3-[4-(二丁基氨基)苯基]丙烯醛 | 90134-11-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 3-[4-(二丁基氨基)苯基]丙烯醛
• 英文名称: 4-(dibutylamino)cinnamaldehyde
• 英文别名: 3-(N,N-dibutylaminophenyl)acrolein；(E)-3-[4-(dibutylamino)phenyl]prop-2-enal
• CAS: 90134-11-5
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: STAKZSAWJOSDML-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[4-(二丁基氨基)苯基]丙烯醛 在 盐酸 、 18-冠醚-6 、 水 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 63.0h， 生成 2,4,6,8-壬四烯醛,9-[4-(二丁基氨基)苯基]-,(2E,4E,6E,8E)-
  参考文献：
  名称：

  Amphiphilic polyenic push–pull chromophores for nonlinear optical applications

  摘要：

  两亲阳离子多烯推拉发色团为二次谐波的产生提供了有趣的超分子可能性，我们合成了这种发色团，并首次在溶液中通过电场诱导二次谐波（EFISH）的产生对其光学非线性进行了研究。

  DOI：

  10.1039/a908717f
• 作为产物：
  描述：

  (E)-ethyl 3-(4-aminophenyl)acrylate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 生成 3-[4-(二丁基氨基)苯基]丙烯醛
  参考文献：
  名称：

  Charge-shift probes of membrane potential. Synthesis

  摘要：

  DOI：

  10.1021/jo00188a006

文献信息

• [EN] NONLINEAR OPTICAL COMPOUNDS AND METHODS FOR THEIR PREPARATION<br/>[FR] COMPOSES OPTIQUES NON LINEAIRES ET PROCEDES DE FABRICATION
  申请人：UNIV WASHINGTON

  公开号：WO2004065384A1

  公开（公告）日：2004-08-05

  Nonlinear optically active compounds, methods for making nonlinear optically active compounds, compounds useful for making nonlinear optically active compounds, methods for making compounds useful for making nonlinear optically active compounds, macrostructures tha tinclude nonlinear optically active components, and devices including the nonlinear optically active compounds and the macrostructures.

  非线性光学活性化合物，制备非线性光学活性化合物的方法，用于制备非线性光学活性化合物的化合物，制备用于制备非线性光学活性化合物的化合物的方法，包括非线性光学活性组分的宏观结构，以及包括非线性光学活性化合物和宏观结构的器件。
• Intramolecular Electron Density Redistribution upon Hydrogen Bond Formation in the Anion Methyl Orange at the Water/1,2-Dichloroethane Interface Probed by Phase Interference Second Harmonic Generation
  作者：Juliette Rinuy、Alexis Piron、Pierre Franc˛ois Brevet、Mireille Blanchard-Desce、Hubert H. Girault

  DOI：10.1002/1521-3765(20000915)6:18<3434::aid-chem3434>3.0.co;2-l

  日期：2000.9.15

  Surface second harmonic generation (SSHG) studies of the azobenzene derivative p-dimethylaminoazobenzene sulfonate, often referred as Methyl Orange (MO), at the neat water/1,2-dichloroethane (DCE) interface is reported. The two forms of the anionic MO dye, which are usually observed in bulk solution, with one form being hydrogen bonded to a water molecule through the azo nitrogens (MO/H2O) and the

  据报道，在纯水/ 1,2-二氯乙烷（DCE）界面上，对偶氮苯衍生物对二甲基氨基偶氮苯磺酸盐（通常称为甲基橙（MO））进行表面二次谐波生成（SSHG）研究。阴离子型MO染料的两种形式通常在本体溶液中观察到，一种形式是通过偶氮氮（MO / H2O）氢键合到水分子上，另一种形式没有氢键（MO）。在水/ DCE界面观察到。它们的平衡常数已与相应的本体溶液进行了比较，发现相同。两种形式的吸附平衡已确定，两种形式的吸附的吉布斯能量均测得为-30 kJMOl（-1）。根据SH信号的光偏振分析，在角度分布的狄拉克δ函数的假设下，MO跃迁偶极矩的定向角对于MO为34 +/- 2度，对于MO / 为43 +/- 2度，其差异由两种形式的溶剂化特性不同。此外，对这些数据的波长依赖性分析表明，在与水分子形成氢键时，由于水合阴离子形式内电子密度的重新分布而产生的干涉图样。在界面处使用另一种染料，以定义对两种形
• Optical and electrochemical properties of soluble donor-π-donor compounds as potential molecular wires and electrochemically-triggered optical switches
  作者：Laurent Porrès、Valérie Alain、Laurent Thouin、Philippe Hapiot、Mireille Blanchard-Desce

  DOI：10.1039/b305737b

  日期：——

  With the aim of designing molecular wires operating at easily accessible potentials, a series of soluble bis-donor polyenic compounds (up to 3.2 nm long) has been prepared. Their optical and electrochemical properties have been investigated. These model compounds were shown to exhibit a reversible two-electron oxidation process at low potential (which further decreases with increasing polyenic chain length). The oxidized dicationic species combine convenient stability and solubility. Interestingly, these species also show reduced bond length alternation along the polyenic chain, consistent with a significant red-shift of their absorption band to the NIR region. Such behaviour is expected to lead to a dramatic enhancement of the third-order nonlinear optical responses of the polyenic molecules upon oxidation, opening the way to optical switches. Hence, such molecules represent promising model compounds for molecular wires but also open an innovative route towards voltage-driven optical switches.

  为了设计在易于接近的电势下工作的分子线，制备了一系列可溶性双供体多烯化合物（长达 3.2 nm）。对其光学和电化学性质进行了研究。这些模型化合物在低电位下表现出可逆的双电子氧化过程（随着多烯链长度的增加而进一步降低）。氧化双阳离子物质结合了便利的稳定性和溶解度。有趣的是，这些物质还显示出沿着多烯链的键长交替减少，这与它们的吸收带向近红外区域的显着红移一致。这种行为预计将导致氧化时多烯分子的三阶非线性光学响应的​​显着增强，从而为光开关开辟道路。因此，此类分子代表了分子线的有前途的模型化合物，同时也开辟了一条通向电压驱动光开关的创新途径。
• Large Quadratic Hyperpolarizabilities with Donor–Acceptor Polyenes Exhibiting Optimum Bond Length Alternation: Correlation Between Structure and Hyperpolarizability
  作者：M. Blanchard-Desce、V. Alain、P. V. Bedworth、S. R. Marder、A. Fort、C. Runser、M. Barzoukas、S. Lebus、R. Wortmann

  DOI：10.1002/chem.19970030717

  日期：1997.7

  AbstractDonor–acceptor polyenes of various lengths, and that combine aromatic electron‐donating moieties with powerful heterocyclic electron‐withdrawing terminal groups, have been synthesized and characterized as efficient nonlinear optical (NLO) chromophores. Their linear and nonlinear optical properties have been investigated, and variations in these properties have been related to ground‐state polarization (dipole μ) and structure. In particular, unprecedented quadratic hyperpolarizabilities (β) have been achieved (up to β(0) = 1500 × 10−30 esu) by reduction of the bond‐length alternation (BLA) in the polyenic chain. In each series of homologous compounds, increasing the number n of conjugated double bonds in the polyenic chain results in a marked bathochromic shift, more pronounced BLA, and exponential increases in μβ(0) values. As a result, polyenic chromophores displaying excellent optical quadratic nonlinearities (μβ values as large as 100 times that of the quadratic NLO benchmark 4‐dimethyl‐amino‐4′‐nitrostilbene (DANS)), as well as satisfactory solubility, have been obtained.
• MAEHDA, SYUITI;KUROSEH, YUTAKA;KIMURA, TAKASIRO;NAKAKUKI, ATSUKO
  作者：MAEHDA, SYUITI、KUROSEH, YUTAKA、KIMURA, TAKASIRO、NAKAKUKI, ATSUKO

  DOI：——

  日期：——