4-(2-(4-aminophenyl)ethenyl)-N,N-diphenylaniline | 160714-44-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(2-(4-aminophenyl)ethenyl)-N,N-diphenylaniline
• 英文别名: 4-(4‐aminophenylethenyl)‐N,N‐diphenylaniline；4-[2-[4-(N-phenylanilino)phenyl]ethenyl]aniline
• CAS: 160714-44-3
• 化学式: C₂₆H₂₂N₂
• 分子量: 362.474
• InChiKey: IQMLNPPTMVJUJD-UHFFFAOYSA-N

物化性质

• 沸点：
  565.2±39.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吡啶-2-甲醛 、 4-(2-(4-aminophenyl)ethenyl)-N,N-diphenylaniline 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以88.4%的产率得到
  参考文献：
  名称：

  一种可检测活细胞线粒体中镍离子的高选择 性荧光探针及其制备方法

  摘要：

  一种可检测活细胞线粒体中镍离子的高选择性荧光探针及其制备方法，该探针为含吡啶基三苯胺基胺类衍生物，制备方法中，以三苯胺为起始原料，先制备中间体Ⅰ4‑(N,N‑二苯基氨基)苯甲醛和中间体Ⅱ对硝基甲苯的膦盐，然后由中间体1和Ⅱ制备4‑对硝基苯乙烯基三苯胺中间体，进而在Pd/C，水合肼作用下还原得到的4‑对氨基苯乙烯基三苯胺，接着与2‑吡啶苯甲醛通过缩合反应得到席夫碱，席夫碱在硼氢化钠的作用下还原得目标产物。本发明探针在425nm左右具有良好的单光子荧光性质。HepG2细胞被目标产物染色后，可清晰地观察到有机材料对HepG2细胞细胞质中的线粒体具有高的成像能力，并能可逆地检测线粒体中的镍离子。本发明探针对于有机染料的设计、制备和生命科学研究具有重大的意义。

  公开号：

  CN105670608B
• 作为产物：
  描述：

  4-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 palladium on activated charcoal 、 potassium tert-butylate 、 一水合肼 、 过氧化苯甲酰 作用下， 反应 11.0h， 生成 4-(2-(4-aminophenyl)ethenyl)-N,N-diphenylaniline
  参考文献：
  名称：

  A series of triphenylamine-based two-photon absorbing materials with AIE property for biological imaging

  摘要：

  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。

  DOI：

  10.1039/c4tb00464g

文献信息

• Tuning the donors to control the lifetimes of charge-separated states in triazine-based donor-acceptor systems
  作者：Ting Lu、Haiya Sun、Nathan D. Colley、Chelsea N. Bridgmohan、Dongzhi Liu、Wei Li、Wenping Hu、Xueqin Zhou、Tianyang Wang、Lichang Wang

  DOI：10.1016/j.dyepig.2016.08.042

  日期：2017.1

  The back electron transfer processes of these donor-acceptor systems occur in the inverted region of the Marcus curve. The driving forces of back electron transfer and the reorganization energies of electron transfer decrease in the order of 9-phenyl carbazole derivative, 4,4’-di(hydro, methyl, methoxy or octyloxy) triphenylamine derivative and 4-methylphenyl indoline derivative. These two factors

  合成并表征了以苯乙烯基9-苯基咔唑，4,4'-二（氢，甲基，甲氧基或辛氧基）三苯胺和4-甲基苯基二氢吲哚衍生物为供体，以s-三嗪基为受体的六个供体-受体体系。 。这些施主-受主系统的电荷分离状态是通过有效的光诱导电子从激发的施主模块转移到受主模块而产生的，寿命范围为57 ns至215 ns。这些供体-受体系统能够快速分离电荷，但电荷重组非常缓慢。这些供体-受体系统的反向电子转移过程发生在马库斯曲线的反向区域中。反向电子转移的驱动力和电子转移的重组能按9-苯基咔唑衍生物的顺序降低，4,4'-二（氢，甲基，甲氧基或辛氧基）三苯胺衍生物和4-甲基苯基二氢吲哚衍生物。这两个因素共同作用，以确定这些供体-受体系统中电荷分离态的不同寿命。
• A triphenylamine as a fluorophore and maleimide as a bonding group selective turn-on fluorescent imaging probe for thiols
  作者：Tao Liu、Fangjun Huo、Caixia Yin、Jianfang Li、Jianbin Chao、Yongbin Zhang

  DOI：10.1016/j.dyepig.2015.12.031

  日期：2016.5

  With the biological importance of biothiols, the development of probes for thiols has been an active research area in recent years. Here, we report a novel thiol-reactive fluorescent probe based on Michael addition reaction for selectively detecting thiols over other relevant biological species. The thiol adduct was characterized using NMR and mass spectroscopy and detection mechanism was further confirmed

  鉴于生物硫醇的生物学重要性，近年来，硫醇探针的开发一直是活跃的研究领域。在这里，我们报告基于迈克尔加成反应的新型硫醇反应性荧光探针，用于选择性检测其他相关生物物种上的硫醇。使用NMR和质谱对硫醇加合物进行表征，并进一步确定了检测机理。该传感器对生物硫醇的选择性优于其他氨基酸，具有信号响应时间短，线性范围好和检测限低的特点。对于传感器的实际应用，它可以用于通过开启荧光成像来监测活细胞中的硫醇。
• Bridge improvement work: maximising non-linear optical performance in polyoxometalate derivatives
  作者：Claire F. Jones、Bethany R. Hood、Yovan de Coene、Ivan Lopez-Poves、Benoît Champagne、Koen Clays、John Fielden

  DOI：10.1039/d3cc05433k

  日期：——

  New phenyl and stilbene-bridged polyoxometalate (POM) charge-transfer chromophores with diphenylamino donor groups produce, respectively, the highest intrinsic and absolute quadratic hyperpolarisabilities measured for such species.

  带有二苯基氨基供体基团的新型苯基和二苯乙烯桥接聚氧化金属盐（POM）电荷转移发色团分别产生了此类物质中最高的本征和绝对二次超极性。
• 1, 3, 5-Triazine-cored derivatives dyes containing triphenylamine based two-photon absorption: Synthesis, optical characterization and bioimaging
  作者：Hongping Zhou、Zheng Zheng、Guoyi Xu、Zhipeng Yu、Xiaofei Yang、Longhuai Cheng、Xiaohe Tian、Lin Kong、Jieying Wu、Yupeng Tian

  DOI：10.1016/j.dyepig.2012.03.017

  日期：2012.9

  A series of new one, two and three-branched two-photon absorption triazine dyes containing triphenylamine with a pi-bond and a sigma-electron pair as a bridge, and different electron-donating groups, have been synthesized and their photophysical properties have been systematically investigated. These dyes showed obvious solvatochromic effects, i.e., significant bathochromic shifting of the emission spectra and larger Stokes shifts were observed in more polar solvents mainly due to intramolecular charge-transfer (ICT). The two-photon absorption (2PA) cross section values were determined by two-photon excited fluorescence (TPEF) measurements in DMF. This result further proved that a sigma-electron pair as a bridge is an efficient way to transfer charge as well as a pi bridge to provide a large 2PA cross section, and that their 2PA cross section values (delta) increase with increasing electron-donating strength of the end group and branch number. In addition, two-photon fluorescence cell imaging of dye 7a in HeLa and MCF-7 cancer cells was demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.
• New organic conjugated dye nano-aggregates exhibiting naked-eye fluorescence color switching
  作者：Ge Ding、Yao Lu、Xiaozhuan Qin、Jihong Su、Shengtao Zhang、Hongru Li、Ziping Luo、Lingyun Chen、Fang Gao

  DOI：10.1016/j.dyepig.2016.12.021

  日期：2017.4

  In this study, a variety of new conjugated containing strong electron-donating groups were prepared for formation of organic nano-scale aggregates. The properties and aggregation modes of these aggregates were investigated on basis of time dependent absorption, fluorescence emission spectra as well as scanning electron microscope images. The results show that nano organic aggregates could be yielded by the linear dyes in mixed DMF/H2O solvent through a simple re-precipitation method, while no aggregates of the branched dyes were produced. X-ray diffraction of single crystal and X-ray diffraction patterns of the powders results demonstrate that the linear dyes tend to show ordered molecular arrangements, while the armed dyes do not exhibit such a tendency. A remarkable fluorescence switching process under 365 nm lamp was observed for the target aggregates. This study successfully provides real examples of organic aggregates in mixed DMF/H2O solvent which have great capacity to show enhanced fluorescence color switching. (C) 2016 Elsevier Ltd. All rights reserved.