5-[(E)-2-[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]ethenyl]thiophene-2-carbaldehyde | 1042978-37-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-[(E)-2-[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]ethenyl]thiophene-2-carbaldehyde
• CAS: 1042978-37-9
• 化学式: C₂₇H₂₃NO₃S
• 分子量: 441.551
• InChiKey: XRNQWNKIVKWLBJ-FZSIALSZSA-N

物化性质

• 沸点：
  639.7±55.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-二乙基-2-硫代巴比妥酸 、 5-[(E)-2-[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]ethenyl]thiophene-2-carbaldehyde 在 三乙胺 作用下， 以50%的产率得到1,3-diethyl-5-[[5-[(E)-2-[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]ethenyl]thiophen-2-yl]methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
  参考文献：
  名称：

  Thermally stable triaryl amino chromophores with high molecular hyperpolarizabilities

  摘要：

  The synthesis of a series of high temperature triaryl amino chromophores with unprecedented hyperpolarizability values for potential EO applications is described. 4-(N,N-di-p-anisylamino)phenyl donors are for the first time bridged to powerful acceptors such as tricyanovinyldihydrofuran via vinyl thiophene linkages. The chromophores are readily soluble in common organic solvents, exhibit useful absorptions and high thermal decomposition temperatures (highest T-d = 358 degreesC). Molecular hyperpolarizabilities (beta) of the chromophores were measured by Hyper Rayleigh Scattering (HRS) at 1604 nm, which gave beta values from 1000 to 20,000 x 10(-30) esu. The elect rochemical behavior of the chromophores were Studied by cyclic voltametry, and agree well with the intrinsic nonlinearities observed. These chromophores are of particular interest due to their large optical nonlinearities, transparency in the near IR, high thermal decomposition temperatures, and their potential to be incorporated into polymeric materials. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.125
• 作为产物：
  描述：

  4,4-二甲氧基三苯胺 在 正丁基锂 、 potassium tert-butylate 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5-[(E)-2-[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]ethenyl]thiophene-2-carbaldehyde
  参考文献：
  名称：

  Thermally stable triaryl amino chromophores with high molecular hyperpolarizabilities

  摘要：

  The synthesis of a series of high temperature triaryl amino chromophores with unprecedented hyperpolarizability values for potential EO applications is described. 4-(N,N-di-p-anisylamino)phenyl donors are for the first time bridged to powerful acceptors such as tricyanovinyldihydrofuran via vinyl thiophene linkages. The chromophores are readily soluble in common organic solvents, exhibit useful absorptions and high thermal decomposition temperatures (highest T-d = 358 degreesC). Molecular hyperpolarizabilities (beta) of the chromophores were measured by Hyper Rayleigh Scattering (HRS) at 1604 nm, which gave beta values from 1000 to 20,000 x 10(-30) esu. The elect rochemical behavior of the chromophores were Studied by cyclic voltametry, and agree well with the intrinsic nonlinearities observed. These chromophores are of particular interest due to their large optical nonlinearities, transparency in the near IR, high thermal decomposition temperatures, and their potential to be incorporated into polymeric materials. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.125

文献信息

• Molecular Engineering of Organic Sensitizers for Dye-Sensitized Solar Cell Applications
  作者：Daniel P. Hagberg、Jun-Ho Yum、HyoJoong Lee、Filippo De Angelis、Tannia Marinado、Karl Martin Karlsson、Robin Humphry-Baker、Licheng Sun、Anders Hagfeldt、Michael Grätzel、Md. K. Nazeeruddin

  DOI：10.1021/ja800066y

  日期：2008.5.1

  Novel unsymmetrical organic sensitizers comprising donor, electron-conducting, and anchoring groups were engineered at a molecular level and synthesized for sensitization of mesoscopic titanium dioxide injection solar cells. The unsymmetrical organic sensitizers 3-(5-(4-(diphenylamino)styryl)thiophen-2-yl)-2-cyanoacrylic acid (D5), 3-(5-bis(4-(diphenylamino)styryl)thiophen-2-yl)-2-cyanoacrylic acid

  在分子水平上设计并合成了包含供体、电子传导和锚定基团的新型不对称有机敏化剂，用于介观二氧化钛注入太阳能电池的敏化。不对称有机增感剂 3-(5-(4-(diphenylamino)styryl)thiophen-2-yl)-2-cyanoacrylic acid (D5), 3-(5-bis(4-(diphenylamino)styryl)thiophen-2-)基)-2-氰基丙烯酸(D7)、5-(4-(双(4-甲氧基苯基氨基)苯乙烯基)噻吩-2-基)-2-氰基丙烯酸(D9)和3-(5-双(4， 4'-二甲氧基二苯基氨基）苯乙烯基）噻吩-2-基）-2-氰基丙烯酸（D11）固定在 TiO2 上，并在具有挥发性电解质的染料敏化太阳能电池中进行了测试。这些敏化剂的单色入射光子到电流的转换效率在 80% 以上，D11 敏化太阳能电池产生的短路光电流密度为 13。90 +/- 0.2 mA/cm(2)、740