4-(N-ethyl-N-(2-hydroxyethyl)amino)benzaldehyde | 63619-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(N-ethyl-N-(2-hydroxyethyl)amino)benzaldehyde
• 英文别名: 4-(ethyl(2-hydroxyethyl)amino)benzaldehyde；4-(N-hydroxyethyl-N-ethyl amino)benzaldehyde；4-[Ethyl(2-hydroxyethyl)amino]benzaldehyde
• CAS: 63619-28-3
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: YOMFQNMFVOQTCI-UHFFFAOYSA-N

物化性质

• 熔点：
  45-47℃
• 沸点：
  364.8±27.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(N-ethyl-N-(2-hydroxyethyl)amino)benzaldehyde 在 盐酸 、 4-甲基苯磺酸吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 61.0h， 生成 4,4'-bis[p-(N-ethyl-N-2-hydroxyethyl)aminostyryl]-2,2'-bipyridine
  参考文献：
  名称：

  新型单和二羟基官能化4,4'-二烯基-2,2'-联吡啶的合成与配位研究

  摘要：

  据报道，方便和大规模制备新的单和双羟基取代的4,4'-双（二烷基氨基苯乙烯基）-2,2'-联吡啶。还描述了他们对[Ru（DEAS-bpy）2 ] 2+（DEAS-bpy = 4,4'-双（二乙基氨基苯乙烯基）-2,2'-联吡啶的配位研究。

  DOI：

  10.1016/s0040-4039(98)01499-3
• 作为产物：
  描述：

  N-乙基-N-羟乙基苯胺 在 sodium hydroxide 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 9.0h， 生成 4-(N-ethyl-N-(2-hydroxyethyl)amino)benzaldehyde
  参考文献：
  名称：

  推挽多烯的便捷合成，旨在制备高效的非线性光学材料

  摘要：

  我们提出了一种方便且通用的合成方法，用于合成带有羟基官能团的推拉式苯基多烯和二苯基多烯。这些发色团由于其大的光学非线性，近红外的透明性以及它们掺入聚合物材料的能力，对于设计高效的非线性光学材料特别感兴趣。

  DOI：

  10.1016/s0040-4039(99)01443-4

文献信息

• Synthesis, Spectroscopy and Photochemistry of Novel Branched Fluorescent Nitro-Stilbene Derivatives with Benzopheonone Groups
  作者：Fang Gao、Jian Liu、Huayong Peng、Nvdan Hu、Hongru Li、Shengtao Zhang

  DOI：10.1007/s10895-010-0611-7

  日期：2010.5

  In this article, we presented novel nitro-stilbene derivatives with one or two benzophenone groups as photoinitiators via multi-steps synthesis. The ultraviolet/visible spectroscopy and the emission spectroscopy of the compounds were determined in various solvents. The results showed that the ultraviolet/visible absorption spectroscopy of the derivatives with benzophenone moiety displayed overlap effects

  在本文中，我们通过多步合成提出了具有一个或两个二苯甲酮基团作为光引发剂的新型硝基二苯乙烯衍生物。在各种溶剂中测定了化合物的紫外/可见光谱和发射光谱。结果表明，具有二苯甲酮部分的衍生物的紫外/可见吸收光谱显示出硝基二苯乙烯和二苯甲酮部分的重叠效应。在非极性溶剂中，衍生物表现出强发射，而在中等和强极性溶剂中表现出弱发射。染料连接的二苯甲酮基团比简单的发色团母体分子显示出更强的荧光发射。广泛研究了衍生物的可见光光引发效应。-5 摩尔/升。而衍生物引发的苯乙烯光聚合效率低于甲基丙烯酸甲酯。我们的结果表明，与染料和光引发剂的简单混合物相比，染料连接的光引发剂具有更有效的光引发作用。此外，具有两个二苯甲酮基团的衍生物比具有一个二苯甲酮基团的衍生物表现出更优异的光钛化效果。评估了导致可见光光诱导分子内电子从生色团部分转移到二苯甲酮部分的热力学驱动。通过核磁共振光谱证实了光反应中产生的苯频哪醇部分。分析了衍生物的热稳定性。
• Facile structure and property tuning through alteration of ring structures in conformationally locked phenyltetraene nonlinear optical chromophores
  作者：Xing-Hua Zhou、Joshua Davies、Su Huang、Jingdong Luo、Zhengwei Shi、Brent Polishak、Yen-Ju Cheng、Tae-Dong Kim、Lewis Johnson、Alex Jen

  DOI：10.1039/c0jm02855j

  日期：——

  A series of phenyltetraene-based nonlinear optical (NLO) chromophores 1a–c with the same donor and acceptor groups, but different tetraene bridges that are partly connected by various sizes of aliphatic rings, have been synthesized and systematically investigated. The interposed conjugated tetraene segments in three chromophores studied are based on isophorone, (1S)-(−)-verbenone, and 3,4,4-trimethyl-2-cyclopentenone, respectively. This kind of structural alteration has significant effect on the intrinsic electronic structures and physical properties of these highly polarizable chromophores as revealed by a variety of characterization techniques. The introduction of the verbenone- and trimethylcyclopentenone-based tetraene bridges could significantly improve the glass-forming ability of chromophores 1b and 1c in comparison with the highly crystalline characteristics of isophorone-based chromophores 1a. More importantly, chromophores 1a–c exhibited distinct optical features in absorption band shape, solvatochromic behavior, as well as energy band gap from the UV-vis-NIR absorption measurements. Quantum mechanical calculations using density functional theory (DFT) were also used to evaluate second-order NLO properties of these chromophores. The electro-optic (EO) coefficients of 1a–c in poled polymers with the 10 wt% chromophore content showed an apparent decrease from 78 pm V−1 for 1a to 42 pm V−1 for 1c. This decrease is attributed to the gradual decrease of the molecular hyperpolarizability (β) of the chromophores which is associated with the progressive cyanine-like electronic structure from the isophorone-based 1a to the cyclopentenone-based 1cchromophore.

  一系列基于苯基四烯的非线性光学（NLO）染料1a–c被合成并系统研究，这些染料具有相同的供体和受体基团，但四烯桥结构不同，部分通过不同大小的脂肪环相连。三个研究染料中的夹层共轭四烯段分别基于异佛尔酮、(1S)-(−)-蓝桉酮和3,4,4-三甲基-2-环戊烯酮。这种结构改变对这些高极化染料的本征电子结构和物理性质产生了显著影响，这通过多种表征技术得以揭示。与基于异佛尔酮的具有高度结晶特性的染料1a相比，引入蓝桉酮和三甲基环戊烯酮基四烯桥可显著提高染料1b和1c的玻璃形成能力。更重要的是，染料1a–c在吸收带形状、溶剂变色行为以及从紫外-可见-近红外吸收测量得到的能带间隙方面表现出独特的光学特征。采用密度泛函理论（DFT）的量子力学计算也被用于评估这些染料的二阶NLO性质。在极化聚合物中，染料含量为10 wt%时，1a–c的电光（EO）系数从1a的78 pm V−1明显降低到1c的42 pm V−1。这种降低归因于染料分子超极化率（β）的逐渐降低，这与从基于异佛尔酮的1a到基于环戊烯酮的1c染料的渐进式菁菪电子结构有关。
• Dual-channel fluorescent probe bearing two-photon activity for cell viability monitoring
  作者：Yanqian Zhao、Chengkai Zhang、Jiejie Liu、Dandan Li、Xiaohe Tian、Aidong Wang、Shengli Li、Jieying Wu、Yupeng Tian

  DOI：10.1039/c9tb00512a

  日期：——

  We developed a dual-channel two-photon fluorescence probe to monitor cell viability.

  我们开发了一种双通道双光子荧光探针来监测细胞存活。
• PHENYLTETRAENE-BASED NONLINEAR OPTICAL CHROMOPHORES
  申请人：Jen Kwan-Yue

  公开号：US20100029953A1

  公开（公告）日：2010-02-04

  Alkoxy-substituted phenyltetraene nonlinear optically active compounds, films and devices that include the compounds, and methods for making and using the compounds, films, and devices.

  含有烷氧基取代苯基四烯非线性光学活性化合物、包括这些化合物的薄膜和器件，以及制备和使用这些化合物、薄膜和器件的方法。
• Two-photon absorption of styryl-quinolinium, -pyridinium, and -barbituric acid derivatives, and intramolecular charge transfer
  作者：XiaoMei Wang、Chun Wang、WenTao Yu、YuFang Zhou、Xian Zhao、Qi Fang、MinHua Jiang

  DOI：10.1139/v00-188

  日期：2001.2.1

  A series of new chromophores, styryl-parent end-capped with various donors, and with barbituric acid, methyl-pyridinium, and methyl-quinolinium as the acceptors, have been synthesized and characterized by element analysis or X-ray diffraction. Using the Z-scan system, their two-photon absorption (TPA) cross-section values (δ) have been determined under excitation with 10 Hz, and 1064 nm, 35 ps mode-locked Nd:YAG laser pulse in DMF with d_o= 0.05 M. The effective δ value is as high as 10.9 × 10^–48 cm⁴ s per photon for trans-4-(4'-N,N-diphenyl amino) styryl-N-methyl quinolinium iodide (DPASQI). The δ value increases from barbituric acid- to pyridinium- to quinolinium-derivatives apparently due to the increase in both the conjugated degree and planarity; however, when the acceptor is fixed, the δ value increases from dialkyl amino groups to diphenyl amino groups even though the latter is a weaker donor than the dialkyl amino groups. Theoretical calculations confirm that the increased distortion from planarity for the barbituric acid derivative makes its δ value decrease. The relatively large δ value for quinolinium- or pyridinium-derivatives originates from larger intramolecular charge transfer, which can be characterized by the difference of dipole moment (Δµ_ge) between the S₀ and S₁, and the transition dipole moment (M_ee') between S₁ and S₂.Key words: two-photon absorption, intramolecular charge transfer, styryl-quinolinium, styryl-pyridinium, styryl-barbituric acid.

  一系列新的色团，带有各种供体的苯乙烯基母体端封端，以及以巴比妥酸、甲基吡啶盐和甲基喹啉盐为受体的化合物已经合成并通过元素分析或X射线衍射进行了表征。使用Z扫描系统，在10 Hz和1064 nm下，采用35 ps模锁定的Nd:YAG激光脉冲在DMF中激发，其双光子吸收（TPA）截面值（δ）已经确定，其中d_o= 0.05 M。对于反式-4-(4'-N,N-二苯胺基)苯乙烯基-N-甲基喹啉盐（DPASQI），有效的δ值高达10.9 × 10^–48 cm⁴ s每光子。δ值从巴比妥酸到吡啶盐到喹啉盐衍生物显然增加，这可能是由于共轭程度和平面度的增加；然而，当受体固定时，δ值从二烷基氨基团到二苯胺基团增加，尽管后者比二烷基氨基团是一个较弱的供体。理论计算证实，从平面度的增加导致巴比妥酸衍生物的δ值减小。喹啉盐或吡啶盐衍生物的相对较大的δ值源于更大的分子内电荷转移，这可以通过S₀和S₁之间的偶极矩差（Δµ_ge）以及S₁和S₂之间的跃迁偶极矩（M_ee'）来表征。关键词：双光子吸收，分子内电荷转移，苯乙烯基喹啉盐，苯乙烯基吡啶盐，苯乙烯基巴比妥酸。

表征谱图