N-(3,5-dimethylphenyl)-3-(4-(5-hexylthiophen-2-yl)pyridin-2-yl)-1,8-naphthalimide | 1425192-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(3,5-dimethylphenyl)-3-(4-(5-hexylthiophen-2-yl)pyridin-2-yl)-1,8-naphthalimide
• 英文别名: 2-(3,5-Dimethylphenyl)-5-[4-(5-hexylthiophen-2-yl)pyridin-2-yl]benzo[de]isoquinoline-1,3-dione；2-(3,5-dimethylphenyl)-5-[4-(5-hexylthiophen-2-yl)pyridin-2-yl]benzo[de]isoquinoline-1,3-dione
• CAS: 1425192-39-7
• 化学式: C₃₅H₃₂N₂O₂S
• 分子量: 544.717
• InChiKey: UCXWTGDLRFSAMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 [RuCl2(benzene)]2 、 N-(3,5-dimethylphenyl)-3-(4-(5-hexylthiophen-2-yl)pyridin-2-yl)-1,8-naphthalimide 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以80.9%的产率得到[Ru(N-(3,5-dimethylphenyl)-3-(4-(5-hexylthiophen-2-yl)pyridin-2-yl)-1,8-naphthalimide)(MeCN)₄](PF₆)
  参考文献：
  名称：

  Ruthenium(II) Complexes Bearing a Naphthalimide Fragment: A Modular Dye Platform for the Dye-Sensitized Solar Cell

  摘要：

  Cycloruthenated complexes of the type [Ru-II(N boolean AND N)(2)(C boolean AND N)](+) (N boolean AND N = substituted 2,2 '-bipyridine; C boolean AND N = substituted 3-(2 '-pyridyl)-1,8-naphthalimide ligand) are shown to generate high power conversion efficiencies (PCEs) in the dye-sensitized solar cell (DSSC). It is shown that substitution of the pyridine ring of the C boolean AND N ligand with conjugated groups can enhance molar absorption extinction coefficients, while the electron density imparted on the metal center is alleviated by the 1,8-naphthalimide fragment. This latter feature maintains a Ru(III)/Ru(II) redox couple more positive than 0.8 V versus NHE, thereby accommodating regeneration of the oxidized dye by an iodide-based redox mediator. This dye platform can consequently be modulated at various sites to enhance light absorption and suppress recombination between the redox mediator and the TiO2 surface without compromising dye regeneration, thereby maintaining device PCEs as high as 7%. We also introduce a new phosphine-based coadsorbent, bis(2-ethylhexyl)phosphinic acid (BEPA), which is significantly easier to synthesize than the widely used bis(3,3-dimethylbutyl)phosphinic acid (DINHOP) while also facilitating high dye loading.

  DOI：

  10.1021/ic3024524
• 作为产物：
  描述：

  2-氯-4-碘吡啶 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 192.0h， 生成 N-(3,5-dimethylphenyl)-3-(4-(5-hexylthiophen-2-yl)pyridin-2-yl)-1,8-naphthalimide
  参考文献：
  名称：

  Ruthenium(II) Complexes Bearing a Naphthalimide Fragment: A Modular Dye Platform for the Dye-Sensitized Solar Cell

  摘要：

  Cycloruthenated complexes of the type [Ru-II(N boolean AND N)(2)(C boolean AND N)](+) (N boolean AND N = substituted 2,2 '-bipyridine; C boolean AND N = substituted 3-(2 '-pyridyl)-1,8-naphthalimide ligand) are shown to generate high power conversion efficiencies (PCEs) in the dye-sensitized solar cell (DSSC). It is shown that substitution of the pyridine ring of the C boolean AND N ligand with conjugated groups can enhance molar absorption extinction coefficients, while the electron density imparted on the metal center is alleviated by the 1,8-naphthalimide fragment. This latter feature maintains a Ru(III)/Ru(II) redox couple more positive than 0.8 V versus NHE, thereby accommodating regeneration of the oxidized dye by an iodide-based redox mediator. This dye platform can consequently be modulated at various sites to enhance light absorption and suppress recombination between the redox mediator and the TiO2 surface without compromising dye regeneration, thereby maintaining device PCEs as high as 7%. We also introduce a new phosphine-based coadsorbent, bis(2-ethylhexyl)phosphinic acid (BEPA), which is significantly easier to synthesize than the widely used bis(3,3-dimethylbutyl)phosphinic acid (DINHOP) while also facilitating high dye loading.

  DOI：

  10.1021/ic3024524

文献信息

• Ruthenium(II) Complexes Bearing a Naphthalimide Fragment: A Modular Dye Platform for the Dye-Sensitized Solar Cell
  作者：Dmitry V. Pogozhev、Máté J. Bezdek、Phil A. Schauer、Curtis P. Berlinguette

  DOI：10.1021/ic3024524

  日期：2013.3.18

  Cycloruthenated complexes of the type [Ru-II(N boolean AND N)(2)(C boolean AND N)](+) (N boolean AND N = substituted 2,2 '-bipyridine; C boolean AND N = substituted 3-(2 '-pyridyl)-1,8-naphthalimide ligand) are shown to generate high power conversion efficiencies (PCEs) in the dye-sensitized solar cell (DSSC). It is shown that substitution of the pyridine ring of the C boolean AND N ligand with conjugated groups can enhance molar absorption extinction coefficients, while the electron density imparted on the metal center is alleviated by the 1,8-naphthalimide fragment. This latter feature maintains a Ru(III)/Ru(II) redox couple more positive than 0.8 V versus NHE, thereby accommodating regeneration of the oxidized dye by an iodide-based redox mediator. This dye platform can consequently be modulated at various sites to enhance light absorption and suppress recombination between the redox mediator and the TiO2 surface without compromising dye regeneration, thereby maintaining device PCEs as high as 7%. We also introduce a new phosphine-based coadsorbent, bis(2-ethylhexyl)phosphinic acid (BEPA), which is significantly easier to synthesize than the widely used bis(3,3-dimethylbutyl)phosphinic acid (DINHOP) while also facilitating high dye loading.