4-methyl-1-octadecylpyridinium iodide | 70710-08-6

• 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: 4-methyl-1-octadecylpyridinium iodide
• 英文别名: 4-Methyl-1-octadecylpyridin-1-ium iodide；4-methyl-1-octadecylpyridin-1-ium;iodide
• CAS: 70710-08-6
• 化学式: C₂₄H₄₄N*I
• 分子量: 473.525
• InChiKey: MBZZPBIVCHFMGV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 、 4-methyl-1-octadecylpyridinium iodide 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (E)-Octadecyl-4-<2-(4-diethylaminophenyl)ethenyl>pyridinium iodide
  参考文献：
  名称：

  Langmuir–Blodgett film and second harmonic generation of a new type of amphiphilic non-linear optical bis-chromophore complex dye

  摘要：

  A bivalent zinc complex anion: bis(2-thione-1,3-dithiol-4,5-dimercapto)zinc, has been chosen to balance several non-linear optical (NLO) dye cations in the design and synthesis of a series of novel bis-chromophore complex dyes. The Langmuir film-forming properties of these new NLO complex dyes at the air/water interface, the stability and second-order non-linear optical properties of the monolayer and Langmuir-Blodgett multilayer films were investigated. Results show that both the film-forming properties and NLO coefficiencies were improved greatly when the zinc complex anion was incorporated into four types of NLO-active organic dyes.

  DOI：

  10.1039/ft9969202585
• 作为产物：
  描述：

  4-甲基吡啶 、 1-碘十八烷 以 乙醇 为溶剂， 以79 %的产率得到4-methyl-1-octadecylpyridinium iodide
  参考文献：
  名称：

  调节荧光探针的烷基链以选择性靶向活细胞中的细胞膜或线粒体

  摘要：

  活细胞中细胞膜和线粒体行为的可视化具有重要的生命科学价值，但由于缺乏理想的探针而具有挑战性。在这项工作中，报道了两种基于不同长度烷基链的新型荧光探针，用于选择性靶向活细胞的细胞膜或线粒体。探针CTM (1-Octadecyl-4-[9-ethyl-6-(diphenylamino)-9H-carbazol-3-yl] pyridinium) 在细胞中实现了细胞膜特异性染色。此外，探针CTM可以通过亚细胞迁移监测细胞膜损伤。一旦细胞膜受损，探针CTM就会作为信号报告分子迁移到线粒体中。此外，探针MTM(1-Dodecly-4-[9-ethyl-6-(diphenylamino)-9H-carbazol-3-yl] pyridinium) 具有相同骨架结构的较短烷基链穿透细胞膜并对线粒体表现出高亲和力。这项工作将提供一个有用的工具来可视化活细胞中细胞膜和线粒体的行为。

  DOI：

  10.1016/j.saa.2022.122280

文献信息

• Synthesis and mesophase behaviour of ionic liquid crystals
  作者：D. Ster、U. Baumeister、J. Lorenzo Chao、C. Tschierske、G. Israel

  DOI：10.1039/b705519f

  日期：——

  N-Alkyl-pyridinium derivatives 1–3 and N-alkyl-stilbazolium halides 4–6 with hydroxy, methoxy and hydrogen 4′-substituents and long non-branched alkyl chains (n = 14, 16, 18, 20, 22) were synthesized and characterized by polarizing microscopy, differential scanning calorimetry and X-ray measurements. The compounds exhibit liquid crystalline SmA phases when heated above their melting point. Phenyl substitution in the 3- and 4-position of the pyridinium ring causes a large tendency to decrease the clearing temperature in comparison to the 4-methyl substituted N-alkyl-pyridinium salts. By elongation of the pyridinium ring to the 4′-substituted stilbazolium unit the clearing points of the new compounds 4–6 increase drastically up to temperatures ≥200 °C in which partial decomposition of the compounds sets in. The length of the alkyl chains and the type of counter ions have large influences on the stability of the mesophase. Elongation of the alkyl chain length n increases the temperature range of the liquid crystalline phase. The counter ions increase the stability of the SmA phase in order Cl− > Br− > I− > BPh4−. When CH3–C6H5SO3− is introduced as an anion no liquid crystalline phase can be observed. UV/Vis measurements indicate the presence of a charge-transfer complex between the pyridinium cation and the iodide anion. Differences in the liquid crystalline behaviour of N-alkyl-4′-substituted stilbazolium halides 4–6 compared with N-alkyl-3- and -4-substituted-pyridinium derivatives 1–3 may be explained by additional intramolecular charge-transfer and resulting strong dipole–dipole interactions between stilbazolium compounds.

  合成并表征了具有羟基、甲氧基和氢的4′-取代基以及长的非分支烷基链（n = 14、16、18、20、22）的N-烷基吡啶鎓衍生物1–3和N-烷基斯替巴唑鎓卤化物4–6，采用了偏振显微镜、差示扫描量热法和X射线测量。化合物在加热至其熔点以上时表现出液晶SmA相。吡啶环3位和4位的苯基取代导致其清晰温度相较于4-甲基取代的N-烷基吡啶盐大幅降低。通过将吡啶环延伸至4′-取代的斯替巴唑鎓单元，新化合物4–6的清晰点大幅增加，达到≥200 °C的温度，在此温度下化合物开始部分分解。烷基链的长度和对离子的类型对中间相的稳定性有较大影响。烷基链长度n的延长增加了液晶相的温度范围。对离子按照Cl− > Br− > I− > BPh4−的顺序增加了SmA相的稳定性。当引入CH3–C6H5SO3−作为阴离子时，无法观察到液晶相。UV/Vis测量表明吡啶鎓阳离子和碘离子之间存在电荷转移复合物。与N-烷基-3和-4取代的吡啶衍生物1–3相比，N-烷基-4′-取代的斯替巴唑鎓卤化物4–6在液晶行为上的差异可以通过额外的分子内电荷转移和斯替巴唑化合物之间强的偶极-偶极相互作用来解释。
• A side-chain engineering strategy for constructing fluorescent dyes with direct and ultrafast self-delivery to living cells
  作者：Lifang Guo、Chuanya Li、Hai Shang、Ruoyao Zhang、Xuechen Li、Qing Lu、Xiao Cheng、Zhiqiang Liu、Jing Zhi Sun、Xiaoqiang Yu

  DOI：10.1039/c9sc05875c

  日期：——

  A side-chain engineering strategy can dramatically improve dye delivery by fine-tuning the adsorption and desorption abilities of the transmembrane process, enabling ultralow loading bioimaging and deep tissue penetration.

  通过侧链工程策略，可以通过微调跨膜过程的吸附和脱附能力，显著改善染料的输送，从而实现超低负载生物成像和深层组织穿透。
• A tunable detection range of ion-selective nano-optodes by controlling solvatochromic dye transducer lipophilicity
  作者：Lu Wang、Eric Bakker

  DOI：10.1039/c9cc06729a

  日期：——

  solvatochromic dye (SD) transducers for use in ion-selective emulsified optical sensors are introduced and characterized. They share the same chromophore group, (E)-4-(4-(dimethylamino)styryl)pyridinium, but vary in their lipophilicities by grafted alkyl or ethoxy groups. The calibration curve is found to shift by a total of 2.7 orders of magnitude with the lipophilicity of the SD.

  介绍并表征了一系列用于离子选择乳化光学传感器的离子型溶剂化变色染料（SD）传感器。它们具有相同的生色基团，（E）-4-（4-（二甲基氨基）苯乙烯基）吡啶鎓，但它们的亲脂性因接枝的烷基或乙氧基而异。发现该标定曲线随着SD的亲脂性总共移动了2.7个数量级。
• Electroactive compounds, compositions and devices and methods of making the same
  申请人：ATOCHEM NORTH AMERICA, INC.

  公开号：EP0491364A2

  公开（公告）日：1992-06-24

  The present invention relates to electroactive compounds capable of undergoing a change in light absorption and refraction due to an applied electric field and a permanent change in refraction due to exposure to predetermined bands of optical radiation. The present invention also relates to electroactive compositions containing such electroactive compounds, electrooptical components comprised of such electroactive compositions and electrooptical devices

  本发明涉及能够因外加电场而改变光吸收和折射以及因暴露于预定波段的光辐射而永久改变折射的电活性化合物。本发明还涉及含有这种电活性化合物的电活性组合物、由这种电活性组合物组成的光电元件和光电设备。
• 一种联苯吡啶盐类化合物及其制备方法和作为荧光探针在检测微囊藻毒素中的应用
  申请人：云南大学

  公开号：CN116730910A

  公开（公告）日：2023-09-12

  本发明属于生态毒理研究技术领域，具体涉及一种联苯吡啶盐类化合物及其制备方法和作为荧光探针在检测微囊藻毒素(MC‑LR)中的应用。本发明提供的联苯吡啶盐类化合物，具有式I所示结构。本发明提供的式I所示结构联苯吡啶盐类化合物在微囊藻毒素存在的条件下，能够凭借分子结构中线型结构，通过氢键相互作用与微囊藻毒素的环状结构相互嵌合，从而改变式I所示结构联苯吡啶盐类化合物自身的光谱性质，表现出具有较强的荧光响应，从而通过荧光强度变化实现对水相中MC‑LR的检测；同时，采用本发明提供的式I所示结构的联苯吡啶盐类化合物18BDQ能够实现对MC‑LR进行特异性检测，且操作方法简单，具有广阔的应用前景。