N,N-bis(4-methoxyphenyl)-5-(2-(thiophen-2-yl)vinyl)thiophen-2-amine | 1042150-10-6

• 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: N,N-bis(4-methoxyphenyl)-5-(2-(thiophen-2-yl)vinyl)thiophen-2-amine
• CAS: 1042150-10-6
• 化学式: C₂₄H₂₁NO₂S₂
• 分子量: 419.568
• InChiKey: AEQOFVMCEHHAMX-UHFFFAOYSA-N

物化性质

• 沸点：
  600.7±55.0 °C(predicted)
• 密度：
  1.268±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  正丁基锂 、 N,N-bis(4-methoxyphenyl)-5-(2-(thiophen-2-yl)vinyl)thiophen-2-amine 在 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 以67 %的产率得到5-(2-(5-(bis(4-methoxyphenyl)amino)thiophen-2-yl)vinyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  提高具有噻吩-2-胺衍生供体基团的二阶非线性光学发色团的电光性能

  摘要：

  已经合成了两种创新的二阶非线性光学发色团，称为 B-C，其特征是噻吩衍生的供体和三氰基乙烯基二氢呋喃桥作为受体。这些发色团已经过全面的表征。值得注意的是，发色团 B–C 的供体成分分别是（甲基（苯基）氨基）噻吩和（4-甲氧基苯氨基）噻吩，与发色团 A 中存在的二乙氨基苯基单元相反。密度泛函理论计算表明，第一个超极化率具有（甲氧基苯基氨基）噻吩供体的发色团C的电子给电子能力比发色团A和B高约60％。这表明仅用噻吩取代苯环并不能显着增强供体的给电子能力。掺杂有 25 wt% 发色团 AC 的聚合物薄膜的 r33 值分别为 39 pm/V、46 pm/V 和 76 pm/V。发色团B和C的电光系数分别比发色团A高18%和95%。这些发现证实，噻吩衍生的供体，特别是具有多个杂原子的供体，可以有效增强发色团的电光系数。

  DOI：

  10.1016/j.dyepig.2024.112379
• 作为产物：
  描述：

  5-(bis(4-methoxyphenyl)amino)thiophene-2-carbaldehyde 、 (2-噻吩基甲基)三苯基溴化膦 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以75 %的产率得到N,N-bis(4-methoxyphenyl)-5-(2-(thiophen-2-yl)vinyl)thiophen-2-amine
  参考文献：
  名称：

  提高具有噻吩-2-胺衍生供体基团的二阶非线性光学发色团的电光性能

  摘要：

  已经合成了两种创新的二阶非线性光学发色团，称为 B-C，其特征是噻吩衍生的供体和三氰基乙烯基二氢呋喃桥作为受体。这些发色团已经过全面的表征。值得注意的是，发色团 B–C 的供体成分分别是（甲基（苯基）氨基）噻吩和（4-甲氧基苯氨基）噻吩，与发色团 A 中存在的二乙氨基苯基单元相反。密度泛函理论计算表明，第一个超极化率具有（甲氧基苯基氨基）噻吩供体的发色团C的电子给电子能力比发色团A和B高约60％。这表明仅用噻吩取代苯环并不能显着增强供体的给电子能力。掺杂有 25 wt% 发色团 AC 的聚合物薄膜的 r33 值分别为 39 pm/V、46 pm/V 和 76 pm/V。发色团B和C的电光系数分别比发色团A高18%和95%。这些发现证实，噻吩衍生的供体，特别是具有多个杂原子的供体，可以有效增强发色团的电光系数。

  DOI：

  10.1016/j.dyepig.2024.112379

文献信息

• Rational Enhancement of Second-Order Nonlinearity: Bis-(4-methoxyphenyl)<i>hetero</i>-aryl-amino Donor-Based Chromophores: Design, Synthesis, and Electrooptic Activity
  作者：Joshua A. Davies、Arumugasamy Elangovan、Philip A. Sullivan、Benjamin C. Olbricht、Denise H. Bale、Todd R. Ewy、Christine M. Isborn、Bruce E. Eichinger、Bruce H. Robinson、Philip J. Reid、Xiaosong Li、Larry R. Dalton

  DOI：10.1021/ja8007424

  日期：2008.8.13

  Two new highly hyperpolarizable chromophores, based on NN-bis-(4-methoxyphenyl)aryl-amino donors and phenyl-trifluoromethyl-tricyanofuran (CF3-Ph-TCF) acceptor linked together via pi-conjugation through 2,5-divinylenethienyl moieties as the bridge, have been designed and synthesized successfully for the first time. The aryl moieties on the donor side of the chromophore molecules were varied as to be thiophene and 1-n-hexylpyrrole. The linear and nonlinear optical (NLO) properties of all compounds were evaluated in addition to recording relevant thermal and electrochemical data. The properties of the two new molecules were comparatively studied. These results are critically analyzed along with two other compounds, reported earlier from our laboratories and our collaborator's, that contain (i) aliphatic chain-bearing aniline and (ii) dianisylaniline as donors, keeping the bridge (2,5-divinylenethienyl-), and the acceptor (CF3-Ph-TCF), constant. Trends in theoretically (density functional theory, DFT) predicted, zero-frequency gas-phase hyperpolarizability [beta(0;0,0)] values are shown to be consistent with the trends in beta HRS(-2 omega;omega,omega), as measured by Hyper-Rayleigh Scattering (HRS), when corrected to zero-frequency using the two-level model (TLM) approximation. Similarly, trends in poling efficiency data (r(33)/E-p) and wavelength dispersion measured by reflection ellipsometry (using a Teng-Man apparatus) and attenuated total reflection (ATR) are found to fit the TLM and DFT predictions. A fold enhancement in bulk nonlinearity (r(33)) is realized as the donor subunits are changed from alkylaniline to dianisylaminopyrrole donors. The results of these studies provide insight into the complicated effects on molecular hyperpolarizability of substituting heteroaromatic subunits into the donor group structures. These studies also demonstrate that, when frequency dependence and electric-field-induced ordering behavior are correctly accounted for, ab initio DFT generated beta(0;0,0) is effective as a predictor of changes in r33 behavior based on chromophore structure modification. Thus DFT can provide valuable insight into the electronic structure origin of complex optical phenomena in organic media.