[1,3]dithiolo[4,5-b]pyrazine-2-one | 4428-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: [1,3]dithiolo[4,5-b]pyrazine-2-one
• 英文别名: pyrazine-1,3-dithiole-2-one；pyrazino-1,3-dithiole-2-one；[1,3]Dithiolo[4,5-b]pyrazin-2-one
• CAS: 4428-04-0
• 化学式: C₅H₂N₂OS₂
• 分子量: 170.216
• InChiKey: DQCZRPBDNDDYFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1,3]dithiolo[4,5-b]pyrazine-2-one 在 亚磷酸三乙酯 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Papavassiliou, G.C.; Gionis, V.; Yiannopoulos, S.Y., Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 156, p. 277 - 288

  摘要：

  DOI：
• 作为产物：
  描述：

  pyrazine-2,3-trithiocarbonate 在 mercury(II) diacetate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以69%的产率得到[1,3]dithiolo[4,5-b]pyrazine-2-one
  参考文献：
  名称：

  Extended TTF-type donors fused with pyrazine units; synthesis and characterization

  摘要：

  Pyrazinedicyanoethylthiotetrathiafulvalene, (pzdc-TTF) (1a), an extended TIFF fused with a pyrazine moiety and also a dithiolene ligand precursor, was synthesized through a cross-coupling with triethyl phosphite between pyrazine-1,3-dithiole-2-thione (I) and 4,5-bis(2-cyanoethylthio)-1,3-dithiole-2-one (III). This reaction also yields to dipyrazine TIFF derivative (1b) and 2,3,6,7-Tetrakis(2-cyanoethylthio)TTF (1c), resulting from the self-coupling reactions of the thione (I) and ketone (III). The crystal structure of 1a is composed by pairs of head to head donor stacks of pzdc-TTF molecules along b in opposite orientations. Single crystals of 1b revealed a new polymorph with a face-to-face pi-stacking motif. The electrochemical properties of 1a studied by cyclic voltammetry (CV) in DMF, shows two single electron oxidation processes typical of TTF-based donors; one pair of asymmetric redox waves centered at 627 mV versus Ag/Ag+ is ascribed to the couple [pzdc-TTF](+)/[pzdc-TTF](2+), and one pair of quasi-reversible redox waves centered at 430 mV is ascribed to the couple [pzdc-TTF](0)/[pzdc-TTF](+). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.131

文献信息

• Synthesis of Pyrazinodithiadiselenafulvalenes. New Unsymmetrical π-Donors
  作者：George C. Papavassiliou、Stelios Y. Yiannopoulos、John S. Zambounis、Keiji Kobayashi、Kisaburo Umemoto

  DOI：10.1246/cl.1987.1279

  日期：1987.7.5

  Unsymmetrical dithiadiselenafulvalenes, which are annelated on the 1,3-dithiole or 1,3-dise1enole moiety to a 1,4-pyrazine ring, have been prepared by the cross coupling method and characterized as electron-donors for use in conductive charge-transfer salts.

  通过交叉偶联法制备了不对称的二硫代二硒富戊烯，它们在 1,3-二硫代或 1,3-二硒代上环化成一个 1,4-吡嗪环，并被表征为可用于导电电荷转移盐的电子供体。
• Papavassiliou, G. C.; Kakoussis, V. C.; Lagouvardos, D. J., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 181, p. 171 - 184
  作者：Papavassiliou, G. C.、Kakoussis, V. C.、Lagouvardos, D. J.、Mousdis, G. A.

  DOI：——

  日期：——
• PAPAVASSILIOU, G. C.;MOUSDIS, G. A.;YIANNOPOULOS, S. Y.;KAKOUSSIS, V. C.;+, SYNTH. MET., 27,(1988) N-4, C. B373-B378
  作者：PAPAVASSILIOU, G. C.、MOUSDIS, G. A.、YIANNOPOULOS, S. Y.、KAKOUSSIS, V. C.、+

  DOI：——

  日期：——
• PAPAVASSILIOU, GEORGE C.;YIANNOPOULOS, STELIOS Y.;ZAMBOUNIS, JOHN S.;KOBA+, CHEM. LETT.,(1987) N 7, 1279-1282
  作者：PAPAVASSILIOU, GEORGE C.、YIANNOPOULOS, STELIOS Y.、ZAMBOUNIS, JOHN S.、KOBA+

  DOI：——

  日期：——
• High Performance n- and p-Type Field-Effect Transistors Based on Tetrathiafulvalene Derivatives
  作者：Naraso、Jun-ichi Nishida、Daisuke Kumaki、Shizuo Tokito、Yoshiro Yamashita

  DOI：10.1021/ja0630083

  日期：2006.8.1

  The first n-type FET based on TTF derivatives was prepared. TTF derivatives with halogeno-substituted quinoxaline rings showed excellent n- or p-type performances with high carrier mobilities. Introduction of halogen groups determined the FET polarity by controlling the HOMO and LUMO levels of the molecules. The pi-stacking structures were observed in the single crystals of tetrahalogeno-TTFs.