N,N'-bis(4-ethoxyphenyl)phenylamine | 106614-62-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis(4-ethoxyphenyl)phenylamine
• 英文别名: 4-Ethoxy-N-(4-ethoxyphenyl)-N-phenylaniline
• CAS: 106614-62-4
• 化学式: C₂₂H₂₃NO₂
• 分子量: 333.43
• InChiKey: UROIRNLDLUGGKP-UHFFFAOYSA-N

物化性质

• 沸点：
  476.6±30.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-bis(4-ethoxyphenyl)phenylamine 在 potassium iodide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 bis(4-ethoxyphenyl)[4-(5-nitro-1H-benzoimidazol-2-yl)phenyl]amine
  参考文献：
  名称：

  Aggregation-induced and crystallization-enhanced emissions with time-dependence of a new Schiff-base family based on benzimidazole

  摘要：

  已经通过缩合反应合成了一种新的含有[4-(1H-苯并咪唑-2-基)-苯基]-双-(4-乙氧基苯基)-胺的席夫碱家族。

  DOI：

  10.1039/c3tc32551b
• 作为产物：
  描述：

  4-碘苯酚 在 cesium hydroxide 、 18-冠醚-6 、 铜 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 91.0h， 生成 N,N'-bis(4-ethoxyphenyl)phenylamine
  参考文献：
  名称：

  Aggregation-induced and crystallization-enhanced emissions with time-dependence of a new Schiff-base family based on benzimidazole

  摘要：

  已经通过缩合反应合成了一种新的含有[4-(1H-苯并咪唑-2-基)-苯基]-双-(4-乙氧基苯基)-胺的席夫碱家族。

  DOI：

  10.1039/c3tc32551b

文献信息

• A series of triphenylamine-based two-photon absorbing materials with AIE property for biological imaging
  作者：Yanqiu Liu、Ming Kong、Qiong Zhang、Zhiwen Zhang、Hongping Zhou、Shengyi Zhang、Shengli Li、Jieying Wu、Yupeng Tian

  DOI：10.1039/c4tb00464g

  日期：——

  One- and two-photon fluorescence properties of six chromophores were successfully tuned by a simple structure modification. The chromophore3Bwith significant AIE and 2PA effect shows promise in bioimaging applications.

  通过简单的结构修改，成功调控了六种色素的一光子和双光子荧光特性。具有显著AIE（聚集诱导发光）和2PA（双光子吸收）效应的色素3B在生物成像应用中显示出前景。

• D–A–D type chromophores with aggregation-induced emission and two-photon absorption: synthesis, optical characteristics and cell imaging
  作者：Ai-Xiang Ding、Hu-Jun Hao、Yong-Guang Gao、You-Di Shi、Quan Tang、Zhong-Lin Lu

  DOI：10.1039/c6tc00781c

  日期：——

  Substituent tuned D–A–D type chromophores with good AIE and TPA properties were successfully applied as OPEF and TPEF cellular stains.

  取代基调制的D-A-D型色团具有良好的AIE和TPA性质，成功地应用于OPEF和TPEF细胞染料。
• Synthesis, crystal structures, and two-photon absorption of a series of cyanoacetic acid triphenylamine derivatives
  作者：Fuying Hao、Dandan Li、Qiong Zhang、Shengli Li、Shengyi Zhang、Hongping Zhou、Jieying Wu、Yupeng Tian

  DOI：10.1016/j.saa.2015.06.030

  日期：2015.11

  A specific series of chromophores (CN1, CN2, CN3, and CN4) have been synthesized, in which contained a triphenylamine moiety as the electron donor (D), a cyanoacetic acid moiety as the electron acceptor (A), vinylene or phenylethyne as the pi-bridge, and ethyoxyl groups as auxiliary electron donor (D') to construct the D-pi-A or D'-D-pi-A molecular configuration. Photophysical properties of them were systematically investigated. These results show that the chromophores display a solvatochromism (blue shift) and large Stokes shifts for their absorption bands with increasing polarity of the solvent. Furthermore, the chromophore CN4 shows the strongest intensity of two-photon excited fluorescence and largest two-photon absorption cross section (2783 GM) in the near infrared region. Finally, the connections between the structures and properties are systematically investigated relying on the information from linear and nonlinear optical properties, crytsal structures and quantum chemical calculation. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis, crystals of centrosymmetric triphenylamine chromophores bearing prodigious two-photon absorption cross-section and biological imaging
  作者：Shichao Wang、Shasha Xu、Yiming Wang、Xiaohe Tian、Yujin Zhang、Chuankui Wang、Jieying Wu、Jiaxiang Yang、Yupeng Tian

  DOI：10.1016/j.saa.2016.10.059

  日期：2017.2

  Two centrosymmetric D-pi-D type triphenylamine chromophores with long pi-conjugated bridge and strong electron-donating moiety were designed, synthesized and fully characterized. The crystal analysis revealed that multiple C-H center dot center dot center dot pi interactions existed in two chromophores, which played a crucial role in generating molecular 1D chains and 2D layers structures. Linear and nonlinear optical properties of the chromophores were systematically investigated with the aid of theoretical calculations. Two chromophores both exhibited intense and wide-dispersed one-photon/two-photon excited fluorescence, bear prodigious 2PA cross section (delta). Especially for Dye2, with ethyoxyl groups, displayed the strong 2PA activity, large cross-sections (delta(max) > 16,000 GM) and high NLO efficiency (delta(max)/MW > 16 GM/(g.mol)) in the range of 680-830 nm in DMF. In addition, one- and two-photon fluorescence microscopy images of HepG2 cells incubated with Dye2 were obtained and found that Dye2 could effectively uptake toward living cells and display a uniformly localized in cytosolic space. (C) 2016 Elsevier B.V. All rights reserved.