6,7-dimethyl-2,3-quinoxalinedithiol | 80224-79-9

• 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: 6,7-dimethyl-2,3-quinoxalinedithiol
• 英文别名: 6,7-dimethyl-quinoxaline-2,3-dithiol；6,7-Dimethyl-1,4-dihydroquinoxaline-2,3-dithione
• CAS: 80224-79-9
• 化学式: C₁₀H₁₀N₂S₂
• 分子量: 222.335
• InChiKey: VCGHALHIQGMRLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,2-联吡啶)二氯铂(II) 、 6,7-dimethyl-2,3-quinoxalinedithiol 在 NaOH 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [Pt(6,7-dimethyl-quinoxaline-2,3-dithiolate)(1,10-phenanthroline)]
  参考文献：
  名称：

  Cummings, Scott D.; Eisenberg, Richard, Inorganic Chemistry, 1995, vol. 34, # 8, p. 2007 - 2014

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氯-6,7-二甲基喹喔啉 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 6,7-dimethyl-2,3-quinoxalinedithiol
  参考文献：
  名称：

  Synthesis of novel oxidizable polymerization sensitizers based on the dithiinoquinoxaline skeleton

  摘要：

  Novel dyes, based on the dithiinoquinoxaline skeleton, were synthesized and characterized using H-1 NMR spectroscopy and chemical ionization mass spectroscopy. Their spectral properties, such as absorption, emission spectra and quantum yield of fluorescence, were also measured. Electron donating properties of the title compounds were estimated on the basis of DFT calculations. The studied dyes were used as oxidizable sensitizers for 2,4,6-tris(trichloromethyl)-1,3,5-triazine (Tz). The dye/Tz photoredox pairs were found to be effective visible-wavelength initiators of free radical polymerization. The ability of these systems to act as photoinitiators strongly depended upon the free energy change of the photoinduced electron transfer from the excited dyes to Tz. It has been shown that the intermolecular electron transfer is the limiting step in the photopolymerization initiated by these studied initiator systems. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.09.006

文献信息

• Tuning the Excited-State Properties of Platinum(II) Diimine Dithiolate Complexes
  作者：Scott D. Cummings、Richard Eisenberg

  DOI：10.1021/ja951345y

  日期：1996.1.1

  Two series of Pt(diimine)(dithiolate) complexes have been prepared in order to investigate the effects of molecular design on the excited-state properties of this chromophore. The first series comprises Pt(dbbpy)(dithiolate) complexes where dbbpy = 4,4'-di-terr-butyl-2,2'-bipyridine and the dithiolates are 1-(tert-butylcarboxy)-1-cyanoethylene-2,2-dithiolate (tbcda), 1-diethylphosphonate-1-cyanoerhylene-2,2-dithiolate (cpdt), 6,7-dimethylquinoxaline-2,3-dithiolate (dmqdt), maleonitriledithiolate (mnt), and toluene-3,4-dithiolate (tdt). The second series comprises Pt(diimine)(tdt) complexes where the diimines are 3,4,7,8-tetramethyl-1,10-phenanthroline (tmphen), 4,4'-di-tert-butyl-2,2'-bipyridine (dbbpy), 4,4'-dimethyl-2,2'-bipyridine (dmbpy), 2,2'-bipyridine (bpy), 1,10-phenanthroline (phen), 5-chloro-1,10-phenanthroline (Cl-phen), 4,4'-dichloro-2,2'-bipyridine (Cl(2)bpy), and 4,4'-bis(ethoxycarbonyl)2,2'-bipyridine (EC-bpy). All of the compounds display solvatochromic absorption bands and solution luminescence, which are attributed to a common charge-transfer-to-diimine excited state. The excited-state energies can be tuned by approximately 1 eV through ligand variation. Solution lifetimes range from 1 ns to over 1000 ns and Phi(em) range from 6.4 x 10(-3) to less than 10(-5) in CH2Cl2. Based on these data, the nonradiative and radiative decay rate constants have been calculated. For the Pt(diimine)(tdt) series, the nonradiative decay rate constants increase exponentially with decreasing energy, in agreement with the Energy Gap Law, while those for the Pt(dbbpy)(dithiolate) complexes do not exhibit a similar correlation. Excited-state redox potentials have been estimated for all of the complexes from spectroscopic and electrochemical data. The ability to tune the driving force for bimolecular excited-state electron-transfer reactions has been demonstrated for eight of the complexes using reductive and oxidative quenching experiments.
• PAPAVASSILIOU, G. C.;YIANNOPOULOS, S. Y.;ZAMBOUNIS, J. S., CHEM. SCR., 27,(1987) N 2, 265-268
  作者：PAPAVASSILIOU, G. C.、YIANNOPOULOS, S. Y.、ZAMBOUNIS, J. S.

  DOI：——

  日期：——
• Cummings, Scott D.; Eisenberg, Richard, Inorganic Chemistry, 1995, vol. 34, # 8, p. 2007 - 2014
  作者：Cummings, Scott D.、Eisenberg, Richard

  DOI：——

  日期：——
• Synthesis of novel oxidizable polymerization sensitizers based on the dithiinoquinoxaline skeleton
  作者：Radosław Podsiadły、Jolanta Sokołowska

  DOI：10.1016/j.dyepig.2011.09.006

  日期：2012.3

  Novel dyes, based on the dithiinoquinoxaline skeleton, were synthesized and characterized using H-1 NMR spectroscopy and chemical ionization mass spectroscopy. Their spectral properties, such as absorption, emission spectra and quantum yield of fluorescence, were also measured. Electron donating properties of the title compounds were estimated on the basis of DFT calculations. The studied dyes were used as oxidizable sensitizers for 2,4,6-tris(trichloromethyl)-1,3,5-triazine (Tz). The dye/Tz photoredox pairs were found to be effective visible-wavelength initiators of free radical polymerization. The ability of these systems to act as photoinitiators strongly depended upon the free energy change of the photoinduced electron transfer from the excited dyes to Tz. It has been shown that the intermolecular electron transfer is the limiting step in the photopolymerization initiated by these studied initiator systems. (C) 2011 Elsevier Ltd. All rights reserved.