1-ethyl-6-formyl-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline | 76495-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-ethyl-6-formyl-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-Ethyl-2,2,4,7-tetramethyl-3,4-dihydroquinoline-6-carbaldehyde
• CAS: 76495-90-4
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: OTLLJLZAXQGLEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  异佛尔酮 、 1-ethyl-6-formyl-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以72%的产率得到
  参考文献：
  名称：

  Push–pull tetraene chromophores derived from dialkylaminophenyl, tetrahydroquinolinyl and julolidinyl moieties: optimization of second-order optical nonlinearity by fine-tuning the strength of electron-donating groups

  摘要：

  一系列高度可极化的色素1–3已经合成，这些色素基于三种不同类型的电子供体，包括二乙基氨基苯基、四氢喹啉基和朱洛啉基，分别具有相同的基于异佛尔酮的四烯桥和强CF3–TCF接受体。这些色素逐渐增强的电子供给强度使得其分子基态极化能力能够进行精细调节，在局部介电环境和极化诱导的非中心有序情况下，接近于极大的超极化率（β）的最佳状态。溶剂色谱研究和DFT计算表明，具有更强供体基团的偶极色素2和3可以在最极性溶剂中被极化到接近青苯极限，甚至超越这一极限，进入双性离子范围，从而展现出反向溶剂色谱现象，并降低β值。这与在所有测试溶剂中具有二乙基氨基苯基供体的1的多烯特性形成鲜明对比。更引人注目的是，电场极化在其极化薄膜中引起了色素电荷转移吸收带的位置、强度和形状的显著变化。因此，这表明固态中复杂的分子间相互作用可以改变作用于极化和去极化薄膜中色素的反应场，并显著影响其可实现的电光（EO）活性。因此，含有10 wt%色素的客-主聚合物在PMMA中显示出1/PMMA和2/PMMA的EO系数约为80 pm V^-1，而3/PMMA则急剧下降至20 pm V^-1。这些系统分析导致了一种新型客-主电光聚合物的合理设计，该聚合物含有35 wt%空间修饰的色素AJLZ55，在1.31 μm下表现出超高的EO系数218 pm V^-1。

  DOI：

  10.1039/c2jm32848h

文献信息

• Push–pull tetraene chromophores derived from dialkylaminophenyl, tetrahydroquinolinyl and julolidinyl moieties: optimization of second-order optical nonlinearity by fine-tuning the strength of electron-donating groups
  作者：Xing-Hua Zhou、Jingdong Luo、Joshua A. Davies、Su Huang、Alex K. Y. Jen

  DOI：10.1039/c2jm32848h

  日期：——

  A series of highly polarizable chromophores 1–3 has been synthesized based on three different types of electron donors, including diethylaminophenyl, tetrahydroquinolinyl and julolidinyl groups respectively, with the same isophorone-derived tetraene bridges and strong CF3–TCF acceptors. The progressively increased electron-donating strength for these chromophores allows for the fine-tuning of their molecular ground-state polarization, being very close to optimal for very large hyperpolarizability (β), as a function of the local dielectric environment and poling-induced acentric ordering. The solvatochromic study and DFT calculations suggested that more dipolar chromophores 2 and 3 with stronger donating groups can be polarized quite close to the cyanine limit, or even beyond that into the zwitterionic regime in the most polar solvents to give the inverted solvatochromism and diminished β values. This is in stark contrast to the polyene-like characteristic of 1 with the diethylaminophenyl donor in all the tested solvents. Most intriguingly, the electric field poling has induced significant changes in the position, intensity and shape of the chromophoric charge-transfer absorption band in their poled thin films. It is thus indicated that the nontrivial intermolecular interaction in solid state can vary the reaction field that acts on the chromophores in poled and depoled films, and significantly affect their achievable electro-optic (EO) activities. As a result, the guest–host polymers containing 10 wt% of chromophores in PMMA showed EO coefficients of ∼80 pm V−1 for 1/PMMA and 2/PMMA, while dramatically dropping to 20 pm V−1 for 3/PMMA. These systematic analyses led to the rational design of a new guest–host EO polymer incorporating 35 wt% of a spatially modified chromophore AJLZ55, which gave ultrahigh EO coefficients of 218 pm V−1 at 1.31 μm.

  一系列高度可极化的色素1–3已经合成，这些色素基于三种不同类型的电子供体，包括二乙基氨基苯基、四氢喹啉基和朱洛啉基，分别具有相同的基于异佛尔酮的四烯桥和强CF3–TCF接受体。这些色素逐渐增强的电子供给强度使得其分子基态极化能力能够进行精细调节，在局部介电环境和极化诱导的非中心有序情况下，接近于极大的超极化率（β）的最佳状态。溶剂色谱研究和DFT计算表明，具有更强供体基团的偶极色素2和3可以在最极性溶剂中被极化到接近青苯极限，甚至超越这一极限，进入双性离子范围，从而展现出反向溶剂色谱现象，并降低β值。这与在所有测试溶剂中具有二乙基氨基苯基供体的1的多烯特性形成鲜明对比。更引人注目的是，电场极化在其极化薄膜中引起了色素电荷转移吸收带的位置、强度和形状的显著变化。因此，这表明固态中复杂的分子间相互作用可以改变作用于极化和去极化薄膜中色素的反应场，并显著影响其可实现的电光（EO）活性。因此，含有10 wt%色素的客-主聚合物在PMMA中显示出1/PMMA和2/PMMA的EO系数约为80 pm V^-1，而3/PMMA则急剧下降至20 pm V^-1。这些系统分析导致了一种新型客-主电光聚合物的合理设计，该聚合物含有35 wt%空间修饰的色素AJLZ55，在1.31 μm下表现出超高的EO系数218 pm V^-1。