4'-[10-methyl-anthracen-9-yl]-2,2':6',2''-terpyridine | 863481-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4'-[10-methyl-anthracen-9-yl]-2,2':6',2''-terpyridine
• 英文别名: 4'-(10-methyl-9-anthryl)-2,2':6'2''-terpyridine；4-(10-Methylanthracen-9-yl)-2,6-dipyridin-2-ylpyridine；4-(10-methylanthracen-9-yl)-2,6-dipyridin-2-ylpyridine
• CAS: 863481-31-6
• 化学式: C₃₀H₂₁N₃
• 分子量: 423.517
• InChiKey: UVPRZHAHOAFWTG-UHFFFAOYSA-N

物化性质

• 沸点：
  595.6±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-[10-methyl-anthracen-9-yl]-2,2':6',2''-terpyridine 在 氯化亚砜 、 硫酸 、 水 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 84.0h， 生成 dimethyl-4'-(10-methyl-9-anthryl)-2,2':6'2''-terpyridine-6,6''-dicarboxylate
  参考文献：
  名称：

  A Europium(III) Complex as an Efficient Singlet Oxygen Luminescence Probe

  摘要：

  A new europium(III) complex, [4'-(10-methyl-9-anthryl)-2,2': 6', 2"-terpyridine-6,6"-diyl] bis(methylenenitrilo) tetrakis(acetate)-Eu3+, was designed and synthesized as a highly sensitive and selective time-gated luminescence probe for singlet oxygen (O-1(2)). The new probe is highly water soluble with a large stability constant of similar to 10(21) and a wide pH available range (pH 3-10), and can specifically react with O-1(2) to form its endoperoxide (EP-MTTA-Eu3+) with a high reaction rate constant at 10(10) M-1 s(-1), accompanied by the remarkable increases of luminescence quantum yield from 0.90% to 13.8% and lifetime from 0.80 to 1.29 ms, respectively. The wide applicability of the probe was demonstrated by detection of O-1(2) generated from a MoO42-/H2O2 system, a photosensitization system of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)-porphyrin tetra(p-toluenesulfonate) (TMPyP), and a horseradish peroxidase catalyzed aerobic oxidation system of indole-3-acetic acid (IAA). In addition, it was found that the new probe could be easily transferred into living HeLa cells by incubation with TMPyP. A time-gated luminescence imaging technique that can fully eliminate the short-lived background fluorescence from TMPyP and cell components has been successfully developed for monitoring the time-dependent generation of O-1(2) in living cells.

  DOI：

  10.1021/ja062990f
• 作为产物：
  描述：

  10-甲基蒽-9-甲醛 在 氢氧化钾 、 potassium tert-butylate 、 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 28.0h， 生成 4'-[10-methyl-anthracen-9-yl]-2,2':6',2''-terpyridine
  参考文献：
  名称：

  A Europium(III) Complex as an Efficient Singlet Oxygen Luminescence Probe

  摘要：

  A new europium(III) complex, [4'-(10-methyl-9-anthryl)-2,2': 6', 2"-terpyridine-6,6"-diyl] bis(methylenenitrilo) tetrakis(acetate)-Eu3+, was designed and synthesized as a highly sensitive and selective time-gated luminescence probe for singlet oxygen (O-1(2)). The new probe is highly water soluble with a large stability constant of similar to 10(21) and a wide pH available range (pH 3-10), and can specifically react with O-1(2) to form its endoperoxide (EP-MTTA-Eu3+) with a high reaction rate constant at 10(10) M-1 s(-1), accompanied by the remarkable increases of luminescence quantum yield from 0.90% to 13.8% and lifetime from 0.80 to 1.29 ms, respectively. The wide applicability of the probe was demonstrated by detection of O-1(2) generated from a MoO42-/H2O2 system, a photosensitization system of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)-porphyrin tetra(p-toluenesulfonate) (TMPyP), and a horseradish peroxidase catalyzed aerobic oxidation system of indole-3-acetic acid (IAA). In addition, it was found that the new probe could be easily transferred into living HeLa cells by incubation with TMPyP. A time-gated luminescence imaging technique that can fully eliminate the short-lived background fluorescence from TMPyP and cell components has been successfully developed for monitoring the time-dependent generation of O-1(2) in living cells.

  DOI：

  10.1021/ja062990f

文献信息

• Proton-assisted interaction between luminescent species containing diazacrown ethers and anthryl chromophores
  作者：Frédérique Loiseau、Cinzia Di Pietro、Sebastiano Campagna、Marco Cavazzini、Giovanni Marzanni、Silvio Quici

  DOI：10.1039/b500918a

  日期：——

  The multicomponent species 1 and 2 (structural formulas shown in Fig. 1), made of diazacrown receptors and anthracene-based chromophores, have been synthesized, together with 3, an already-known species containing the anthracene chromophore and an appended amino group. The absorption spectra and luminescence properties of 1–3 have been studied in acetonitrile solution, both in the absence and presence of protons. All of the compounds exhibit luminescence, the intensity of which is enhanced in the presence of protons, and have the role of inhibiting the reductive electron transfer emission quenching processes operating in non-protonated 1–3. The emission intensity of an equimolar solution of 1 and 3 is increased by proton addition, as expected, however the maximum of the intensity is reached when acid concentration is about 1.5 times higher than those of 1 or 3. This suggests that proton-assisted interaction between 1 and 3 takes place. The equimolar solution of 2 and 3 exhibits two emission features, each one assigned to a component chromophore. Low acid concentration leads to enhancement of the 400 nm emission, related to the species 3, and higher acid concentration allows for enhancement of the 520 nm emission, related to the species 2. A closer observation of the luminescence titration curve, as well as NMR data, indicates that a 2·3 adduct is present even before proton addition, and the adduct is further stabilized by protonation to form 2·H·3.

  由二氮杂冠受体和基于蒽的发色团组成的多组分物种1和2（结构式如图1所示）以及含有蒽发色团和附加氨基的已知物种3已经合成。 1-3 的吸收光谱和发光性质已经在乙腈溶液中进行了研究，无论是在质子不存在还是存在的情况下。所有化合物均表现出发光，其强度在质子存在下增强，并具有抑制非质子化 1-3 中还原电子转移发射猝灭过程的作用。正如预期的那样，1 和 3 的等摩尔溶液的发射强度通过添加质子而增加，但是当酸浓度比 1 或 3 的溶液高约 1.5 倍时，强度达到最大值。这表明质子辅助相互作用1 和 3 之间发生。 2 和 3 的等摩尔溶液表现出两种发射特征，每一种都分配给一种组分发色团。低酸浓度导致与物种 3 相关的 400 nm 发射增强，而较高的酸浓度则导致与物种 2 相关的 520 nm 发射增强。 更仔细地观察发光滴定曲线以及 NMR数据表明，甚至在质子添加之前就存在2·3加合物，并且该加合物通过质子化进一步稳定以形成2·H·3。
• Light-Emitting Device, Light-Emitting Apparatus, Electronic Device, and Lighting Device
  申请人：Semiconductor Energy Laboratory Co., Ltd.

  公开号：US20200388779A1

  公开（公告）日：2020-12-10

  A light-emitting device with low driving voltage and favorable reliability is provided. The light-emitting device includes an electron-injection layer between a cathode and a light-emitting layer. The electron-injection layer is a mixed film of a metal and an organic compound having a function of interacting with the metal as a tridentate or tetradentate ligand, and the metal atom and the organic compound form SOMO.
• A Europium(III) Complex as an Efficient Singlet Oxygen Luminescence Probe
  作者：Bo Song、Guilan Wang、Mingqian Tan、Jingli Yuan

  DOI：10.1021/ja062990f

  日期：2006.10.1

  A new europium(III) complex, [4'-(10-methyl-9-anthryl)-2,2': 6', 2"-terpyridine-6,6"-diyl] bis(methylenenitrilo) tetrakis(acetate)-Eu3+, was designed and synthesized as a highly sensitive and selective time-gated luminescence probe for singlet oxygen (O-1(2)). The new probe is highly water soluble with a large stability constant of similar to 10(21) and a wide pH available range (pH 3-10), and can specifically react with O-1(2) to form its endoperoxide (EP-MTTA-Eu3+) with a high reaction rate constant at 10(10) M-1 s(-1), accompanied by the remarkable increases of luminescence quantum yield from 0.90% to 13.8% and lifetime from 0.80 to 1.29 ms, respectively. The wide applicability of the probe was demonstrated by detection of O-1(2) generated from a MoO42-/H2O2 system, a photosensitization system of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)-porphyrin tetra(p-toluenesulfonate) (TMPyP), and a horseradish peroxidase catalyzed aerobic oxidation system of indole-3-acetic acid (IAA). In addition, it was found that the new probe could be easily transferred into living HeLa cells by incubation with TMPyP. A time-gated luminescence imaging technique that can fully eliminate the short-lived background fluorescence from TMPyP and cell components has been successfully developed for monitoring the time-dependent generation of O-1(2) in living cells.