4,7-bis((4-([2,2':6',2'']terpyridine-4'-yl)phenyl)ethynyl)[2,1,3]-benzothiadiazole | 1215875-43-6

• 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: 4,7-bis((4-([2,2':6',2'']terpyridine-4'-yl)phenyl)ethynyl)[2,1,3]-benzothiadiazole
• 英文别名: 4,7-Bis[2-[4-(2,6-dipyridin-2-ylpyridin-4-yl)phenyl]ethynyl]-2,1,3-benzothiadiazole；4,7-bis[2-[4-(2,6-dipyridin-2-ylpyridin-4-yl)phenyl]ethynyl]-2,1,3-benzothiadiazole
• CAS: 1215875-43-6
• 化学式: C₅₂H₃₀N₈S
• 分子量: 798.93
• InChiKey: XEZJVKSHXLMNMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  61
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 4'-(4-乙炔基苯基)-2,2':6',2''-三联吡啶 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到4,7-bis((4-([2,2':6',2'']terpyridine-4'-yl)phenyl)ethynyl)[2,1,3]-benzothiadiazole
  参考文献：
  名称：

  Synthesis and Characterization of New Self-Assembled Metallo-Polymers Containing Electron-Withdrawing and Electron-Donating Bis(terpyridine) Zinc(II) Moieties

  摘要：

  A series of rigid pi-conjugated bis(terpyridines) (M1-M7) bearing electron-acceptor spacer units in 4'-position was synthesized in moderate to high yields by Pd-0-catalyzed Sonogashira cross-coupling reactions. The compounds were fully characterized by NMR spectroscopy, MALDI-TOF mass spectrometry, elemental analysis and their photophysical properties were discussed in detail. These new bis(terpyridines) were applied for the self-assembly reaction with Zn-II ions to form metallo-homo polymers (P1-P7). Broadened NMR signals and UV-vis titration experiments confirmed the successful polymerization. The electro-optical properties of the materials were investigated in detail. Band gaps up to 2.08 eV and bright blue to orange photoluminescence with quantum yields of 18 to 66% were observed strongly depending on the nature of the pi-conjugated bis(terpyridine) system. In combination with electron-donor ditopic terpyridine ligands (MD1 and MD2), two Zn-II random copolymers (R1 and R2) were synthesized. These materials were investigated by UV-vis absorption and photoluminescence experiments in dilute solution and in the solid state, prepared by spin-coating from DMF Solutions. Thereby, random copolymer R2 featured an energy transfer from the donor to the acceptor part in dilute solution.

  DOI：

  10.1021/ma902110v

文献信息

• Synthesis and Characterization of New Self-Assembled Metallo-Polymers Containing Electron-Withdrawing and Electron-Donating Bis(terpyridine) Zinc(II) Moieties
  作者：Florian Schlütter、Andreas Wild、Andreas Winter、Martin D. Hager、Anja Baumgaertel、Christian Friebe、Ulrich S. Schubert

  DOI：10.1021/ma902110v

  日期：2010.3.23

  A series of rigid pi-conjugated bis(terpyridines) (M1-M7) bearing electron-acceptor spacer units in 4'-position was synthesized in moderate to high yields by Pd-0-catalyzed Sonogashira cross-coupling reactions. The compounds were fully characterized by NMR spectroscopy, MALDI-TOF mass spectrometry, elemental analysis and their photophysical properties were discussed in detail. These new bis(terpyridines) were applied for the self-assembly reaction with Zn-II ions to form metallo-homo polymers (P1-P7). Broadened NMR signals and UV-vis titration experiments confirmed the successful polymerization. The electro-optical properties of the materials were investigated in detail. Band gaps up to 2.08 eV and bright blue to orange photoluminescence with quantum yields of 18 to 66% were observed strongly depending on the nature of the pi-conjugated bis(terpyridine) system. In combination with electron-donor ditopic terpyridine ligands (MD1 and MD2), two Zn-II random copolymers (R1 and R2) were synthesized. These materials were investigated by UV-vis absorption and photoluminescence experiments in dilute solution and in the solid state, prepared by spin-coating from DMF Solutions. Thereby, random copolymer R2 featured an energy transfer from the donor to the acceptor part in dilute solution.