4H-1,1-Dioxo-2,6-dimethyl-4-(dicyanomethylidene)thiopyran | 97671-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 4H-1,1-Dioxo-2,6-dimethyl-4-(dicyanomethylidene)thiopyran
• 英文别名: 2-(2,6-dimethyl-1,1-dioxothiopyran-4-ylidene)propanedinitrile
• CAS: 97671-93-7
• 化学式: C₁₀H₈N₂O₂S
• 分子量: 220.252
• InChiKey: QYMVCBWCWBVJAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-Dimethyl-4H-thiopyran-4-one 1,1-dioxide 、 丙二腈 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以43%的产率得到4H-1,1-Dioxo-2,6-dimethyl-4-(dicyanomethylidene)thiopyran
  参考文献：
  名称：

  Electron Transport in 4H-1,1-Dioxo-4-(dicyanomethylidene)thiopyrans. Investigation of x-ray Structures of Neutral Molecules, Electrochemical Reduction to the Anion Radicals, and Absorption Properties and EPR Spectra of the Anion Radicals

  摘要：

  A series of 4H-1,1-dioxo-4-(dicyanomethylidene)thiopyrans 1-15, which are useful as electron-transport materials in xerography, were prepared by condensation of malononitrile with the corresponding 4H-1,1-dioxothiopyran-4-one. X-ray crystal structures of 1-5 were indicative that the thiopyran ring is planar in 1, 2, and 5 and is boat shaped in the tert-butyl-substituted derivatives 3 and 4. The 2-thienyl substituent in 5 is rigorously coplanar with the thiopyran ring in 5. The anion radicals of 1-6, which were prepared by electrochemical or lithium naphthalenide reduction, were examined by EPR and absorption spectroscopy. The experimental spin densities as determined at atomic centers by EPR spectroscopy are consistent with values determined by an ab initio calculation on the anion radical bf 9. The reduction potentials of 1-15 as measured by second-harmonic AC voltammetry: (SHACV) correlated with the sum of Hammett substituent constants at the 2- and 6-positions. Coulometric reduction and reoxidation was indicative of reversible one-electron processes in these systems. Parent compound 2 gave completely irreversible reduction even by SHACV. Electron mobilities of thin films of 3, 4, or 15 molecularly dispersed in a polyester binder were found to increase with increased planarity of the electron-transport material and increased pi-delocalization of the unpaired spin.

  DOI：

  10.1021/jo00111a028

文献信息

• ALUMINUM CHELATE COMPLEX FOR ORGANIC EL MATERIAL
  申请人：MATSUO Shinji

  公开号：US20100256377A1

  公开（公告）日：2010-10-07

  This invention provides an organic EL material useful for the emissive layer of an organic EL element which deteriorates little in luminance when operated over a prolonged period of time and shows excellent durability. The material is an aluminum chelate complex which is represented by general formula (1) in which Ar 1 is a mono- or bicylic arylene group, Ar 2 is a mono- or bicyclic aryl group, R 1 -R 6 are hydrogen or hydrocarbon groups containing 1-8 carbon atoms and contains a compound represented by general formula (1) in which Ar 2 is a halogen as an impurity in an amount of 350 wt ppm or less.

  这项发明提供了一种有机EL材料，适用于有机EL元件的发射层，在长时间运行时，其亮度几乎不会退化，并且具有出色的耐久性。该材料是一种铝螯合物复合物，其由一般式（1）表示，其中Ar1是单环或双环芳烃基团，Ar2是单环或双环芳基团，R1-R6是含有1-8个碳原子的氢或烃基团，并且含有一种以卤素为杂质的化合物，其以350重量ppm或更少的量表示。
• Aluminum chelate complex for organic el material
  申请人：Matsuo Shinji

  公开号：US20070054148A1

  公开（公告）日：2007-03-08

  This invention provides an organic EL material useful for the emissive layer of an organic EL element which deteriorates little in luminance when operated over a prolonged period of time and shows excellent durability. The material is an aluminum chelate complex which is represented by general formula (1) in which Ar 1 is a mono- or bicylic arylene group, Ar 2 is a mono- or bicyclic aryl group, R 1 —R 6 are hydrogen or hydrocarbon groups containing 1-8 carbon atoms and contains a compound represented by general formula (1) in which Ar 2 is a halogen as an impurity in an amount of 350 wt ppm or less.

  本发明提供了一种有机EL材料，可用于有机EL元件的发光层，该材料在长时间运行时发光度几乎不会降低，并表现出优异的耐久性。该材料是一种铝螯合物复合物，其由一般式（1）表示，其中Ar1是单环或双环芳基烃基，Ar2是单环或双环芳基基团，R1-R6是含有1-8个碳原子的氢或碳氢基团，并且含有一种以卤素为杂质的化合物，其量为350重量ppm或以下。
• Electron transporting compounds, electrophotographic layers and elements comprising such compounds
  申请人：EASTMAN KODAK COMPANY (a New Jersey corporation)

  公开号：EP0157492A2

  公开（公告）日：1985-10-09

  An electrophotographic layer comprising an electrically insulating binder and an electron donar additionally comprises, as an electron transporting compound, a 4H-thiopyran-1,1-dioxide having an electron-withdrawing group in the 4-position and a half-wave reduction potential more positive than -0.5 volt as measured against a saturated calomel electrode. Novel compounds useful as the electron transporting compound are provided.

  由电绝缘粘合剂和电子捐赠剂组成的电致发光层，作为电子传输化合物，还包括一种4H-噻喃-1,1-二氧化物，该化合物在4位上有一个电子吸收基团，对饱和甘汞电极测量的半波还原电位大于-0.5伏。提供了可用作电子传输化合物的新型化合物。
• NOVEL ELECTROCHROMIC MATERIALS AND DEVICES
  申请人：Eastman Kodak Company

  公开号：EP1740672B1

  公开（公告）日：2010-04-21
• US4514481A
  申请人：——

  公开号：US4514481A

  公开（公告）日：1985-04-30