(E)-1-(2-hydroxyethyl)-4-(2-(1-methylpyridin-1-ium-4-yl)vinyl)-3-propyl-1H-pyrazol-5-olate | 895552-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (E)-1-(2-hydroxyethyl)-4-(2-(1-methylpyridin-1-ium-4-yl)vinyl)-3-propyl-1H-pyrazol-5-olate
• CAS: 895552-16-6
• 化学式: C₁₆H₂₁N₃O₂
• 分子量: 287.362
• InChiKey: CTJQUCSKKCOLPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxyethyl)-4-(2-(1-methylpyridin-1-ium-4-yl)vinyl)-3-propyl-1H-pyrazol-5-olate 、 3-({4-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydrofuran-2-yl)vinyl]phenyl}methylamino)propionic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  Antiparallel-Aligned Neutral-Ground-State and Zwitterionic Chromophores as a Nonlinear Optical Material

  摘要：

  Efficient noncentrosymmetric arrangement of nonlinear optical (NLO) chromophores with high first-order hyperpolarizability (beta) for increased electro-optical (EO) efficiency has proven challenging as strong dipolar interactions between the chromophores encourage antiparallel alignment, attenuating the macroscopic EO effect. This work explores a novel approach to simultaneously achieve large beta values while providing an adjustable dipole moment by linking a strong neutral-ground-state (NGS) NLO chromophore with positive beta to a zwitterionic (ZWI) chromophore with negative beta in an antiparallel fashion. It is proposed that the overall beta of such a structure will be the sum of the absolute values of the two types of chromophores while the dipole moment will be the difference. Molecules 1-3 were synthesized to test the feasibility of this approach. Molecular dynamics calculations and NMR data supported that the NGS chromophore component and the ZWI chromophore component self-assemble to an antiparallel conformation in chloroform. Calculations showed that the dipole moment of 1 is close to the difference of the two component chromophores. Hyper-Rayleigh scattering (HRS) studies confirmed that the first hyperpolarizability of 1 is close to the sum of the two component chromophores. These results support the idea that an antiparallel-aligned neutral-ground-state chromophore and a zwitterionic chromophore can simultaneously achieve an increase in beta and a decrease of the dipole moment.

  DOI：

  10.1021/ja057903i
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 (E)-1-(2-hydroxyethyl)-4-(2-(1-methylpyridin-1-ium-4-yl)vinyl)-3-propyl-1H-pyrazol-5-olate
  参考文献：
  名称：

  Antiparallel-Aligned Neutral-Ground-State and Zwitterionic Chromophores as a Nonlinear Optical Material

  摘要：

  Efficient noncentrosymmetric arrangement of nonlinear optical (NLO) chromophores with high first-order hyperpolarizability (beta) for increased electro-optical (EO) efficiency has proven challenging as strong dipolar interactions between the chromophores encourage antiparallel alignment, attenuating the macroscopic EO effect. This work explores a novel approach to simultaneously achieve large beta values while providing an adjustable dipole moment by linking a strong neutral-ground-state (NGS) NLO chromophore with positive beta to a zwitterionic (ZWI) chromophore with negative beta in an antiparallel fashion. It is proposed that the overall beta of such a structure will be the sum of the absolute values of the two types of chromophores while the dipole moment will be the difference. Molecules 1-3 were synthesized to test the feasibility of this approach. Molecular dynamics calculations and NMR data supported that the NGS chromophore component and the ZWI chromophore component self-assemble to an antiparallel conformation in chloroform. Calculations showed that the dipole moment of 1 is close to the difference of the two component chromophores. Hyper-Rayleigh scattering (HRS) studies confirmed that the first hyperpolarizability of 1 is close to the sum of the two component chromophores. These results support the idea that an antiparallel-aligned neutral-ground-state chromophore and a zwitterionic chromophore can simultaneously achieve an increase in beta and a decrease of the dipole moment.

  DOI：

  10.1021/ja057903i