3-Pyridin-2-ylbenzo[g]quinoxaline-5,10-dione | 327627-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Pyridin-2-ylbenzo[g]quinoxaline-5,10-dione
• CAS: 327627-11-2
• 化学式: C₁₇H₉N₃O₂
• 分子量: 287.277
• InChiKey: ZOGMJEQGMURZJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Pyridin-2-ylbenzo[g]quinoxaline-5,10-dione 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 9.0h， 生成 1-methyl-2-{5,10-bis(dicyanomethylidene)naphtho[2,3-b]pyrazin-2-yl}pyridinium triflate
  参考文献：
  名称：

  Pyrazino-tetracyanonaphthoquinodimethanes: sterically deformed electron acceptors affording zwitterionic radicals

  摘要：

  The X-ray analyses of the title electron acceptors (1) revealed their butterfly-shaped deformed geometry, which is not affected by the pyridyl group attached at 2-position of the pyrazino-TCNNQ skeleton. Small differences between the first and second reduction potentials (ca. 0.1 V) in pyrazino-TCNNQs show that their anion radicals (1(-.)) are prone to disproportionate into the neutral (1) and dianionic (1(2-)) species. The thermodynamically unstable anion radical species based on the pyrazino-TCNNQ skeleton could be isolated as inner salts upon electrochemical reduction of the derivatives having an N-methylpyridinium moiety at 2-position (2(+)). The zwitterionic open-shell species (2) constitute a novel class of radicals that exhibit semiconducting behavior as a single component thanks to the high electrochemical amphotericity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.005
• 作为产物：
  描述：

  2,3-二氨基萘-1,4-二酮 、 2-溴-1-(2-吡啶基)-1-乙酮氢溴酸 以 二甲基亚砜 为溶剂， 反应 3.0h， 以30%的产率得到3-Pyridin-2-ylbenzo[g]quinoxaline-5,10-dione
  参考文献：
  名称：

  Single-Component Organic Semiconductors Based on Novel Radicals that Exhibit Electrochemical Amphotericity:  Preparation, Crystal Structures, and Solid-State Properties of N,N‘-Dicyanopyrazinonaphthoquinodiiminides Substituted with an N-Alkylpyridinium Unit

  摘要：

  N,N'-Dicyanonaphthoquinodiimines fused with a pyrazine ring 1 were prepared from the corresponding quinones 4. The new accepters 1 have a planar pi -system and undergo reversible two-stage 1e-reduction. Quaternization of the pyridyl substituent in 1d-f gave pyridinium derivatives 2d(+), 2e(+), and R-3(+), respectively, which are stronger accepters that undergo three-stage le-reduction. Upon electrochemical. reduction of these cations, novel radicals 2d(.) 2e(.), and R-3(.) were generated and isolated as stable solids. The molecular geometries determined by X-ray analysis indicated that these radicals adopt a zwitterionic structure, in which the unpaired electron is located on the quinodiimine unit but not on the pyridyl group. These novel radicals undergo facile and reversible 1e-oxidation as well as two-stage le-reduction. The observed amphotericity endows the radicals with electrical conductivities (10(-5) to 10(-9) S cm(-1)), and these thus represent a new motif for single-component organic semiconductors.

  DOI：

  10.1021/jo001352r

文献信息

• Pyrazino-tetracyanonaphthoquinodimethanes: sterically deformed electron acceptors affording zwitterionic radicals
  作者：Takanori Suzuki、Setsuko Miyanari、Hidetoshi Kawai、Kenshu Fujiwara、Takanori Fukushima、Tsutomu Miyashi、Yoshiro Yamashita

  DOI：10.1016/j.tet.2004.01.005

  日期：2004.2

  The X-ray analyses of the title electron acceptors (1) revealed their butterfly-shaped deformed geometry, which is not affected by the pyridyl group attached at 2-position of the pyrazino-TCNNQ skeleton. Small differences between the first and second reduction potentials (ca. 0.1 V) in pyrazino-TCNNQs show that their anion radicals (1(-.)) are prone to disproportionate into the neutral (1) and dianionic (1(2-)) species. The thermodynamically unstable anion radical species based on the pyrazino-TCNNQ skeleton could be isolated as inner salts upon electrochemical reduction of the derivatives having an N-methylpyridinium moiety at 2-position (2(+)). The zwitterionic open-shell species (2) constitute a novel class of radicals that exhibit semiconducting behavior as a single component thanks to the high electrochemical amphotericity. (C) 2004 Elsevier Ltd. All rights reserved.
• Single-Component Organic Semiconductors Based on Novel Radicals that Exhibit Electrochemical Amphotericity:  Preparation, Crystal Structures, and Solid-State Properties of <i>N,N</i><i>‘</i>-Dicyanopyrazinonaphthoquinodiiminides Substituted with an <i>N</i>-Alkylpyridinium Unit
  作者：Takanori Suzuki、Setsuko Miyanari、Yoshiaki Tsubata、Takanori Fukushima、Tsutomu Miyashi、Yoshiro Yamashita、Kenichi Imaeda、Takayuki Ishida、Takashi Nogami

  DOI：10.1021/jo001352r

  日期：2001.1.1

  N,N'-Dicyanonaphthoquinodiimines fused with a pyrazine ring 1 were prepared from the corresponding quinones 4. The new accepters 1 have a planar pi -system and undergo reversible two-stage 1e-reduction. Quaternization of the pyridyl substituent in 1d-f gave pyridinium derivatives 2d(+), 2e(+), and R-3(+), respectively, which are stronger accepters that undergo three-stage le-reduction. Upon electrochemical. reduction of these cations, novel radicals 2d(.) 2e(.), and R-3(.) were generated and isolated as stable solids. The molecular geometries determined by X-ray analysis indicated that these radicals adopt a zwitterionic structure, in which the unpaired electron is located on the quinodiimine unit but not on the pyridyl group. These novel radicals undergo facile and reversible 1e-oxidation as well as two-stage le-reduction. The observed amphotericity endows the radicals with electrical conductivities (10(-5) to 10(-9) S cm(-1)), and these thus represent a new motif for single-component organic semiconductors.