4-(1'-methylpyridinio-4'-yl)phenolate | 143213-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1'-methylpyridinio-4'-yl)phenolate
• 英文别名: 4-[N-methyl-4-pyridinio]-phenolate；4-(phenyloxido)-N-methylpyridinium；4-(1-Methylpyridin-4(1H)-ylidene)cyclohexa-2,5-dien-1-one；4-(1-methylpyridin-4-ylidene)cyclohexa-2,5-dien-1-one
• CAS: 143213-08-5
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: JXVBLESYBMPMGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-碘吡啶 在 四(三苯基膦)钯 盐酸 、 正丁基锂 、 四丁基氢氧化铵 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 为溶剂， 生成 4-(1'-methylpyridinio-4'-yl)phenolate
  参考文献：
  名称：

  Synthesis of 4-[N-methyl-4-pyridinio]-phenolate (POMP) and negative solvatochromism of this model molecule in view of nonlinear optical applications

  摘要：

  -4-[N-Methyl-4-pyridiniol-phenolate or [4-(phenyloxido)-N-methylpyridinium, POMP] has been synthesized via Suzuki cross-coupling reaction. POMP undergoes a strong negative solvatochromism (blue shift) as the solvent polarity increases and behaves qualitatively as the famous empirical polarity parameter ET(30). However, it should be noted that the previously published theoretical investigations of POMP revealed unexpected difficulties in the interpretation of its structure. Interestingly, it is confirmed here in the sense that the experimental transition energy in nonpolar solvents seems by far less important than predicted by different computational methods. Therefore, POMP is highly prospective for (i) the comprehension of betaines solvatochromism, (ii) the development of new molecules with large first and second hyperpolarizabilities useful for doping polymers, the aim being to elaborate efficient processable materials for quadratic optics. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.031

文献信息

• Syntheses of Sterically Hindered Pyridinium Phenoxides as Model Compounds in Nonlinear Optics
  作者：Vincent Diemer、Hélène Chaumeil、Albert Defoin、Alain Fort、Alex Boeglin、Christiane Carré

  DOI：10.1002/ejoc.200600030

  日期：2006.6

  increase in the twist angle between the two aromatic rings leads to an enhancement of the NLO properties. In order to confirm this feature experimentally, it was necessary to prepare a series of new hindered pyridinium phenoxides. Their efficient syntheses by Suzuki cross-coupling reactions are described herein.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  具有 π 共轭系统的非中心对称分子，其中包括苯酚吡啶等推挽分子，由于其非线性光学 (NLO) 特性，是一类有前途的新型光电子材料。建模研究表明，两个芳环之间扭曲角的增加导致 NLO 性能的增强。为了通过实验证实这一特征，有必要制备一系列新的受阻吡啶酚盐。本文描述了它们通过 Suzuki 交叉偶联反应的有效合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Synthesis of 4-[N-methyl-4-pyridinio]-phenolate (POMP) and negative solvatochromism of this model molecule in view of nonlinear optical applications
  作者：Vincent Diemer、Hélène Chaumeil、Albert Defoin、Patrice Jacques、Christiane Carré

  DOI：10.1016/j.tetlet.2005.05.031

  日期：2005.7

  -4-[N-Methyl-4-pyridiniol-phenolate or [4-(phenyloxido)-N-methylpyridinium, POMP] has been synthesized via Suzuki cross-coupling reaction. POMP undergoes a strong negative solvatochromism (blue shift) as the solvent polarity increases and behaves qualitatively as the famous empirical polarity parameter ET(30). However, it should be noted that the previously published theoretical investigations of POMP revealed unexpected difficulties in the interpretation of its structure. Interestingly, it is confirmed here in the sense that the experimental transition energy in nonpolar solvents seems by far less important than predicted by different computational methods. Therefore, POMP is highly prospective for (i) the comprehension of betaines solvatochromism, (ii) the development of new molecules with large first and second hyperpolarizabilities useful for doping polymers, the aim being to elaborate efficient processable materials for quadratic optics. (c) 2005 Elsevier Ltd. All rights reserved.