N-methyl-N-[2-[2-[2-(N-methylanilino)ethoxy]ethoxy]ethyl]aniline | 126739-49-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-N-[2-[2-[2-(N-methylanilino)ethoxy]ethoxy]ethyl]aniline
• CAS: 126739-49-9
• 化学式: C₂₀H₂₈N₂O₂
• 分子量: 328.455
• InChiKey: WBJDZMORKZITDI-UHFFFAOYSA-N

物化性质

• 沸点：
  460.3±35.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-N-[2-[2-[2-(N-methylanilino)ethoxy]ethoxy]ethyl]aniline 在 哌啶 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 73.0h， 生成
  参考文献：
  名称：

  Conformational Switching and Exciton Interactions in Hemicyanine-Based Bichromophores

  摘要：

  Conformational changes in two hemicyanine-based bichromophores were demonstrated by varying the polarity as well as temperature of the medium. Dramatic changes in the ground and excited singlet state properties were observed upon folding of the bichromophores, due to the formation of intramolecular aggregates of H-type. These aspects were studied, in detail, using steady-state absorption and time-resolved fluorescence spectroscopy. Time-resolved fluorescence studies indicate that both the bichromophores exhibit a monoexponential decay, with a short lifetime, in mixed toluene-CH2Cl2 solvents having lower proportions of toluene. Interestingly, biexponential decay with short and long-lived species was observed at higher proportions of toluene, due to the presence of unfolded and folded forms. Folding results in the intramolecular stacking of the chromophores which restrict their torsional dynamics, leading to a longer lifetime. Upon laser excitation, the folded form of the bichromophore undergoes rapid conformational changes, due to photoinduced thermal dissociation.

  DOI：

  10.1021/ja010199v
• 作为产物：
  描述：

  1,2-双甲苯氧基乙烷 、 N-甲基-N-羟乙基苯胺 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以45%的产率得到N-methyl-N-[2-[2-[2-(N-methylanilino)ethoxy]ethoxy]ethyl]aniline
  参考文献：
  名称：

  A Controlled Supramolecular Approach toward Cation-Specific Chemosensors:  Alkaline Earth Metal Ion-Driven Exciton Signaling in Squaraine Tethered Podands

  摘要：

  Three different squaraine tethered bichromophoric podands 3a-c with one, two, and three oxygen atoms in the podand chain and an analogous monochromophore 4a were synthesized and characterized. Among these, the bichromophores 3a-c showed high selectivity toward alkaline earth metal cations, particularly to Mg2+ and Ca2+ ions, whereas they were optically silent toward alkali metal ions. From the absorption and emission changes as well as from the Job plots, it is established that Mg2+ ions form 1:1 folded complexes with 3a and 3b whereas Ca2+ ions prefer to form 1:2 sandwich dimers. However, 3c invariably forms weak 1:1 complexes with Mg2+, Ca2+, and Sr2+ ions. The signal output in all of these cases was achieved by the formation of a sharp blue-shifted absorption and strong quenching of the emission of 3a-c. The signal transduction is achieved by the exciton interaction of the face-to-face stacked squaraine chromophores of the cation complex, which is a novel approach of specific cation sensing. The observed cation-induced changes in the optical properties are analogous to those of the "H" aggregates of squaraine dyes. Interestingly, a monochromophore 4a despite its binding, as evident from H-1 NMR studies, remained optically silent toward Mg2+ and Ca2+ ions. While the behavior of 4a toward Mg2+ ion is understood, its optical silence toward Ca2+ ion is rationalized to the preferential formation of a "Head-Tail-Tail-Head" arrangement in which exciton coupling is not possible. The present study is different from other known reports on chemosensors in the sense that cation-specific supramolecular host-guest complexation has been exploited for controlling chromophore interaction via cation-steered exciton coupling as the mode of signaling.

  DOI：

  10.1021/ja0393776

文献信息

• A Controlled Supramolecular Approach toward Cation-Specific Chemosensors:  Alkaline Earth Metal Ion-Driven Exciton Signaling in Squaraine Tethered Podands
  作者：Easwaran Arunkumar、Parayali Chithra、Ayyappanpillai Ajayaghosh

  DOI：10.1021/ja0393776

  日期：2004.6.1

  Three different squaraine tethered bichromophoric podands 3a-c with one, two, and three oxygen atoms in the podand chain and an analogous monochromophore 4a were synthesized and characterized. Among these, the bichromophores 3a-c showed high selectivity toward alkaline earth metal cations, particularly to Mg2+ and Ca2+ ions, whereas they were optically silent toward alkali metal ions. From the absorption and emission changes as well as from the Job plots, it is established that Mg2+ ions form 1:1 folded complexes with 3a and 3b whereas Ca2+ ions prefer to form 1:2 sandwich dimers. However, 3c invariably forms weak 1:1 complexes with Mg2+, Ca2+, and Sr2+ ions. The signal output in all of these cases was achieved by the formation of a sharp blue-shifted absorption and strong quenching of the emission of 3a-c. The signal transduction is achieved by the exciton interaction of the face-to-face stacked squaraine chromophores of the cation complex, which is a novel approach of specific cation sensing. The observed cation-induced changes in the optical properties are analogous to those of the "H" aggregates of squaraine dyes. Interestingly, a monochromophore 4a despite its binding, as evident from H-1 NMR studies, remained optically silent toward Mg2+ and Ca2+ ions. While the behavior of 4a toward Mg2+ ion is understood, its optical silence toward Ca2+ ion is rationalized to the preferential formation of a "Head-Tail-Tail-Head" arrangement in which exciton coupling is not possible. The present study is different from other known reports on chemosensors in the sense that cation-specific supramolecular host-guest complexation has been exploited for controlling chromophore interaction via cation-steered exciton coupling as the mode of signaling.
• Conformational Switching and Exciton Interactions in Hemicyanine-Based Bichromophores
  作者：S. Zeena、K. George Thomas

  DOI：10.1021/ja010199v

  日期：2001.8.1

  Conformational changes in two hemicyanine-based bichromophores were demonstrated by varying the polarity as well as temperature of the medium. Dramatic changes in the ground and excited singlet state properties were observed upon folding of the bichromophores, due to the formation of intramolecular aggregates of H-type. These aspects were studied, in detail, using steady-state absorption and time-resolved fluorescence spectroscopy. Time-resolved fluorescence studies indicate that both the bichromophores exhibit a monoexponential decay, with a short lifetime, in mixed toluene-CH2Cl2 solvents having lower proportions of toluene. Interestingly, biexponential decay with short and long-lived species was observed at higher proportions of toluene, due to the presence of unfolded and folded forms. Folding results in the intramolecular stacking of the chromophores which restrict their torsional dynamics, leading to a longer lifetime. Upon laser excitation, the folded form of the bichromophore undergoes rapid conformational changes, due to photoinduced thermal dissociation.