2-[2,5-Dimethyl-4-(6-pyridin-2-ylpyridin-3-yl)phenyl]anthracene-9,10-dione | 1337570-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[2,5-Dimethyl-4-(6-pyridin-2-ylpyridin-3-yl)phenyl]anthracene-9,10-dione
• 英文别名: 2-[2,5-dimethyl-4-(6-pyridin-2-ylpyridin-3-yl)phenyl]anthracene-9,10-dione
• CAS: 1337570-10-1
• 化学式: C₃₂H₂₂N₂O₂
• 分子量: 466.539
• InChiKey: QEKIVPHKXNGZJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2,5-Dimethyl-4-(6-pyridin-2-ylpyridin-3-yl)phenyl]anthracene-9,10-dione 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Photoinduced Electron Transfer in Rhenium(I)–Oligotriarylamine Molecules

  摘要：

  Two molecular triads with an oligotriarylamine multielectron donor were synthesized and investigated with a view to obtaining charge-separated states in which the oligotriarylamine is oxidized 2-fold. Such photoinduced accumulation of multiple redox equivalents is of interest for artificial photosynthesis. The first triad was comprised of the oligotriarylamine and two rhenium(I) tricarbonyl diimine photosensitizers each of which can potentially accept one electron. In the second triad the oligotriarylamine was connected to anthraquinone, in principle an acceptor of two electrons, via a rhenium(I) tricarbonyl diimine unit. With nanosecond transient absorption spectroscopy (using an ordinary pump-probe technique) no evidence for the generation of 2-fold oxidized oligotriarylamine or 2-fold reduced anthraquinone was found. The key factors limiting the photochemistry of the new triads to simple charge separation of one electron and one hole are discussed, and the insights gained from this study are useful for further research in the area of charge accumulation in purely molecular (nanoparticle-free) systems. An important problem of the rhenium-based systems considered here is the short wavelength required for photoexcitation. In the second triad, photogenerated anthraquinone monoanion is protonated by organic acids, and the resulting semiquinone species leads to an increase in lifetime of the charge-separated state by about an order of magnitude. This shows that the proton-coupled electron transfer chemistry of quinones could be beneficial for photoinduced charge accumulation.

  DOI：

  10.1021/ic501620g
• 作为产物：
  描述：

  2-(2,5-dimethyl-4-(trimethylsilyl)phenyl)anthracene-9,10-dione 在 四(三苯基膦)钯 、 一氯化碘 作用下， 以 二氯甲烷 、 间二甲苯 为溶剂， 生成 2-[2,5-Dimethyl-4-(6-pyridin-2-ylpyridin-3-yl)phenyl]anthracene-9,10-dione
  参考文献：
  名称：

  共价钌-蒽醌二联体中的光诱导电子转移：驱动力，溶剂极性和施主-桥能隙的相对重要性†

  摘要：

  四个由Ru（bpy）3 2+（py = 2,2'-联吡啶）合成了光敏剂，9,10-蒽醌电子受体和连接两个氧化还原伙伴的分子桥，并通过光谱学和电化学方法进行了研究。试图评估驱动力，溶剂极性和桥变异对这些分子中光诱导电子转移速率的相对重要性。预期地，在钌络合物的联吡啶配体中引入叔丁基取代基，并改变溶剂二氯甲烷 到 乙腈导致电荷传输速率的显着加速。在二氯甲烷因此，光诱导的电子转移与光敏剂固有的激发态失活过程没有竞争性。在乙腈通过将叔丁基取代基连接到bpy辅助配体上，驱动力增加了0.2 eV，导致电子传递速率增加了一个数量级。用对二甲氧基苯间隔基代替对二甲苯桥，使电荷转移速率加速了3.5倍。因此，在这项研究的二元组中，各个因素对电子传输速率的重要性的相对顺序如下：溶剂极性≥驱动力>供体-桥能隙。

  DOI：

  10.1039/c2cp23240e

文献信息

• Microsecond charge recombination in a linear triarylamine–Ru(bpy)32+–anthraquinone triad
  作者：Jihane Hankache、Oliver S. Wenger

  DOI：10.1039/c1cc13831f

  日期：——

  Linear triads with ruthenium photosensitizers are frequently based on the Ru(terpyridine)(2)(2+) unit. We report on vectorial photoinduced electron transfer in a linear triad based on the Ru(bipyridine)(3)(2+) photosensitizer. Electron-hole separation over a 22 A-distance is established with a quantum yield greater than 64% and persists for 1.3 mus in acetonitrile.

  带有钌光敏剂的线性三联体通常基于Ru（terpyridine）（2）（2+）单元。我们报告了基于Ru（bipyridine）（3）（2+）光敏剂的线性三元组中的矢量光诱导电子转移。建立了22 A距离的电子-空穴分离，量子产率大于64％，并在乙腈中持续1.3亩。
• Photoinduced electron transfer in covalent ruthenium–anthraquinone dyads: relative importance of driving-force, solvent polarity, and donor–bridge energy gap
  作者：Jihane Hankache、Oliver S. Wenger

  DOI：10.1039/c2cp23240e

  日期：——

  increase in electron transfer rates by an order of magnitude. Replacement of a p-xylene bridge by a p-dimethoxybenzene spacer entails an acceleration of charge transfer rates by a factor of 3.5. In the dyads from this study, the relative order of importance of individual influences on electron transfer rates is therefore as follows: solvent polarity ≥ driving-force > donor–bridge energy gap.

  四个由Ru（bpy）3 2+（py = 2,2'-联吡啶）合成了光敏剂，9,10-蒽醌电子受体和连接两个氧化还原伙伴的分子桥，并通过光谱学和电化学方法进行了研究。试图评估驱动力，溶剂极性和桥变异对这些分子中光诱导电子转移速率的相对重要性。预期地，在钌络合物的联吡啶配体中引入叔丁基取代基，并改变溶剂二氯甲烷 到 乙腈导致电荷传输速率的显着加速。在二氯甲烷因此，光诱导的电子转移与光敏剂固有的激发态失活过程没有竞争性。在乙腈通过将叔丁基取代基连接到bpy辅助配体上，驱动力增加了0.2 eV，导致电子传递速率增加了一个数量级。用对二甲氧基苯间隔基代替对二甲苯桥，使电荷转移速率加速了3.5倍。因此，在这项研究的二元组中，各个因素对电子传输速率的重要性的相对顺序如下：溶剂极性≥驱动力>供体-桥能隙。
• Photoinduced Electron Transfer in Linear Triarylamine–Photosensitizer–Anthraquinone Triads with Ruthenium(II), Osmium(II), and Iridium(III)
  作者：Jihane Hankache、Marja Niemi、Helge Lemmetyinen、Oliver S. Wenger

  DOI：10.1021/ic300558s

  日期：2012.6.4

  A rigid rod-like organic molecular ensemble comprised of a triarylamine electron donor, a 2,2'-bipyridine (bpy) ligand, and a 9,10-anthraquinone acceptor was synthesized and reacted with suitable metal precursors to yield triads with Ru(bpy)(3)(2+), Os(bpy)(3)(2+), and [Ir(2-(p-tolyl)pyridine)(2)(bpy)](+) photosensitizers. Photoexcitation of these triads leads to long-lived charge-separated states (tau = 80-1300 ns) containing a triarylamine cation and an anthraquinone anion, as observed by transient absorption spectroscopy. From a combined electrochemical and optical spectroscopic study, the thermodynamics and kinetics for the individual photoinduced charge-separation and thermal charge-recombination events were determined; in some cases, measurements on suitable donor-sensitizer or sensitizer-acceptor dyads were necessary. In the case of the ruthenium and iridium triads, the fully charge-separated state is formed in nearly quantitative yield.
• Photoinduced Electron Transfer in Rhenium(I)–Oligotriarylamine Molecules
  作者：Annabell G. Bonn、Markus Neuburger、Oliver S. Wenger

  DOI：10.1021/ic501620g

  日期：2014.10.20

  Two molecular triads with an oligotriarylamine multielectron donor were synthesized and investigated with a view to obtaining charge-separated states in which the oligotriarylamine is oxidized 2-fold. Such photoinduced accumulation of multiple redox equivalents is of interest for artificial photosynthesis. The first triad was comprised of the oligotriarylamine and two rhenium(I) tricarbonyl diimine photosensitizers each of which can potentially accept one electron. In the second triad the oligotriarylamine was connected to anthraquinone, in principle an acceptor of two electrons, via a rhenium(I) tricarbonyl diimine unit. With nanosecond transient absorption spectroscopy (using an ordinary pump-probe technique) no evidence for the generation of 2-fold oxidized oligotriarylamine or 2-fold reduced anthraquinone was found. The key factors limiting the photochemistry of the new triads to simple charge separation of one electron and one hole are discussed, and the insights gained from this study are useful for further research in the area of charge accumulation in purely molecular (nanoparticle-free) systems. An important problem of the rhenium-based systems considered here is the short wavelength required for photoexcitation. In the second triad, photogenerated anthraquinone monoanion is protonated by organic acids, and the resulting semiquinone species leads to an increase in lifetime of the charge-separated state by about an order of magnitude. This shows that the proton-coupled electron transfer chemistry of quinones could be beneficial for photoinduced charge accumulation.