical, and Electrochromic Properties
  作者：Fu She Han、Masayoshi Higuchi、Dirk G. Kurth

  DOI：10.1021/ja710380a

  日期：2008.2.1

  This work presents several metallosupramolecular coordination polyelectrolytes (MEPEs) Self-assembled from rigid, pi-conjugated, pyridine ring functionalized bisterpyridines and metal ions. The MEPEs are water-soluble and display different colors spanning the entire visible regions. Optical, electrochemical, and electrochromic properties of the obtained MEPEs are presented. The results show that the properties are profoundly affected by the nature of the substituents at the peripheral pyridine rings. Namely, MEPEs assembled from the electron-rich OMe group modified ligands exhibit high switching reversibility and stability and show a lower switching potential than the unsubstituted and electron-deficient Br-substituted analogues. The response times can be tuned either by the design of the ligands or by the choice of the metal ions to cover a broad time scale from under 1 s to several minutes. The optical memory is enhanced from 30 s to longer than 15 min as a comparison of unsubstituted and substituted MEPEs shows. Thus, the significantly enhanced stability and the ease of tuning the properties render this type of supramolecular assembly attractive as electrochromic materials for applications in a large variety of areas. Most importantly, we presented the structure-property relationships of MEPEs, which lays the groundwork for further design of new bisterpyridine-based metallosupramolecular functional materials.