N-(9-anthrylmethyl)diethanolamine | 109297-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(9-anthrylmethyl)diethanolamine
• 英文别名: N,N-bis(2-hydroxyethyl)-9-anthracenemethanamine；Ethanol, 2,2'-[(9-anthracenylmethyl)imino]bis-；2-[anthracen-9-ylmethyl(2-hydroxyethyl)amino]ethanol
• CAS: 109297-66-7
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: LEBZMXYJDNWXPS-UHFFFAOYSA-N

物化性质

• 沸点：
  526.9±30.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(9-anthrylmethyl)diethanolamine 在 氯化亚砜 作用下， 以65%的产率得到N-(anthracen-9-ylmethyl)-2-chloro-N-(2-chloroethyl)ethanamine
  参考文献：
  名称：

  A simple and robust PET-based anthracene-appended O-N-O chelate for sequential recognition of Fe3+/CN– ions in aqueous media and its multimodal applications

  摘要：

  A very simple, robust, and pico/nanomolar-sensitive 9,10-diethanolamine-substituted fluorescent Fe3+/CN- probe (PD) was synthesised, and its sensing abilities towards various ions were studied in mixed aqueous media. PD selectively recognised Fe3+ ions through a 'turn on' response with an excellent binding constant (K-a, 9.29x10(6)M(-1)) in 1:2 binding stoichiometry at pH 7.0 in phosphate-buffered saline (PBS). The in situ generated Fe3+center dot PD ensemble sequentially recognised CN- ions with an excellent binding constant (K-a 1.72x10(8)M(-1)) via a 'turn off' mode by extruding Fe3+ ions from the ensemble. The highly selective sequential 'on-off' responses towards Fe3+ and CN- ions were attributed to inhibition and restoration of photoinduced electron transfer (PET) and chelation-induced enhanced fluorescence (CHEF) effects from the chelating N and O heteroatoms. PD was able to detect Fe3+ and CN- ions in real water samples satisfactorily at picomolar to sub-nanomolar levels. A colorimetric assay based on pyrocatechol violet (PCV) was also able to detect Fe3+/CN- in a sequential manner (up to sub-micromolar level) by a change in colour from colourless to yellow/pale green without any interferences from other ions. Based on the complexation and decomplexation mechanism, bio-imaging photonic INHIBIT logic circuit strips were prepared for use under physiological conditions. In addition, solid-phase recognition of Fe3+/CN- ions was demonstrated using cost-effective paper-based strips.

  DOI：

  10.1016/j.ica.2018.07.007
• 作为产物：
  描述：

  9-蒽甲醛 在 sodium tetrahydroborate 、 三溴化磷 、 potassium carbonate 、 potassium hydrogencarbonate 、 potassium iodide 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 N-(9-anthrylmethyl)diethanolamine
  参考文献：
  名称：

  A simple and robust PET-based anthracene-appended O-N-O chelate for sequential recognition of Fe3+/CN– ions in aqueous media and its multimodal applications

  摘要：

  A very simple, robust, and pico/nanomolar-sensitive 9,10-diethanolamine-substituted fluorescent Fe3+/CN- probe (PD) was synthesised, and its sensing abilities towards various ions were studied in mixed aqueous media. PD selectively recognised Fe3+ ions through a 'turn on' response with an excellent binding constant (K-a, 9.29x10(6)M(-1)) in 1:2 binding stoichiometry at pH 7.0 in phosphate-buffered saline (PBS). The in situ generated Fe3+center dot PD ensemble sequentially recognised CN- ions with an excellent binding constant (K-a 1.72x10(8)M(-1)) via a 'turn off' mode by extruding Fe3+ ions from the ensemble. The highly selective sequential 'on-off' responses towards Fe3+ and CN- ions were attributed to inhibition and restoration of photoinduced electron transfer (PET) and chelation-induced enhanced fluorescence (CHEF) effects from the chelating N and O heteroatoms. PD was able to detect Fe3+ and CN- ions in real water samples satisfactorily at picomolar to sub-nanomolar levels. A colorimetric assay based on pyrocatechol violet (PCV) was also able to detect Fe3+/CN- in a sequential manner (up to sub-micromolar level) by a change in colour from colourless to yellow/pale green without any interferences from other ions. Based on the complexation and decomplexation mechanism, bio-imaging photonic INHIBIT logic circuit strips were prepared for use under physiological conditions. In addition, solid-phase recognition of Fe3+/CN- ions was demonstrated using cost-effective paper-based strips.

  DOI：

  10.1016/j.ica.2018.07.007

文献信息

• The first fluorescent sensor for boronic and boric acids with sensitivity at sub-micromolar concentrations
  作者：Wei Wang、Greg Springsteen、Shouhai Gao、Binghe Wang

  DOI：10.1039/b002089n

  日期：——

  An anthracene-based PET sensor which uses a diethanolamine recognition site is selective for boronic and boric acids, showing up to a 19-fold fluorescent intensity enhancement upon binding.

  一种基于蒽的 PET 传感器使用二乙醇胺识别位点，对硼酸和硼酸具有选择性，结合后荧光强度最多可增强 19 倍。
• A Facile Strategy To Construct PDLLA-PTMEG Network with Triple-Shape Effect via Photo-Cross-Linking of Anthracene Groups
  作者：Hui Xie、Chuan-Ying Cheng、Lan Du、Cheng-Jie Fan、Xiao-Ying Deng、Ke-Ke Yang、Yu-Zhong Wang

  DOI：10.1021/acs.macromol.6b00382

  日期：2016.5.24

  Covalently cross-linked network has been widely applied in triple-shape memory polymers (TSPs), and fabricating triple-shape memory networks with the optional shapes through a facile and fast way is highly expected in the real applications. In this study, a “preshaped and post-cross-linking” strategy has been put forward to fabricate the triple-shape networks via fast photo-cross-linking in solid state

  共价交联网络已广泛应用于三重形状记忆聚合物（TSP）中，并且在实际应用中，人们高度希望通过便捷的方法制造具有任意形状的三重形状记忆网络。在这项研究中，提出了一种“预成形和后交联”的策略，以通过固态快速光交联来制造三重形状的网络。首先使用光响应性蒽基开发聚（d，l-丙交酯）–聚（四亚甲基氧化）二醇（PDLLA-PTMEG）网络通过紫外线照射。网络制造涉及两个步骤：首先，合成在侧链上含有蒽基的线性共聚物（AN-PDLLA-PTMEG），其中PDLLA链段的质量比不同，然后合成PDLLA-PTMEG网络（NW-PDLLA-PTMEG）。在氩气氛下通过365nm UV光照射形成的。所有前体的结构由1确定1 H NMR和所有网络均通过溶胀测试进行评估。拉伸试验的结果表明，PDLLA链段的含量对材料的机械性能具有至关重要的影响。差示扫描量热法（DSC）分析与动态力学分析（DMA）结合显示，所有NW-P
• Selective Decrosslinking in Liquid Crystal Polymer Actuators for Optical Reconfiguration of Origami and Light‐Fueled Locomotion
  作者：Zhi‐Chao Jiang、Yao‐Yu Xiao、Xia Tong、Yue Zhao

  DOI：10.1002/anie.201900470

  日期：2019.4.8

  The ability to optically reconfigure an existing actuator of a liquid crystal polymer network (LCN) so that it can display a new actuation behavior or function is highly desired in developing materials for soft robotics applications. Demonstrated here is a powerful approach relying on selective polymer chain decrosslinking in a LCN actuator with uniaxial LC alignment. Using an anthracene‐containing

  在开发用于软机器人技术的材料时，高度需要光学重新配置液晶聚合物网络（LCN）的现有执行器的功能，使其能够显示新的执行行为或功能。这里展示了一种强大的方法，该方法依赖于具有单轴LC排列的LCN驱动器中的选择性聚合物链解交联。使用含蒽的LCN，可以通过在254 nm紫外光下对蒽二聚体进行光裂解来实现空间控制的光学去交联，从而改变驱动（交联）和非驱动（去交联）域的分布，从而根据顺序确定驱动行为混乱的相变。基于这种机制，可以按需重新配置具有扁平形状的单个执行器，以显示可逆的形状转换，例如自动折叠成折纸三维结构。此外，通过使用染料掺杂的LCN执行器，可以对光载微行人进行光学配置，使其具有不同的运动行为，从沿激光扫描方向移动到沿相反方向移动。
• Detection of hydrogen peroxide using dioxazaborocanes: elucidation of the sensing mechanism at the molecular level by NMR and XPS measurements
  作者：Thomas Caron、Pascal Palmas、Céline Frénois、Christophe Méthivier、Eric Pasquinet、Claire-Marie Pradier、Françoise Serein-Spirau、Lionel Hairault、Pierre Montméat

  DOI：10.1039/d0nj00038h

  日期：——

  A fluorescent dioxazaborocane was synthesised and characterized, in order to study its turn-off sensing process for hydrogen peroxide detection. The exposure of the dioxazaborocane to diluted vapours of H2O2 led to a strong non reversible quenching of the fluorescence. Both NMR and XPS analyses were carried out before and after exposure of dioxazaborocane to H2O2 vapours. They unequivocally show that

  合成并表征了一种荧光二恶唑硼烷，以研究其关断感应过程以检测过氧化氢。二恶唑烷硼烷暴露于H 2 O 2稀释蒸气中会导致强烈的不可逆荧光猝灭。NMR和XPS分析均在二恶唑硼烷暴露于H 2 O 2蒸气之前和之后进行。他们明确表明，薄膜中的硼原子被N-B键断裂而被氧化。一致的XPS数据支持通过NMR鉴定产物（例如苯酚和硼酸），从而使整个反应顺序得以解释，从而说明了二氧杂硼烷在H 2 O 2上的荧光猝灭。曝光要准确描述。仅少量观察到二氧杂硼硼烷直接水解为二醇，而没有氧化。
• Photoactive chemosensors 3 : a unique case of fluorescence enhancement with Cu(<scp>ii</scp>)
  作者：Sukhdeep Kaur、Subodh Kumar

  DOI：10.1039/b209053h

  日期：——

  Chemosensor (4a) shows fluorescence enhancement with Cu(II) and can estimate 1–300 μM Cu(II) by using fluorescence (1–20 μM) and UV–Vis (10–300 μM) spectroscopic techniques. Ni(II), Cd(II), Zn(II), Ag(I) and Hg(II) do not interfere in fluorescence studies and only Ag(I) and Hg(II) interfere in UV–Vis studies.

  化学传感器（4a）在使用 Cu（II）时荧光增强，利用荧光（1-20 μM）和紫外可见光（10-300 μM）光谱技术可估算出 1-300 μM 的 Cu（II）。镍（II）、镉（II）、锌（II）、银（I）和汞（II）不干扰荧光研究，只有银（I）和汞（II）干扰紫外可见光研究。