2-(2-pyridyl)-5H,8H-5,8-bis(dicyanomethylene)quinoxaline | 144792-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(2-pyridyl)-5H,8H-5,8-bis(dicyanomethylene)quinoxaline
• 英文别名: 2-[8-(Dicyanomethylidene)-2-pyridin-2-ylquinoxalin-5-ylidene]propanedinitrile
• CAS: 144792-78-9
• 化学式: C₁₉H₇N₇
• 分子量: 333.311
• InChiKey: NCYVKTQKBHEYKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-pyridyl)-5H,8H-5,8-bis(dicyanomethylene)quinoxaline 、 三氟甲烷磺酸甲酯 以 1,2-二氯乙烷 为溶剂， 反应 27.0h， 以50%的产率得到2-(2-(5H,8H-5,8-bis(dicyanomethylene)quinoxalyl))-1-methylpyridinium triflate
  参考文献：
  名称：

  Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton

  摘要：

  Pyrazino-TCNQ (1a) prepared from 5,8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo-1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of la. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-pi-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 X 10(-5) S cm-1.

  DOI：

  10.1021/jo00051a015
• 作为产物：
  描述：

  3,6-二溴-1,2-苯二胺 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 copper(l) iodide 、 selenium(IV) oxide 、 sodium hydride 、 lead dioxide 、 potassium iodide 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 54.5h， 生成 2-(2-pyridyl)-5H,8H-5,8-bis(dicyanomethylene)quinoxaline
  参考文献：
  名称：

  Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton

  摘要：

  Pyrazino-TCNQ (1a) prepared from 5,8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo-1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of la. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-pi-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 X 10(-5) S cm-1.

  DOI：

  10.1021/jo00051a015

文献信息

• Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton
  作者：Yoshiaki Tsubata、Takanori Suzuki、Tsutomu Miyashi、Yoshiro Yamashita

  DOI：10.1021/jo00051a015

  日期：1992.12

  Pyrazino-TCNQ (1a) prepared from 5,8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo-1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of la. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-pi-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 X 10(-5) S cm-1.