3-Methyl-2-[(Z)-2-phenylethenyl]-1,3-benzothiazol-3-ium iodide | 1592-72-9

• 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: 3-Methyl-2-[(Z)-2-phenylethenyl]-1,3-benzothiazol-3-ium iodide
• 英文别名: 3-methyl-2-[(Z)-2-phenylethenyl]-1,3-benzothiazol-3-ium;iodide
• CAS: 1592-72-9；118357-46-3
• 化学式: C₁₆H₁₄NS*I
• 分子量: 379.264
• InChiKey: MRQHEGLZGYQIMP-AFEZEDKISA-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：

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

  Photophysics, photochemistry and thermal stability of diarylethene-containing benzothiazolium species

  摘要：

  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.

  DOI：

  10.1016/j.jphotochem.2014.12.015
• 作为产物：
  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

文献信息

• 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：——
• Fast (hetero)aryl-benzothiazolium ethenes photoswitches activated by visible-light at room temperature
  作者：Paulo J. Coelho、M. Cidália R. Castro、M. Manuela M. Raposo

  DOI：10.1016/j.dyepig.2015.02.015

  日期：2015.6

  A series of novel photochromic cationic stilbenes dyes bearing different aromatic systems were easily synthesized from (hetero)aromatic aldehydes. The photoisomerization of the double bond can be achieved through irradiation with ultraviolet or visible light, for few seconds, leading to the Z isomers that return much faster to the initial state than common stilbenes. Benzothiazolium dyes with electron

  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。
• 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.