N-methyl-4,4'-bipyridinium chloride monohydrate | 1238138-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-methyl-4,4'-bipyridinium chloride monohydrate
• 英文别名: MQCl*H2O
• CAS: 1238138-74-3
• 化学式: C₁₁H₁₁N₂*Cl*H₂O
• 分子量: 224.69
• InChiKey: KEKPGAMNBRFQPU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.25
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.27
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-methyl-4,4'-bipyridinium chloride monohydrate 、 zinc(II) chloride 以 水 为溶剂， 生成 [(N-methyl-4,4'-bipyridinium)ZnCl3]
  参考文献：
  名称：

  Photochromic Metal Complexes of N-Methyl-4,4′-Bipyridinium: Mechanism and Influence of Halogen Atoms

  摘要：

  Photochromism of N-methyl-4,4'-bipyridinium (MQ(+)) salts and their metal complexes has never been reported. A series of MQ(+) coordinated halozinc complexes [(MQ)ZnX3] (X = Cl (1), Br (2), I (3)) and [(MQ)ZnCl1.53I1.47](2)(MQ)ZnCl1.68I1.32 (4), with better physicochemical stability than halide salts of the MQ(+) cation, have been found to exhibit different photochromic behaviors. Compounds 1-3 are isostructural, but only 1 and 2 show photochromism. Introduction of partial Cl atoms to nonphotochromic compound 3 yields compound 4, which also displays photochromism. The photochromic response of 1, 2, and 4 indicates the presence of their long-lived charge separation states, which originate from X -> MQ(+) electron transfer according to ESR and XPS measurements. Studies on the influence of different coordinated halogen atoms demonstrate that the Cl atom may be a more suitable electron donor than Br and I atoms to design redox photochromic metal complexes.

  DOI：

  10.1021/ic2020868

文献信息

• Syntheses and Spectroscopic and Quadratic Nonlinear Optical Properties of Extended Dipolar Complexes with Ruthenium(II) Ammine Electron Donor and <i>N</i>-Methylpyridinium Acceptor Groups
  作者：Benjamin J. Coe、Lathe A. Jones、James A. Harris、Bruce S. Brunschwig、Inge Asselberghs、Koen Clays、André Persoons、Javier Garín、Jesús Orduna

  DOI：10.1021/ja0315412

  日期：2004.3.1

  In this paper, we describe the extremely unusual optical properties of Ru(II)-based electron donor-acceptor (D-A) polyene and some closely related chromophores. For three different polyene series, the intense, visible d-->pi* metal-to-ligand charge-transfer bands unexpectedly blue-shift as the number of E-ethylene units (n) increases from 1 to 3, and the static first hyperpolarizabilities beta(0) determined

  在本文中，我们描述了基于 Ru(II) 的电子供体-受体 (DA) 多烯和一些密切相关的发色团的极其不寻常的光学性质。对于三种不同的多烯系列，随着 E-乙烯单元 (n) 的数量从 1 增加到 3，强烈的、可见的 d-->pi* 金属-配体电荷转移带出人意料地蓝移，并且静电首先通过超瑞利散射和斯塔克光谱确定的超极化率 beta(0) 在 n = 2 时最大化，与其他已知的 DA 多烯形成鲜明对比，其中 beta(0) 随 n 稳定增加。瞬态密度泛函理论和有限场计算验证了这些经验趋势，这些趋势源于复合物的轨道结构。
• Pentacyanoiron(II) as an Electron Donor Group for Nonlinear Optics:  Medium-Responsive Properties and Comparisons with Related Pentaammineruthenium(II) Complexes
  作者：Benjamin J. Coe、Josephine L. Harries、Madeleine Helliwell、Lathe A. Jones、Inge Asselberghs、Koen Clays、Bruce S. Brunschwig、James A. Harris、Javier Garín、Jesús Orduna

  DOI：10.1021/ja063449m

  日期：2006.9.1

  In this article, we describe a series of complex salts in which electron-rich Fe-II(CN)(5)}(3-) centers are coordinated to pyridyl ligands with electron-accepting N-methyl/aryl-pyridinium substituents. These compounds have been characterized by using various techniques including electronic absorption spectroscopy and cyclic voltammetry. Molecular quadratic nonlinear optical (NLO) responses have been determined by using hyper-Rayleigh scattering (HRS) at 1064 nm, and also via Stark (electroabsorption) spectroscopic studies on the intense, visible d -> pi* metal-to-ligand charge-transfer (MLCT) bands. The relatively large static first hyperpolarizabilities, beta(0), increase markedly on moving from aqueous to methanol solutions, accompanied by large red-shifts in the MLCT transitions. Acidification of aqueous solutions allows reversible switching of the linear and NLO properties, as shown via both HRS and Stark experiments. Time-dependent density functional theory and finite field calculations using a polarizable continuum model yield relatively good agreement with the experimental results and confirm the large decrease in beta(0) on protonation. The Stark-derived beta(0) values are generally larger for related Ru-II(NH3)(5)}(2+) complexes than for their Fe-II(CN) (5)} (3-) analogues, consistent with the HRS data in water. However, the HRS data in methanol show that the stronger solvatochromism of the Fe-II complexes causes their NLO responses to surpass those of their Ru-II counterparts upon changing the solvent medium.
• Crystal structures and visible-light excited photoluminescence of N-methyl-4,4′-bipyridinium chloride and its Zn(II) and Cd(II) complexes
  作者：Chen Yang、Ming-Sheng Wang、Li-Zhen Cai、Xiao-Ming Jiang、Mei-Feng Wu、Guo-Cong Guo、Jin-Shun Huang

  DOI：10.1016/j.inoche.2010.05.020

  日期：2010.9

  A new approach has been used to synthesize MQ(+) ligand (MQ(+) = N-methyl-4,4'-bipyridinium) by the reaction of 4,4'-bipyridine and chloroacetic acid, and the structure of (MQ)Cl center dot H2O (1) was first determined. Three new complexes containing MQ(+), (MQ)CdI3 (2). (MQ)ZnI3 (3), and [(MQ)znCl(1.53)I(1.47)](2)(MQ) ZnCl1.68I1.32 (4). were successfully obtained via a solution or hydrothermal method by reaction of MI2 (M = Cd, Zn) with 1, and each of which exhibits an isolated structure, with each metal atom coordinated by one MQ ligand and three terminal halogen atoms. Compounds 1-4 all display photoluminescence in the visible region under visible-light excitation, and the origins of the emissions have been assigned to ILCT for 1 and the combination of ILCT and LLCT for 2-4. (C) 2010 Elsevier B.V. All rights reserved.