{4-(2-acetanilidoethenyl)-3-cyano-5,5-dimethyl-2(5H)-furanylidene}propanedinitrile | 712273-63-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: {4-(2-acetanilidoethenyl)-3-cyano-5,5-dimethyl-2(5H)-furanylidene}propanedinitrile
• 英文别名: N-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydrofuran-3-yl)vinyl]-N-phenylacetamide；N-[(E)-2-[4-cyano-5-(dicyanomethylidene)-2,2-dimethylfuran-3-yl]ethenyl]-N-phenylacetamide
• CAS: 712273-63-7
• 化学式: C₂₀H₁₆N₄O₂
• 分子量: 344.373
• InChiKey: TWCWHOMNEXBEET-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-ethanol-2-methylbenzothiazolium iodide 、 {4-(2-acetanilidoethenyl)-3-cyano-5,5-dimethyl-2(5H)-furanylidene}propanedinitrile 在 乙酸酐 、 三乙胺 作用下， 生成 2-[3-cyano-4-[(E,3Z)-3-[3-(2-hydroxyethyl)-1,3-benzothiazol-2-ylidene]prop-1-enyl]-5,5-dimethylfuran-2-ylidene]propanedinitrile
  参考文献：
  名称：

  Synthesis and linear/nonlinear optical properties of a new class of ‘RHS’ NLO chromophore

  摘要：

  已经制备出一种新的双离子型“右侧”梅罗氰胺类化合物，其包含氰基二氰甲基二氢呋喃电子受体。我们的合成方法不仅允许这些色素的简便合成，还能在供体部分及供体与受体系统之间的共轭程度上进行相当大的变化。正如预期的那样，所有这些“右侧”系统都表现出负溶剂色散性，最大波长（极性与非极性溶剂）之间的差异随着共轭程度的增加而增大。符合预期，超拉赖散射（HRS）测量证实，具有最大共轭路径的分子（例如21c、23c）具有最大的首个超极化率βo。此外，我们的HRS评估表明，4-喹啉基腈供体核优于4-吡啶基腈和苯并噻唑基腈系统。我们为一些化合物获得的绩效指标μ(calc)·βo(measured)与文献中报道的最佳“左侧”示例相似。为了展示我们合成技术的多样性，已经制备了这些化合物的代表性聚合物连接衍生物，以及相应的基于TDI的聚氨酯。

  DOI：

  10.1039/b315274j
• 作为产物：
  描述：

  乙酸酐 、 N,N'-二苯甲脒 、 2-(3-氰基-4,5,5-三甲基呋喃-2(5H)-亚甲基)丙二腈 以79%的产率得到{4-(2-acetanilidoethenyl)-3-cyano-5,5-dimethyl-2(5H)-furanylidene}propanedinitrile
  参考文献：
  名称：

  Synthesis and linear/nonlinear optical properties of a new class of ‘RHS’ NLO chromophore

  摘要：

  已经制备出一种新的双离子型“右侧”梅罗氰胺类化合物，其包含氰基二氰甲基二氢呋喃电子受体。我们的合成方法不仅允许这些色素的简便合成，还能在供体部分及供体与受体系统之间的共轭程度上进行相当大的变化。正如预期的那样，所有这些“右侧”系统都表现出负溶剂色散性，最大波长（极性与非极性溶剂）之间的差异随着共轭程度的增加而增大。符合预期，超拉赖散射（HRS）测量证实，具有最大共轭路径的分子（例如21c、23c）具有最大的首个超极化率βo。此外，我们的HRS评估表明，4-喹啉基腈供体核优于4-吡啶基腈和苯并噻唑基腈系统。我们为一些化合物获得的绩效指标μ(calc)·βo(measured)与文献中报道的最佳“左侧”示例相似。为了展示我们合成技术的多样性，已经制备了这些化合物的代表性聚合物连接衍生物，以及相应的基于TDI的聚氨酯。

  DOI：

  10.1039/b315274j

文献信息

• Zwitterionic Non-Linear Optophores And Devices Incorporating Same
  申请人：Kay John Andrew

  公开号：US20070208182A1

  公开（公告）日：2007-09-06

  The invention relates to zwitterionic second order non-linear optophores comprising a compound of general Formula I: wherein D is selected from: and L and R1-R5 are as herein defined. Also, provided are polymeric compositions incorporating these compounds. These optophores display a large and efficient non-linear optical response and therefore can be used in the production of optoelectronic devices.

  本发明涉及带电离子的二次非线性光致移动分子，包括一般式I中的化合物，其中D选自：而L和R1-R5如本文所定义。同时，提供了包含这些化合物的聚合物组合物。这些光致移动分子表现出大而有效的非线性光学响应，因此可以用于光电子器件的生产。
• Tetraanionic Oligo‐Dioxaborines: Strongly Absorbing Near‐Infrared Dyes
  作者：Vladyslav Polishchuk、Andrii Kulinich、Mykola Shandura

  DOI：10.1002/chem.202401097

  日期：——

  Strongly absorbing NIR polymethines of tetraanionic nature bearing 1,3,2-dioxaborine rings and different electron-accepting end-groups were synthesized and characterized. Due to a highly symmetric electronic structure of tetraanionic chromophore, the obtained dyes possess exceptionally high molar absorption coefficients (exceeding half a million) and good fluorescence quantum yields (up to 0.13).

  合成并表征了带有 1,3,2-二氧杂硼环和不同电子接受端基的四阴离子性质的强吸收近红外聚次甲基。由于四阴离子发色团的高度对称电子结构，所获得的染料具有极高的摩尔吸收系数（超过50万）和良好的荧光量子产率（高达0.13）。
• Geometry and bond-length alternation in nonlinear optical materials. II. Effects of donor strength in two push–pull molecules
  作者：Graeme J. Gainsford、M. Delower H. Bhuiyan、Andrew J. Kay

  DOI：10.1107/s0108270108005593

  日期：2008.4.15

  The compounds N-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydrofuran-3-yl)vinyl]-N-phenylacetamide, C(20)H(16)N(4)O(2), (I), and 2-3-cyano-5,5-dimethyl-4-[2-(piperidin-1-yl)vinyl]-2,5-dihydrofuran-2-ylidene}malononitrile 0.376-hydrate, C(17)H(18)N(4)O x 0.376 H(2)O, (II), are novel push-pull molecules. The significant bonding changes in the polyene chain compared with the parent molecule 2-dicyanomethylene-4,5,5-trimethyl-2,5-dihyrofuran-3-carbonitrile are consistent with the relative electron-donating properties of the acetanilido and piperidine groups. The packing of (I) utilizes one phenyl-cyano C-H...N and two phenyl-carbonyl C-H...O hydrogen bonds. Compound (II) crystallizes with a partial water molecule (0.376H(2)O), consistent with cell packing that is dominated by attractive C-H...N(cyano) interactions. These compounds are precursors to novel nonlinear optical chromophores, studied to assess the impact of donor strength and the extent of conjugation on bond-length alternation, crystal packing and aggregation.
• Synthesis and linear/nonlinear optical properties of a new class of ‘RHS’ NLO chromophore
  作者：Andrew J. Kay、Anthony D. Woolhouse、Yuxia Zhao、Koen Clays

  DOI：10.1039/b315274j

  日期：——

  Examples of a new class of zwitterionic, “right-hand side” merocyanines containing a cyanodicyanomethylidenedihydrofuran electron acceptor have been prepared. As well as allowing for the facile synthesis of these chromophores, our synthetic methodology enables considerable variation in both the donor moiety as well as the extent of conjugation between the donor and acceptor systems. As expected, all of these “right-hand side” systems are negatively solvatochromic, with the difference between λmax (polar vs. nonpolar solvents) increasing with the extent of conjugation. In accord with expectations, hyper-Raleigh scattering (HRS) measurements confirm that molecules with the greatest conjugation pathway (for e.g.21c, 23c) have the largest first hyperpolarisabilites, βo. In addition, our HRS evaluation indicates that the 4-quinolinylidene donor nucleus is superior to both the 4-pyridinylidene and benzothiazolylidene systems. The figures of merit, μ(calc).βo(measured), that we obtain for some of these compounds, are of a similar magnitude to the best “left hand side” examples reported in the literature. In order to demonstrate the versatility of our synthetic technique, representative polymer-tetherable derivatives of these compounds have been prepared, as have the corresponding TDI-based polyurethanes.

  已经制备出一种新的双离子型“右侧”梅罗氰胺类化合物，其包含氰基二氰甲基二氢呋喃电子受体。我们的合成方法不仅允许这些色素的简便合成，还能在供体部分及供体与受体系统之间的共轭程度上进行相当大的变化。正如预期的那样，所有这些“右侧”系统都表现出负溶剂色散性，最大波长（极性与非极性溶剂）之间的差异随着共轭程度的增加而增大。符合预期，超拉赖散射（HRS）测量证实，具有最大共轭路径的分子（例如21c、23c）具有最大的首个超极化率βo。此外，我们的HRS评估表明，4-喹啉基腈供体核优于4-吡啶基腈和苯并噻唑基腈系统。我们为一些化合物获得的绩效指标μ(calc)·βo(measured)与文献中报道的最佳“左侧”示例相似。为了展示我们合成技术的多样性，已经制备了这些化合物的代表性聚合物连接衍生物，以及相应的基于TDI的聚氨酯。