4,4'-bis(p-dimethylaminophenyl)-2,2'-bipyridine | 854049-33-5

• 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: 4,4'-bis(p-dimethylaminophenyl)-2,2'-bipyridine
• 英文别名: 4-[2-[4-[4-(dimethylamino)phenyl]pyridin-2-yl]pyridin-4-yl]-N,N-dimethylaniline
• CAS: 854049-33-5
• 化学式: C₂₆H₂₆N₄
• 分子量: 394.519
• InChiKey: ASDSUHDCEQAJHI-UHFFFAOYSA-N

物化性质

• 沸点：
  568.8±50.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硫氰酸铵 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 2,2'-联吡啶-4,4'-二甲酸 、 4,4'-bis(p-dimethylaminophenyl)-2,2'-bipyridine 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到Ru(NCS)2(4,4'-di(hydroxycarbonyl)-2,2'-bipyridine)(4,4'-bis(p-dimethylaminophenyl)-2,2'-bipyridine)
  参考文献：
  名称：

  Electronic Optimization of Heteroleptic Ru(II) Bipyridine Complexes by Remote Substituents: Synthesis, Characterization, and Application to Dye-Sensitized Solar Cells

  摘要：

  We prepared a series of new heteroleptic ruthenium(II) complexes, Ru(NCS)(2)LL' (3a-3e), where L is 4,4'-di(hydroxycarbonyl)-2,2'-bipyridine and L' is 4,4'-di(p-X-phenyl)-2,2'-pyridine (x = CN (a), F (b), H (c), OMe (d), and NMe2 (e)), in an attempt to explore the structure activity relationships in their photophysical and electrochemical behavior and in their performance in dye-sensitized solar cells (DSSCs). When substituent X is changed from electron-donating NMe2 to electron-withdrawing CN, the absorption and emission maxima reveal systematic bathochromic shifts. The redox potentials of these dyes are also significantly influenced by X. The electronic properties of the dyes were theoretically analyzed using density functional theory calculations; the results show good correlations with the experimental results. The solar-cell performance of DSSCs based on dye-grafted nanocrystalline TiO2 using 3a-3e and standard N3 (bis[(4,4'-carboxy-2,2'-bipyridine)(thiocyanato)]ruthenium(II)) were compared, revealing substantial dependences on the dye structures, particularly on the remote substituent X. The 3d-based device showed the best performance: eta = 8.30%, J(SC) = 16.0 mA center dot cm(-2), V-OC = 717 mV, and ff = 0.72. These values are better than N3-based device.

  DOI：

  10.1021/ic101909e
• 作为产物：
  描述：

  N,N'-二氧化-2,2'-联吡啶 在 乙酰溴 、 硫酸 、 硝酸 、 三溴化磷 、 sodium carbonate 作用下， 以 水 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， 反应 22.25h， 生成 4,4'-bis(p-dimethylaminophenyl)-2,2'-bipyridine
  参考文献：
  名称：

  Electronic Optimization of Heteroleptic Ru(II) Bipyridine Complexes by Remote Substituents: Synthesis, Characterization, and Application to Dye-Sensitized Solar Cells

  摘要：

  We prepared a series of new heteroleptic ruthenium(II) complexes, Ru(NCS)(2)LL' (3a-3e), where L is 4,4'-di(hydroxycarbonyl)-2,2'-bipyridine and L' is 4,4'-di(p-X-phenyl)-2,2'-pyridine (x = CN (a), F (b), H (c), OMe (d), and NMe2 (e)), in an attempt to explore the structure activity relationships in their photophysical and electrochemical behavior and in their performance in dye-sensitized solar cells (DSSCs). When substituent X is changed from electron-donating NMe2 to electron-withdrawing CN, the absorption and emission maxima reveal systematic bathochromic shifts. The redox potentials of these dyes are also significantly influenced by X. The electronic properties of the dyes were theoretically analyzed using density functional theory calculations; the results show good correlations with the experimental results. The solar-cell performance of DSSCs based on dye-grafted nanocrystalline TiO2 using 3a-3e and standard N3 (bis[(4,4'-carboxy-2,2'-bipyridine)(thiocyanato)]ruthenium(II)) were compared, revealing substantial dependences on the dye structures, particularly on the remote substituent X. The 3d-based device showed the best performance: eta = 8.30%, J(SC) = 16.0 mA center dot cm(-2), V-OC = 717 mV, and ff = 0.72. These values are better than N3-based device.

  DOI：

  10.1021/ic101909e

文献信息

• Electronic Optimization of Heteroleptic Ru(II) Bipyridine Complexes by Remote Substituents: Synthesis, Characterization, and Application to Dye-Sensitized Solar Cells
  作者：Won-Sik Han、Jung-Kyu Han、Hyun-Young Kim、Mi Jin Choi、Yong-Soo Kang、Chyongjin Pac、Sang Ook Kang

  DOI：10.1021/ic101909e

  日期：2011.4.18

  We prepared a series of new heteroleptic ruthenium(II) complexes, Ru(NCS)(2)LL' (3a-3e), where L is 4,4'-di(hydroxycarbonyl)-2,2'-bipyridine and L' is 4,4'-di(p-X-phenyl)-2,2'-pyridine (x = CN (a), F (b), H (c), OMe (d), and NMe2 (e)), in an attempt to explore the structure activity relationships in their photophysical and electrochemical behavior and in their performance in dye-sensitized solar cells (DSSCs). When substituent X is changed from electron-donating NMe2 to electron-withdrawing CN, the absorption and emission maxima reveal systematic bathochromic shifts. The redox potentials of these dyes are also significantly influenced by X. The electronic properties of the dyes were theoretically analyzed using density functional theory calculations; the results show good correlations with the experimental results. The solar-cell performance of DSSCs based on dye-grafted nanocrystalline TiO2 using 3a-3e and standard N3 (bis[(4,4'-carboxy-2,2'-bipyridine)(thiocyanato)]ruthenium(II)) were compared, revealing substantial dependences on the dye structures, particularly on the remote substituent X. The 3d-based device showed the best performance: eta = 8.30%, J(SC) = 16.0 mA center dot cm(-2), V-OC = 717 mV, and ff = 0.72. These values are better than N3-based device.