1-ethyl-4-(4-pyridyl)pyridinium iodide | 63962-86-7

• 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: 1-ethyl-4-(4-pyridyl)pyridinium iodide
• 英文别名: 1-Ethyl-4-pyridin-4-ylpyridin-1-ium;iodide
• CAS: 63962-86-7
• 化学式: C₁₂H₁₃N₂*I
• 分子量: 312.153
• InChiKey: FXRXLHRKWHIJBT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.94
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  16.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ethyl-4-(4-pyridyl)pyridinium iodide 在 sodium tetrahydroborate 、 potassium permanganate 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.75h， 生成 3,4-dihydroxy-1-ethyl-2-oxo-4-(γ-pyridyl)piperidine
  参考文献：
  名称：

  Oxidative reactions of azines

  摘要：

  Oxidative coupling of 1-alkyl(benzyl)-4-(gamma-Pyridyl)-1,2,5,6-tetrahydropyridines with acetone in the presence of KMnO4 follows two pathways and yields both 1-R-2-(acetylmethylene)tetrahydropyridines and 1-R-3,4-dihydroxypiperidin-2-ones. When acetonitrile is used instead of acetone, the reaction under similar conditions occurs as selective ketodihydroxylation of the starting piperideines yielding 1-R-3,4-dihydroxy-4(gamma-Pyridyl)piperidin-2-ones . The molecular and crystal structures of one of these products (R = Et) was studied by X-ray diffraction analysis.

  DOI：

  10.1007/bf02503786
• 作为产物：
  描述：

  4,4'-联吡啶 、 碘乙烷 以 乙醚 为溶剂， 反应 72.0h， 以10%的产率得到1-ethyl-4-(4-pyridyl)pyridinium iodide
  参考文献：
  名称：

  共价修饰碳上的亲核和亲电置换：在接枝玻璃碳电极上引入4,4'-联吡啶

  摘要：

  通过涉及1-乙基-或1-苄基-4-（4'-吡啶基）吡啶鎓的亲核取代反应，将4,4'-联吡啶鎓（即，紫精）固定在4-（氯甲基）苯基接枝的玻璃碳电极上。这些受表面限制的过程需要大约5天的反应时间才能在室温下在水溶液中完成。首先通过与以下试剂反应，分两步进行等效修饰，证明了所描述方法的适用性4,4'-联吡啶，然后对可用的进行四元化 氮以获得紫精功能，即表面在取代反应中充当亲核试剂。但是，发现季铵化步骤可能会引入苄基 但不是 乙基。共价修饰的电极对于反复的电化学扫描相当稳定乙腈在以2 V s -1的扫描速率进行100次扫描后，观察到的电活性降低了25％。根据紫精部分的电化学反应确定覆盖度为约3×10 -10 mol cm -2。此外循环伏安法，通过以下方法证明了紫精的存在 X射线光电子能谱 和 飞行时间二次离子质谱。通过后一种技术获得的扫描图像（500×500 µm 2）表明分子均匀地分布在整个表面上。扫描隧道显微镜

  DOI：

  10.1039/b415623d

文献信息

• Bromination of N -phenyloxypropyl- N ′-ethyl-4,4′-bipyridium in cucurbit[8]uril molecular reactor
  作者：Tian-Tian Li、Lan-Lan Wen、Hai-Long Ji、Feng-Yu Liu、Shi-Guo Sun

  DOI：10.1016/j.cclet.2016.10.004

  日期：2017.2

  Abstract CB[n] (n = 6–8) is a family of synthetic macrocyclic host molecules composed of n glycoluril units, which can be employed as molecular reactor. N -Phenyloxypropyl- N ′-ethyl-4,4′-bipyridium ( 1 ) was designed to form a host–guest inclusion complex with CB[n] (n = 6–8), subsequently, the bromination reaction of 1 and its corresponding inclusion complexes was investigated in this work. In the

  摘要CB [n]（n = 6-8）是由n个甘脲单元组成的合成大环主体分子家族，可以用作分子反应器。N-苯氧丙基-N'-乙基-4,4'-联吡啶（1）设计为与CB [n]（n = 6-8）形成主体-客体包合配合物，随后进行1及其溴化反应在这项工作中研究了相应的包合物。在1 / CB [8]的情况下，折叠包含模式非常有助于通过分子内电荷转移（ICT）完全获得1-硼化产物，而CB [8]可以为1提供安全的溴化环境。
• O-atom effect on the dynamic balance between redox-induced viologen derivative radical and its dimer modulated by cucurbit[8]uril
  作者：Xinwei Song、Fengyu Liu、Shiguo Sun、Jingnan Cui、Jiangli Fan、Fengling Song、Xiaojun Peng

  DOI：10.1080/10610278.2013.792338

  日期：2013.7.1

  which can form stable 1:1 inclusion complexes with cucurbit[8]uril (CB[8]) in aqueous solution. The one-electron-reduced viologen radical cations and its dimerisation encapsulated into CB[8] were studied spectroscopically. The monomer–dimer dynamic balance would exist in the molecules containing O-atom, while the molecules without O-atom retain the form of radical monomer in CB[8] cavity. The result demonstrated

  合成了一系列紫精衍生物，在水溶液中可与葫芦[8]脲(CB[8])形成稳定的1:1包合物。通过光谱研究了单电子还原紫罗碱自由基阳离子及其封装在 CB 中的二聚化 [8]。单体-二聚体动态平衡存在于含O原子的分子中，而不含O原子的分子在CB[8]腔中保留自由基单体的形式。结果表明，CB可以调节这些配合物的自由基单体和二聚体的动态平衡[8]。
• Two new Co(II) coordination polymers based on redox-active ligands: Structure, Chromism and Magnetism
  作者：Wen-Jing Xu、Kun-Peng Chen、Yue Zhang、Yue Ma、Quan-Wen Li、Qing-Lun Wang

  DOI：10.1016/j.molstruc.2021.129948

  日期：2021.5

  By utilizing redox-active ligands [monoquaternized 4,4′-bipyridines (monoquats) and naphthalene diimide derivatives] and dicyanamide (dca) bridges, two new Co(II) complexes, [Co(dca)2(DPNDI)]n⋅2nDMF⋅nH2O (1) and [Co(EQ)2(dca)2]nI2n⋅4nH2O (2), have been synthesized (DPNDI = N,N'-di(3-pyridyl)-1,4,5,8-naphthalene tetracarboxydiimide, EQI = 1-ethyl-4-(4-pyridyl) pyridinium iodide). Complex 1 is a 2D network

  通过利用氧化还原活性的配体[monoquaternized 4,4'-联吡啶（monoquats）和萘二酰亚胺衍生物]和二氰胺（DCA）桥梁，两个新的Co（II）络合物，[CO（DCA）2（DPNDI）] Ñ ⋅2nDMF ⋅nH 2 O（1）和[CO（EQ）2（DCA）2 ] ñ我的2n ⋅4nH 2 O（2），已经合成了（DPNDI =  ñ，N'-二（3-吡啶基）-1， 4,5,8-萘四羧二酰亚胺，EQI = 1-乙基-4-（4-吡啶基）碘化吡啶鎓）。配合物1是2D网络，其中[Co（dca）2 ] n的1D链通过DPNDI配体连接形成2D层。在复杂的2中，[Co（EQ）2（dca）的1D链2 ] n垂直交叉。有趣的是，配合物1是光致变色的，而配合物2是光致变色和热致变色的。此外，还研究了它们的磁性能。
• Redox-induced partner radical formation and its dynamic balance with radical dimer in cucurbit[8]uril
  作者：Tongyan Zhang、Shiguo Sun、Fengyu Liu、Jiangli Fan、Yi Pang、Licheng Sun、Xiaojun Peng

  DOI：10.1039/b916591f

  日期：——

  1 : 1 inclusion complex with CB[8] in aqueous solution, in which the hydroxyphenol (HP) moiety is back-folded and inserted together with the viologen moiety into the cavity of CB[8]. When the ethyl viologen dication (EV2+) in 1 is reduced, chemically or electrochemically, an intramolecular partner radical (EV+˙-HP)/CB[8] can be detected, meanwhile, a dynamic balance between the partner radical and the

  N-（4-羟基-苯氧基乙基）-N'-乙基-4,4'-联吡啶鎓（1）可以与以下物质形成稳定的1：1包合物CB [8] 在水溶液中 羟基苯酚 （HP）部分向后折叠，并与紫精部分一起插入到 CB [8]。当以化学或电化学方式还原1中的乙基紫精指示剂（EV 2+）时，分子内伙伴基团（电动车+生命值）/CB [8] 同时可以检测到伴侣基团与分子间基团二聚体之间的动态平衡 （EV + ˙-HP）2/CB [8] 可以观察到。
• Impact of Redox-Active Polymer Molecular Weight on the Electrochemical Properties and Transport Across Porous Separators in Nonaqueous Solvents
  作者：Gavvalapalli Nagarjuna、Jingshu Hui、Kevin J. Cheng、Timothy Lichtenstein、Mei Shen、Jeffrey S. Moore、Joaquín Rodríguez-López

  DOI：10.1021/ja508482e

  日期：2014.11.19

  Enhancing the ionic conductivity across the electrolyte separator in nonaqueous redox flow batteries (NRFBs) is essential for improving their performance and enabling their widespread utilization. Separating redox-active species by size exclusion without greatly impeding the transport of supporting electrolyte is a potentially powerful alternative to the use of poorly performing ion-exchange this has not been explored due the lack of membranes. However, strategy possibly to suitable redox-active species that are easily varied in size, remain highly soluble, and exhibit good electrochemical properties. Here we report the synthesis, electrochemical characterization, and transport properties of redox-active poly(vinylbenzyl ethylviologen) (RAPs) with molecular weights between 21 and 318 kDa. The RAPs reported here show very good solubility (up to at least 2.0 M) in acetonitrile and propylene carbonate. Ultramicroelectrode voltammetry reveals facile electron transfer with E-1/2 similar to -0.7 V vs Ag/Ag+(0.1 M) for the viologen 2+/+ reduction at concentrations as high as 1.0 M in acetonitrile. Controlled potential bulk electrolysis indicates that 94-99% of the nominal charge on different RAPs is accessible and that the electrolysis products are stable upon cycling. The dependence of the diffusion coefficient on molecular weight suggests the adequacy of the Stokes Einstein formalism to describe RAPs. The size-selective transport properties of LiBF4 and RAPs across commercial off-the-shelf (COTS) separators such as Celgard 2400 and Celgard 2325 were tested. COTS porous separators show ca. 70 times higher selectivity for charge balancing ions (Li+BF4-) compared to high molecular weight RAPs. RAPs rejection across these separators showed a strong dependence on polymer molecular weight as well as the pore size; the rejection increased with both increasing polymer molecular weight and reduction in pore size. Significant rejection was observed even for r(poly)/r(pore) (polymer solvodynamic size relative to pore size) values as low as 0.3. The high concentration attainable (>2.0 M) for RAPs in common nonaqueous battery solvents, their electrochemical and chemical reversibility, and their hindered transport across porous separators make them attractive materials for nonaqueous redox flow batteries based on the enabling concept of size-selectivity.