cis-2-[4'-(dimethylamino)styryl]benzothiazole | 1283177-49-0

• 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: cis-2-[4'-(dimethylamino)styryl]benzothiazole
• 英文别名: 4-[(Z)-2-(1,3-benzothiazol-2-yl)ethenyl]-N,N-dimethylaniline
• CAS: 1283177-49-0
• 化学式: C₁₇H₁₆N₂S
• 分子量: 280.393
• InChiKey: MVMOMSLTZMMLJR-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-[(1E)-2-(2-benzothiazolyl)ethenyl]-N,N-dimethylbenzenamine 以 氯仿 为溶剂， 生成 cis-2-[4'-(dimethylamino)styryl]benzothiazole
  参考文献：
  名称：

  Photoisomerization oftrans-2-[4′-(Dimethylamino)styryl]benzothiazole

  摘要：

  AbstractPhotoreaction of trans‐2‐[4′‐(dimethylamino)styryl]benzothiazole (t‐DMASBT) under direct irradiation has been investigated in dioxane, chloroform, methanol and glycerol to understand the mechanism of photoisomerization. Contrary to an earlier report, isomerization takes place in all these solvents including glycerol. The results show that restriction on photoisomerization leads to the increase in fluorescence quantum yield in glycerol. The results are consistent with the theoretically simulated potential energy surface reported earlier using time‐dependent density functional theory (TDDFT) calculations. DFT calculations on cis isomers under isolated condition have suggested that cis‐B conformer is more stable than cis‐A conformer due to hydrogen‐bonding interaction. In the ground state, cis‐DMASBT is predominantly present as cis‐B. The fluorescence spectra of the irradiated t‐DMASBT suggested that photoisomerization follows not the adiabatic path as proposed by Saha et al., but the nonadiabatic path.

  DOI：

  10.1111/j.1751-1097.2012.01227.x

文献信息

• Photoisomerization of<i>trans</i>-2-[4′-(Dimethylamino)styryl]benzothiazole
  作者：Anasuya Mishra、Arumugam Thangamani、Soumya Chatterjee、Francis A. S. Chipem、Govindarajan Krishnamoorthy

  DOI：10.1111/j.1751-1097.2012.01227.x

  日期：2013.1

  AbstractPhotoreaction of trans‐2‐[4′‐(dimethylamino)styryl]benzothiazole (t‐DMASBT) under direct irradiation has been investigated in dioxane, chloroform, methanol and glycerol to understand the mechanism of photoisomerization. Contrary to an earlier report, isomerization takes place in all these solvents including glycerol. The results show that restriction on photoisomerization leads to the increase in fluorescence quantum yield in glycerol. The results are consistent with the theoretically simulated potential energy surface reported earlier using time‐dependent density functional theory (TDDFT) calculations. DFT calculations on cis isomers under isolated condition have suggested that cis‐B conformer is more stable than cis‐A conformer due to hydrogen‐bonding interaction. In the ground state, cis‐DMASBT is predominantly present as cis‐B. The fluorescence spectra of the irradiated t‐DMASBT suggested that photoisomerization follows not the adiabatic path as proposed by Saha et al., but the nonadiabatic path.