2,3,5,6-tetramethyl-7,7,8,8-tetracyano-para-quinodimethane | 97218-71-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 醌二甲烷类
• 英文名称: 2,3,5,6-tetramethyl-7,7,8,8-tetracyano-para-quinodimethane
• 英文别名: 2,3,5,6-tetramethyl-7,7,8,8-tetracyano-p-quinodimethane；tetramethyltetracyano-p-quinodimethane；Tetramethyltetracyanoquinodimethane；TMTCNQ；Tetracyanochinodimethan；2,2'-(2,3,5,6-Tetramethylcyclohexa-2,5-diene-1,4-diylidene)dimalononitrile；2-[4-(dicyanomethylidene)-2,3,5,6-tetramethylcyclohexa-2,5-dien-1-ylidene]propanedinitrile
• CAS: 97218-71-8
• 化学式: C₁₆H₁₂N₄
• 分子量: 260.298
• InChiKey: BZRKHSIULPIDFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetramethyl-7,7,8,8-tetracyano-para-quinodimethane 、 2,3-二甲基苯并噻唑鎓碘化物 在 N-甲基哌啶 作用下， 以 乙腈 为溶剂， 反应 144.33h， 以8.4%的产率得到2-(4-{2-[(Z)-(3-methyl-1,3-benzothiazol-3-ium-2-yl)methylidene]-9-methyl-2,9-dihydropyrrolo[3,2-b][1,4]benzothiazin-3-yl}-2,3,5,6-tetramethylphenyl)malononitrile iodide
  参考文献：
  名称：

  电子受体畸变：涉及四甲基-TCNQ的意外反应

  摘要：

  涉及给体N-甲基-2-甲基苯并噻唑鎓的反应–和N-（1-丙基）-2-甲基苯并噻唑碘化物在合适的碱存在下，用受体2,3,5,6-四甲基-7,7,8,8-四氰基-p-喹二甲烷（TMTCNQ）分离出新的[（Z）-β-（N-烷基苯并噻唑-3-基-2-基）-α-氰基-2,3,5,6-四甲基-4-苯乙烯基]二氰基甲烷发色团。在延长的反应时间下，结合了变形的TMTCNQ的电荷转移化合物的这些第一个例子电子受体，在丙烯腈官能团上进行进一步反应，从而促进了新型化合物的合成 硫吗啉基的电荷转移化合物经由硫介导的环化反应。第二个反应说明了一种从根本上说是新型的基于TCNQ的化学反应，这一点已得到以下方面的证实：X射线晶体学 和 高分辨率质谱。可能的反应机理形成硫吗啉-基于 发色团 被认为。

  DOI：

  10.1039/b201862b
• 作为产物：
  描述：

  2,3,5,6-四甲基-1,4-苯二乙腈 在 N-氯代丁二酰亚胺 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 2,3,5,6-tetramethyl-7,7,8,8-tetracyano-para-quinodimethane
  参考文献：
  名称：

  立体拥挤的四氰基-喹啉甲烷：2,3,5,6-四甲基-7,7,8,8-四氰基-喹啉=甲烷的合成与结构

  摘要：

  已经合成了空间拥挤的2,3,5,6-四甲基-7,7,8,8-四氰基=-喹二甲烷（= 1）。基于X射线结构分析，讨论了（= 1）的独特空间结构。

  DOI：

  10.1016/s0040-4039(00)94784-1

文献信息

• Molecular diodes and ultra-thin organic rectifying junctions: Au–S–C_nH_2n–Q3CNQ and TCNQ derivatives
  作者：Geoffrey J. Ashwell、Katarzyna Moczko、Marta Sujka、Anna Chwialkowska、L. R. Hermann High、Daniel J. Sandman

  DOI：10.1039/b616607e

  日期：——

  Attempts to obtain derivatives of the molecular diode, 2-4-[1-cyano-2-(1-(ω-acetylsulfanylalkyl)-1H-quinolin-4-ylidene)-ethylidene]-cyclohexa-2,5-dienylidene}-malonitrile [1, CH3CO–S–CnH2n–Q3CNQ], from either 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-p-quinodimethane (TCNQF4) or 2,3,5,6-tetramethyl-7,7,8,8-tetracyano-p-quinodimethane (TMTCNQ) result in ring closure via the cyano group of the π-bridge and yield di-substituted analogues: 2-2,3,5,6-tetrafluoro-4-[6-(10-acetylsulfanyldecyl)-3-(1-(10-acetylsulfanyldecyl)-1H-quinolin-4-ylidenemethyl)-6H-benzo[f][1,7]naphthyridin-2-ylidene]-cyclohexa-2,5-dienylidene}-malonitrile (2a) and the 2,3,5,6-tetramethyl derivative (2b). Self-assembled monolayers (SAMs) of these donor–(π-bridge)–acceptor molecular diodes exhibit asymmetric current–voltage characteristics with electron flow at forward bias from the top contact to surface C(CN)2 groups. Comparison is made with I–V curves from ultra-thin films of an organic rectifying junction in which TCNQ− is electron-donating and a donor–(σ-bridge)–acceptor diode in which TCNQ° is electron-accepting.

  试图从 2,3,5,6-四氟-7,7,8,8-四氰基-对二醌甲烷（TCNQF4）或 2,3,5,6-四甲基-7,7,8,8-四氰基-对二醌甲烷（TCNQF4）中获得分子二极管 2-4-[1-氰基-2-(1-(Ï-乙酰硫烷基)-1H-喹啉-4-亚基)-亚乙基]-环己-2,5-二烯基}-丙二腈[1, CH3COâSâCnH2nâQ3CNQ] 的衍生物、2-2,3,5,6-四氟-7,7,8,8-四氰基对二醌甲烷 (TCNQF4) 或 2,3,5,6-四甲基-7,7,8,8-四氰基对二醌甲烷 (TMTCNQ)，通过 Ï-桥的氰基实现闭环，生成二取代类似物：2-2,3,5,6-tetrafluoro-4-[6-(10-acetylsulfanyldecyl)-3-(1-(10-acetylsulfanyldecyl)-1H-quinolin-4-ylidenemethyl)-6H-benzo[f][1,7]萘啶-2-亚基]-环己-2,5-二烯亚基}-丙二腈（2a）和 2,3,5,6-四甲基衍生物（2b）。这些供体â（Ï-桥）â受体分子二极管的自组装单层（SAM）显示出不对称的电流电压特性，在正向偏压下电子从顶部接触流向表面的 C(CN)2 基团。我们将其与以 TCNQâ 为电子供体的有机整流结和以 TCNQ° 为电子受体的供体â（Ï-桥）â-受体二极管的超薄薄膜的 IâV 曲线进行了比较。
• Tetramethyltetracyanoquinodimethane
  作者：Aravinda Kini、Michael Mays、Dwaine Cowan

  DOI：10.1039/c39850000286

  日期：——

  Synthesis of the title compound, description of its novel single wave, two-electron reduction, and preliminary data on the electrical switching of its copper salt are presented.

  介绍了标题化合物的合成，其单波描述，两电子还原的描述以及有关其铜盐电切换的初步数据。
• Dibenzoborole-based compound and organic light emitting device including the same
  申请人：SAMSUNG DISPLAY CO., LTD.

  公开号：US10236453B2

  公开（公告）日：2019-03-19

  A dibenzoborole-based compound and an organic light-emitting device including the same. The dibenzoborole-based compound is represented by the formula A1-(A2)n1, wherein A1 may be selected from specific aromatic and non-aromatic carbocycles and heterocycles, n1 may be an integer selected from 1 to 10, and each A2 moiety may independently be selected from a group represented by Formula 2: The dibenzoborole-based compound may be included in the hole transport region or hole transport layer. When the dibenzoborole-based compound has strong electron acceptor characteristics, the hole injection barrier between the anode and the organic layer may be reduced, and thus, an organic light-emitting device including the dibenzoborole-based compound may have high efficiency and a long lifespan.

  一种二苯并硼基化合物和包括该化合物的有机发光器件。二苯并硼基化合物由式 A1-(A2)n1 表示，其中 A1 可以选自特定的芳香族和非芳香族碳环和杂环，n1 可以是选自 1 到 10 的整数，每个 A2 分子可以独立地选自式 2 所代表的基团： 二苯并硼基化合物可包含在空穴传输区域或空穴传输层中。当二苯并硼基化合物具有较强的电子受体特性时，阳极和有机层之间的空穴注入势垒可以降低，因此，包含二苯并硼基化合物的有机发光器件可以具有较高的效率和较长的使用寿命。
• Borole compound and organic light-emitting device including the same
  申请人：Samsung Display Co., Ltd.

  公开号：US10259996B2

  公开（公告）日：2019-04-16

  A borole compound is represented by Formula 1: X11—(R11)b11. X11, R11, and b11 are as defined herein. An organic light-emitting device includes the borole compound. The organic light-emitting device includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer. The organic layer includes the borole compound.

  硼烯化合物由式 1 表示：X11-(R11)b11。X11、R11 和 b11 如本文所定义。有机发光器件包括硼烯化合物。有机发光器件包括第一电极、第二电极以及位于第一电极和第二电极之间的有机层，有机层包括发射层。有机层包括硼烯化合物。
• New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives
  作者：Martin R. Bryce、Stephen R. Davies、Andrew M. Grainger、Michael B. Hursthouse、Mohammed Mazid、Rainer Bachmann、Fabian Gerson、Jonas Hellberg

  DOI：10.1021/jo00032a017

  日期：1992.3

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.