dipyrido<1,2-a:1',2'-e>-1,3,4,6-tetraazapentalene | 104716-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]吡啶
• 英文名称: dipyrido<1,2-a:1',2'-e>-1,3,4,6-tetraazapentalene
• 英文别名: dipyrido<1,2-a:1'2'-e>1,3,4,6-tetraazapentalene；pyrido[2'',1'':2',3']imidazo[4',5':4,5]imidazo[1,2-a]pyridine；dipyrido[1,2-a:1'2'-e]1,3,4,6-tetraazapentalene；2,8,10,16-tetrazatetracyclo[7.7.0.02,7.010,15]hexadeca-1(9),3,5,7,11,13,15-heptaene
• CAS: 104716-50-9
• 化学式: C₁₂H₈N₄
• 分子量: 208.222
• InChiKey: ANMGHQUYEIIMOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-异氰基吡啶 以 1,4-二氧六环 为溶剂， 以63%的产率得到dipyrido<1,2-a:1',2'-e>-1,3,4,6-tetraazapentalene
  参考文献：
  名称：

  Dimerization of 2-pyridylisonitriles produces π-extended fused heteroarenes useful as highly selective colorimetric and optical probes for copper ion

  摘要：

  A very simple synthesis of pyrido[2 '',1 '':2',3']imidazo[4',5':4,5]imidazo[1,2-a]Pyridines 2 was achieved from the dimerization of 2-pyridylisonitriles. The optical responses of these pi-extended fused heteroarenes to a series of metal ions were investigated by means of UV-visible absorption spectrum in acetonitrile. It was found that most of compounds 2 selectively responded to Cu2+, and the limit of detection was about 3.5 x 10(-7) M when using the best probe, 3,9-dimethylpyrido[2",1":2',3']imidazo[4',5':4,5] imidazol1,2-a]pyridine 2d. Meanwhile some compounds 2 specifically showed a color change from colorless to red or yellow when they are exposed to copper ion in acetonitrile, whereas other transitional, alkali and alkaline earth metal ions could not induce a color change. This work not only established a direct access to pi-extended fused heteroarenes, but also supplied novel sensitive and selective colorimetric and optical probes for copper ion. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.096

文献信息

• Fluorescent heterocyclic systems: syntheses, structures, and physicochemical properties of dipyrido-substituted 1,3,4,6-tetraazapentalenes
  作者：Michael P. Groziak、Scott R. Wilson、Gary L. Clauson、Nelson J. Leonard

  DOI：10.1021/ja00285a020

  日期：1986.12
• Dimerization of 2-pyridylisonitriles produces π-extended fused heteroarenes useful as highly selective colorimetric and optical probes for copper ion
  作者：Na Shao、Guang-Xian Pang、Xiao-Rong Wang、Rui-Juan Wu、Ying Cheng

  DOI：10.1016/j.tet.2010.06.096

  日期：2010.9

  A very simple synthesis of pyrido[2 '',1 '':2',3']imidazo[4',5':4,5]imidazo[1,2-a]Pyridines 2 was achieved from the dimerization of 2-pyridylisonitriles. The optical responses of these pi-extended fused heteroarenes to a series of metal ions were investigated by means of UV-visible absorption spectrum in acetonitrile. It was found that most of compounds 2 selectively responded to Cu2+, and the limit of detection was about 3.5 x 10(-7) M when using the best probe, 3,9-dimethylpyrido[2",1":2',3']imidazo[4',5':4,5] imidazol1,2-a]pyridine 2d. Meanwhile some compounds 2 specifically showed a color change from colorless to red or yellow when they are exposed to copper ion in acetonitrile, whereas other transitional, alkali and alkaline earth metal ions could not induce a color change. This work not only established a direct access to pi-extended fused heteroarenes, but also supplied novel sensitive and selective colorimetric and optical probes for copper ion. (C) 2010 Elsevier Ltd. All rights reserved.

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