4,4'-bis(4-methoxyphenyl)-2,2'-bipyridine | 254450-32-3

• 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(4-methoxyphenyl)-2,2'-bipyridine
• 英文别名: 4,4'-bis(p-methoxyphenyl)-2,2'-bipyridine；4-(4-Methoxyphenyl)-2-[4-(4-methoxyphenyl)pyridin-2-yl]pyridine；4-(4-methoxyphenyl)-2-[4-(4-methoxyphenyl)pyridin-2-yl]pyridine
• CAS: 254450-32-3
• 化学式: C₂₄H₂₀N₂O₂
• 分子量: 368.435
• InChiKey: QTZMNWJEIGCVGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-bis(4-methoxyphenyl)-2,2'-bipyridine 、 (4-(p-methoxyphenyl)-2,2’:6’,2’’-terpyridine)RuCl3 在 三乙胺 、 lithium chloride 作用下， 以 乙二醇 为溶剂， 反应 8.0h， 以82%的产率得到[Ru^II(4'-(4-methoxyphenyl)-2,2':6',2''-terpyridine)(4,4'-bis(4-methoxyphenyl)-2,2'-bipyridine)Cl](Cl)
  参考文献：
  名称：

  一系列钌-亚硝酰基络合物中的一氧化氮（NO）光释放：寻找全面机理的新实验见解†

  摘要：

  由[Ru（terpy）（bipy）（NO）] 3+核（terpy是2,2'：6'，2''-terpyridine和bipy是2,2'构成的一系列四个钌（II）配合物-联吡啶）进行了研究。它们的区别在于，在吡啶片段的不同位置引入了零个，一个，两个或三个4'-（4-甲氧基苯基）（MP）电子给体取代基，以增加分子内电荷向强吸收亚硝酰基（NO）的转移能力）配体。紫外可见光谱反映了配合物中MP取代基的存在和位置。对于含有4'-（MP）-terpy配体的物种，低位跃迁被确定为是由4'-（MP）-terpy到Ru（NO）分子内电荷转移引起的，TD进一步证实了这一点。 -DFT分析。辐照于λ = 436 nm，对于不同的配合物，该孤立的跃迁导致NO光释放的量子产率等于0.002和0.011，比率为6（而不是1），这可以明确地得出一个单电子跃迁无法解释的结论用于NO释放机制。

  DOI：

  10.1039/c8nj03907k
• 作为产物：
  描述：

  4,4'-二溴-2,2'-联吡啶1,1'-二氧化物 在 三溴化磷 、 sodium carbonate 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 18.25h， 生成 4,4'-bis(4-methoxyphenyl)-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

• Effect of electron-donor ancillary ligands on the heteroleptic ruthenium complexes: synthesis, characterization, and application in high-performance dye-sensitized solar cells
  作者：Wang-Chao Chen、Fan-Tai Kong、Xue-Peng Liu、Fu-Ling Guo、Li Zhou、Yong Ding、Zhao-Qian Li、Song-Yuan Dai

  DOI：10.1039/c6cp00541a

  日期：——

  Three heteroleptic ruthenium complexes, RC-15, RC-16 and RC-22, with sulfur- or oxygen-containing electron-donor, phenylpyridine-based ancillary ligands, are synthesized. The influence of the different electron donors—the acyclic electron donors methylthio and methoxyl, and the cyclic electron donor methylenedioxy—on the photophysical and electrochemical behavior in dye sensitizers and photovoltaic

  合成了三种杂合钌络合物RC-15，RC-16和RC-22，它们具有含硫或含氧电子给体，基于苯基吡啶的辅助配体。研究了不同电子给体（无环电子给体甲硫基和甲氧基，以及环状电子给体亚甲二氧基）对染料敏化剂中光物理和电化学行为以及DSSC中光伏性能的影响。与常规染料N3相比，所有染料均表现出优异的性能，表现为摩尔吸收率，光电流密度（J SC）和转化效率（η）。基于RC-15和RC-16在无环电子给体中只有两个原子的变化，显示出类似的光伏性能（RC-15的9.28％和RC-16的9.32％）。RC-22记录到最高光电流密度（19.06 mA cm -2）和转换效率（9.74％），其中包含环状电子给体。进行瞬态吸收（TAS）和时间分辨光致发光（TRPL）测量以研究敏化剂的再生和激发电子衰变动力学的行为。此外，电化学阻抗谱（EIS）用于解释电荷复合和电子寿命。这些结果揭示了对电子给体辅助配体的不同构型的实质依赖性。
• Structure–Property Relationship in Amber Color Light-Emitting Electrochemical Cell with TFSI Counteranion: Enhancing Device Performance by Different Substituents on N^∧N Ligand
  作者：Nuriye Demir、Merve Karaman、Gul Yakali、Tugba Tugsuz、Serpil Denizalti、Serafettin Demic、Bircan Dindar、Mustafa Can

  DOI：10.1021/acs.inorgchem.0c02939

  日期：2021.4.5

  photoluminescence intensity was observed in complex 2bTFSI compared to other complexes in the solid state. Their theoretical absorption and phosphorescence emission transitions in acetonitrile were also investigated by using double- and triple-ζ basis sets with B3LYP and PBE0 hybrid functional. The best light-emitting electrochemical cell (LEC) performance was exhibited by complex 2bTFSI, and the data obtained were

  合成了琥珀色的新型Ir（III）配合物：[Ir（Meppy）2（Fpbpy）] [PF 6 ]（1b PF 6），[Ir（Meppy）2（Fpbpy）] [TFSI]（1b TFSI）， [Ir（Meppy）2（MeObpy）] [PF 6 ]（2b PF 6）和[Ir（Meppy）2（MeObpy）] [TFSI]（2b TFSI），其中Meppy = 2-（对-甲基苯基）-吡啶（b），Fpbpy ＝ 4，4′-双（4-氟苯基）-2，2′-联吡啶（1），MeObpy ＝ 4，4′-双（4-甲氧基）-2，2′-联吡啶（2个）。光物理和X射线结果表明，该配合物具有聚集诱导的磷光发射（AIPE）和盐诱导的多态性效应。与固态的其他配合物相比，在配合物2b TFSI中观察到最高的光致发光强度。通过使用具有B3LYP和PBE0杂合功能的双和三ζ基集，还研究了它们在乙腈中的理论吸收和磷光发射跃迁。复杂的2b
• 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.
• Nitric oxide (NO) photo-release in a series of ruthenium–nitrosyl complexes: new experimental insights in the search for a comprehensive mechanism
  作者：Max Roose、Marine Tassé、Pascal G. Lacroix、Isabelle Malfant

  DOI：10.1039/c8nj03907k

  日期：——

  A series of four ruthenium(II) complexes built from the [Ru(terpy)(bipy)(NO)]3+ core (terpy is 2,2′:6′,2′′-terpyridine and bipy is 2,2′-bipyridine) are investigated. They differ by the presence of zero, one, two, or three 4′-(4-methoxyphenyl) (MP) electron donor substituents introduced at different positions on the pyridine fragments to increase the intramolecular charge transfer capabilities towards

  由[Ru（terpy）（bipy）（NO）] 3+核（terpy是2,2'：6'，2''-terpyridine和bipy是2,2'构成的一系列四个钌（II）配合物-联吡啶）进行了研究。它们的区别在于，在吡啶片段的不同位置引入了零个，一个，两个或三个4'-（4-甲氧基苯基）（MP）电子给体取代基，以增加分子内电荷向强吸收亚硝酰基（NO）的转移能力）配体。紫外可见光谱反映了配合物中MP取代基的存在和位置。对于含有4'-（MP）-terpy配体的物种，低位跃迁被确定为是由4'-（MP）-terpy到Ru（NO）分子内电荷转移引起的，TD进一步证实了这一点。 -DFT分析。辐照于λ = 436 nm，对于不同的配合物，该孤立的跃迁导致NO光释放的量子产率等于0.002和0.011，比率为6（而不是1），这可以明确地得出一个单电子跃迁无法解释的结论用于NO释放机制。