(E)-2-styryl-3-methylbenzo[d]thiazol-3-ium iodide | 118357-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (E)-2-styryl-3-methylbenzo[d]thiazol-3-ium iodide
• 英文别名: (E)-3-methyl-2-styrylbenzo[d]thiazol-3-ium iodide；3-methyl-2-[(E)-2-phenylethenyl]-1,3-benzothiazol-3-ium;iodide
• CAS: 118357-46-3
• 化学式: C₁₆H₁₄NS*I
• 分子量: 379.264
• InChiKey: MRQHEGLZGYQIMP-CALJPSDSSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-styryl-3-methylbenzo[d]thiazol-3-ium iodide 以 乙腈 为溶剂， 生成 3-Methyl-2-[(Z)-2-phenylethenyl]-1,3-benzothiazol-3-ium iodide
  参考文献：
  名称：

  室温下可见光激活的快速（杂）芳基-苯并噻唑鎓乙烯光开关

  摘要：

  易于从（杂）芳族醛中合成出一系列带有不同芳族体系的新型光致变色阳离子对苯二酚染料。双键的光异构化可以通过用紫外线或可见光照射几秒钟来实现，从而导致Z异构体比普通的对苯二甲酸酯更快地返回初始状态。具有给电子取代基的苯并噻唑鎓染料表现出非常快速的热逆反应（<1 s）。吡咯-苯并噻唑鎓染料在不同的溶剂（包括水）中显示出更高的Z异构体寿命（0.45–7.1分钟）。阳离子二芳基乙烯可以在EZ之间切换 在室温下，使用可见光在几分钟内即可进入可见光状态，可见光谱会发生显着变化。

  DOI：

  10.1016/j.dyepig.2015.02.015
• 作为产物：
  描述：

  2-甲基苯并噻唑 在 哌啶 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.0h， 生成 (E)-2-styryl-3-methylbenzo[d]thiazol-3-ium iodide
  参考文献：
  名称：

  室温下可见光激活的快速（杂）芳基-苯并噻唑鎓乙烯光开关

  摘要：

  易于从（杂）芳族醛中合成出一系列带有不同芳族体系的新型光致变色阳离子对苯二酚染料。双键的光异构化可以通过用紫外线或可见光照射几秒钟来实现，从而导致Z异构体比普通的对苯二甲酸酯更快地返回初始状态。具有给电子取代基的苯并噻唑鎓染料表现出非常快速的热逆反应（<1 s）。吡咯-苯并噻唑鎓染料在不同的溶剂（包括水）中显示出更高的Z异构体寿命（0.45–7.1分钟）。阳离子二芳基乙烯可以在EZ之间切换 在室温下，使用可见光在几分钟内即可进入可见光状态，可见光谱会发生显着变化。

  DOI：

  10.1016/j.dyepig.2015.02.015

文献信息

• Synthesis and Study of Novel Benzothiazole Derivatives with Potential Nonlinear Optical Properties
  作者：Ivica Sigmundová、Pavol Zahradník、Dušan Loos

  DOI：10.1135/cccc20071069

  日期：——

  The synthesis of new benzothiazole push-pull systems as candidates for NLO-phores is described. Spectral (UV/VIS and solvatochromic) and theoretical studies (electronic properties based on semiempirical AM1 and PM3 methods) of the prepared compounds were carried out. The structure and physico-chemical parameters affecting the push-pull character and intramolecular charge transfer (ICT) of the studied compounds have been investigated and compounds with enhanced hyperpolarizability β have been predicted. The benzothiazolium salts were found to be much more effective NLO-phores in comparison with the corresponding neutral benzothiazoles. The 4-NPh₂ group is the most effective donor. The extension of conjugated bridge improves the studied NLO characteristics. An additional acceptor group bonded to the heterocycle causes a red shift of λ_max but does not increase hyperpolarizability.

  描述了合成新的苯并噻唑推-拉系统作为NLO荧光团的候选物。对所制备化合物进行了光谱（UV/VIS和溶剂致色性）和理论研究（基于半经验AM1和PM3方法的电子性质）。研究了影响推-拉性质和分子内电荷转移（ICT）的结构和物理化学参数，并预测了具有增强高极化率β的化合物。与相应的中性苯并噻唑相比，苯并噻唑盐在NLO荧光团中表现出更高的效果。4-NPh2基团是最有效的给体。共轭桥的延伸改善了研究的NLO特性。附加的受体基团与杂环相结合导致了λmax的红移，但并不增加高极化率。
• Base‐Mediated Synthesis of 1,3‐Diazaphenothiazines from 2‐Methylbenzothiazoliums, Aryl Aldehydes and Amidines
  作者：Baihui Liang、Haiyin Deng、Shengting Xu、Jie Huang、Jingyu Liu、Xiangya Cai、Tian‐Xiang Chen、Xiuwen Chen、Zhongzhi Zhu

  DOI：10.1002/adsc.202301015

  日期：2024.1.9

  Conflict of interest There are no conflicts to declare.

  利益冲突 没有需要声明的冲突。
• Photophysics, photochemistry and thermal stability of diarylethene-containing benzothiazolium species
  作者：Morad M. El-Hendawy、Tarek A. Fayed、Mohamed K. Awad、Niall J. English、Safaa Eldin H. Etaiw、Ahmed B. Zaki

  DOI：10.1016/j.jphotochem.2014.12.015

  日期：2015.3

  The photophysics, photochemistry and thermal stability of four 1-atyl-2-(N-methyl-2-benzothiazolium) ethene iodides (aryl: phenyl, 1-naphthyl, 9-phenanthryl and 9-anthryl) were studied. Although the absorption spectra are found to be hypsochromic-shifted, fluorescence spectra are bathochromic-shifted. The dipole moment in the relaxed excited state was found to be larger than that in the ground state. To investigate effects of N-methylation and the aryl-ring size, a detailed comparison was made between those in the present work (of charged compounds) and previous studies of their neutral analogues, with computed electron affinity and ionisation potentials serving to rationalise the experimentally observed bathochromic shifts in absorption and emission spectra. The kinetics of thermal isomerisation depend strongly on the nature of the aryl moiety and solvent; the larger the aryl ring, the slower the rate of isomerisation. The fastest isomerisation process was found to take place in MeOH. The anthryl derivative did not isomerize either by light- or heat-exposure, due to high energy barriers of rotation around the ethenic bond. Based on the significant blue-shift of the Z-isomer absorption maximum relative to that of the E-isomer, and the high percentage of Z-isomers in the photostationary state, these compounds may serve as potential promising candidates for optical data-storage applications. (C) 2015 Elsevier B.V. All rights reserved.
• GAPLOVSKY, A.;CHABRECEK, P.;SUTORIS, V., CHEM. PAP., 42,(1988) N 1, 67-71
  作者：GAPLOVSKY, A.、CHABRECEK, P.、SUTORIS, V.

  DOI：——

  日期：——
• Design and Synthesis of Novel c-di-GMP G-Quadruplex Inducers as Bacterial Biofilm Inhibitors
  作者：Teng-Fei Xuan、Zi-Qiang Wang、Jun Liu、Hai-Tao Yu、Qian-Wen Lin、Wei-Min Chen、Jing Lin

  DOI：10.1021/acs.jmedchem.1c00465

  日期：2021.8.12

  c-di-GMP-mediated biofilm regulatory pathway, was proposed in this study. In this new strategy, a series of novel c-di-GMP G-quadruplex inducers were designed and synthesized for development of therapeutic biofilm inhibitors. Compound 5h exhibited favorable c-di-GMP G-quadruplex-inducing activity and 62.18 ± 6.76% biofilm inhibitory activity at 1.25 μM without any DNA intercalation effect. Moreover, the

  临床病原体形成的生物膜通常会导致慢性和复发性抗生素耐药性感染。高细胞水平的环二鸟苷酸 (c-di-GMP) 是一种无处不在的细菌二级信使，已被证明与病原体的固着生物膜生活方式有关。本研究提出了一种有前景的抗生物膜策略，包括诱导 c-di-GMP 形成功能失调的 G-四链体，从而阻断 c-di-GMP 介导的生物膜调节途径。在这一新策略中，设计并合成了一系列新型 c-di-GMP G-四联体诱导剂，用于开发治疗性生物膜抑制剂。复合5h在 1.25 μM 下表现出良好的 c-di-GMP G-四链体诱导活性和 62.18 ± 6.76% 的生物膜抑制活性，没有任何 DNA 嵌入效应。此外，5h在干扰 c-di-GMP 相关生物学功能方面的良好表现，包括细菌运动和细菌胞外多糖分泌，结合报告菌株和转录组分析结果证实了 c-di-GMP 信号相关的作用机制的5H。