6-dimethylamino-2-(4-formylphenyl)benzothiazole

• 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: 6-dimethylamino-2-(4-formylphenyl)benzothiazole
• 英文别名: 4-(6-(Dimethylamino)benzo[D]thiazol-2-YL)benzaldehyde；4-[6-(dimethylamino)-1,3-benzothiazol-2-yl]benzaldehyde
• 化学式: C₁₆H₁₄N₂OS
• 分子量: 282.366
• InChiKey: IILRREZVFUDZDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-茚满二酮 、 6-dimethylamino-2-(4-formylphenyl)benzothiazole 在 吡啶 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 以53%的产率得到2-[[4-[6-(Dimethylamino)-1,3-benzothiazol-2-yl]phenyl]methylidene]indene-1,3-dione
  参考文献：
  名称：

  Structure-fluorescence relationship of push-pull 2-phenylbenzothiazole derivatives designed based on the firefly light-emitter

  摘要：

  6-Dimethylamino-2-phenylbenzothiazole (1a) mimicking the firefly oxyluciferin structure and the derivatives with an electron-withdrawing substituent on the phenyl group were prepared, and their fluorescence properties were investigated in various solvents. la showed solvatochromic fluorescence with good fluorescence quantum yields (Phi(f) >0.8). The introduction of an electron-withdrawing group led to a red-shift of the emission maximum. In particular, the derivatives with the 2,2-dicyanoethenyl and (1,3-dihydro-1,3-dioxo-2H-inden-2-ylidene)methyl groups showed near-infrared fluorescence in chloroform. In addition, the derivative with the phenylimine moiety showed efficient solid-state fluorescence, resulted from a molecular arrangement inhibiting intermolecular interactions for quenching the fluorescence state in crystals. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.02.075
• 作为产物：
  描述：

  2-chloro-6-dimethylamino-benzothiazole 、 4-甲酰基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到6-dimethylamino-2-(4-formylphenyl)benzothiazole
  参考文献：
  名称：

  Structure-fluorescence relationship of push-pull 2-phenylbenzothiazole derivatives designed based on the firefly light-emitter

  摘要：

  6-Dimethylamino-2-phenylbenzothiazole (1a) mimicking the firefly oxyluciferin structure and the derivatives with an electron-withdrawing substituent on the phenyl group were prepared, and their fluorescence properties were investigated in various solvents. la showed solvatochromic fluorescence with good fluorescence quantum yields (Phi(f) >0.8). The introduction of an electron-withdrawing group led to a red-shift of the emission maximum. In particular, the derivatives with the 2,2-dicyanoethenyl and (1,3-dihydro-1,3-dioxo-2H-inden-2-ylidene)methyl groups showed near-infrared fluorescence in chloroform. In addition, the derivative with the phenylimine moiety showed efficient solid-state fluorescence, resulted from a molecular arrangement inhibiting intermolecular interactions for quenching the fluorescence state in crystals. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.02.075

文献信息

• Structure-fluorescence relationship of push-pull 2-phenylbenzothiazole derivatives designed based on the firefly light-emitter
  作者：Tomoya Fujikawa、Takuya Uehara、Minoru Yamaji、Takuya Kanetomo、Takayuki Ishida、Shojiro Maki、Takashi Hirano

  DOI：10.1016/j.tetlet.2018.02.075

  日期：2018.4

  6-Dimethylamino-2-phenylbenzothiazole (1a) mimicking the firefly oxyluciferin structure and the derivatives with an electron-withdrawing substituent on the phenyl group were prepared, and their fluorescence properties were investigated in various solvents. la showed solvatochromic fluorescence with good fluorescence quantum yields (Phi(f) >0.8). The introduction of an electron-withdrawing group led to a red-shift of the emission maximum. In particular, the derivatives with the 2,2-dicyanoethenyl and (1,3-dihydro-1,3-dioxo-2H-inden-2-ylidene)methyl groups showed near-infrared fluorescence in chloroform. In addition, the derivative with the phenylimine moiety showed efficient solid-state fluorescence, resulted from a molecular arrangement inhibiting intermolecular interactions for quenching the fluorescence state in crystals. (C) 2018 Elsevier Ltd. All rights reserved.