2,5-dibromo-N,N'-dicyano-1,4-benzoquinonediimine | 98507-12-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-dibromo-N,N'-dicyano-1,4-benzoquinonediimine
• 英文别名: 2,5-dibromo-N,N'-dicyanoquinonediimine；N,N'-dicyano-2,5-dibromo-p-benzoquinone bisimine；2,5-Dibromo-2,5-cyclohexadiene-1,4-diylidenebiscyanamide；(2,5-dibromo-4-cyanoiminocyclohexa-2,5-dien-1-ylidene)cyanamide
• CAS: 98507-12-1
• 化学式: C₈H₂Br₂N₄
• 分子量: 313.939
• InChiKey: FNYKSKUCLJKHGC-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：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dibromo-N,N'-dicyano-1,4-benzoquinonediimine 、 tetrakis(acetonitrile)copper(I) tetrafluoroborate 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Nonlinear Conductivity in Dicyanoquinonediimine Complexes

  摘要：

  Nonlinear conductivity is observed below the metal-insulator (M-I) transitions of molecular conductors, halogen-substituted (R-1,R-2-DCNQI)(2)Cu (DCNQI: dicyanoquinonediimine, R-1,R-2: methyl or halogen). Despite the difference of the M-I transition temperatures depending on the halogens, these compounds show nonlinear properties at similar low temperatures (<80 K), and the characteristics are regarded as "activation'' type. The complex of deuterated dimethyl-DCNQI (d(2)-DMeDCNQI)(2)Cu, which shows reentrant M-I-M transitions, exhibits irreversible switching from a low-conducting state to a high-conducting state in the intermediate I state. Since the Peierls distortion is irreversibly erased by the electric field, this phenomenon is called "Peierls memory''. In addition, "inverse'' nonlinear conductivity from a high-conducting state to a low-conducting state is observed at the low-temperature M state, which is not only entirely reversible but also accompanied by a new kind of rapid current oscillation in the order of 3 kHz. These observations demonstrate metastable nature of the intermediate I state.

  DOI：

  10.1143/jpsj.79.094703
• 作为产物：
  描述：

  2,5-二溴-1,4-苯醌 、 N-Trimethylsilyl-carbodiimid 在 四氯化钛 作用下， 以 二氯甲烷 、 Petroleum ether 为溶剂， 生成 2,5-dibromo-N,N'-dicyano-1,4-benzoquinonediimine
  参考文献：
  名称：

  Charge transfer complexes of tetrathio/seleno-fulvalene derivatives and

  摘要：

  一种新型的由N,N'-二氰基醌亚胺和富瓦烯衍生物组成的电荷转移复合物，其化学式为##STR1##和##STR2##，其中，在式I中，R.sup.1、R.sup.2、R.sup.3和R.sup.4彼此独立地为--H、--CH.sub.3、--C.sub.2 H.sub.5、--OCH.sub.3、--OC.sub.2 H.sub.5、--Cl和/或--Br，且R.sup.1和R.sup.2中的一个和/或R.sup.3和R.sup.4中的一个还可以是苯基或叔丁基，或者R.sup.1和R.sup.2和/或R.sup.3和R.sup.4共同形成##STR3##，且连接的芳香环未取代或取代，在式(II)中，R.sup.5、R.sup.6、R.sup.7和R.sup.8彼此独立地各自为--H、--CH.sub.3、--C.sub.2 H.sub.5、苯基、甲基苯基或甲氧基苯基，或者R.sup.5和R.sup.6和/或R.sup.7和R.sup.8共同形成##STR4##，其中n=3、4或5，##STR5##且X和Y彼此独立地为S或Se。在结晶状态下，电荷转移复合物具有电导性，因此可作为电半导体或光导体使用。新型的二氰基醌亚胺，其化学式为(I)，其中R.sup.1、R.sup.2、R.sup.3和R.sup.4具有上述含义，以及用于制备化合物(I)的新方法。

  公开号：

  US04578220A1

文献信息

• Crystal and electronic structures of conductive anion-radical salts, (2,5-R1R2-DCNQI)2Cu (DCNQI = N,N'-dicyanoquinonediimine; R1, R2 = CH3, CH3O, Cl, Br)
  作者：Reizo Kato、Hayao Kobayashi、Akiko Kobayashi

  DOI：10.1021/ja00196a032

  日期：1989.7

  Crystal structures of a series of highly conductive anion-radical salts with formula (2,5-Rsub 1},Rsub 2}-DCNQI)sub 2}Cu (DCNQI = N,Nprime}-dicyanoquinonediimine; Rsub 1}, Rsub 2} = CHsub 3}, CHsub 3}O, Cl, Br) have been studied at room temperature and 100 K. at room temperature, all these compounds are isostructural (tetragonal, space group I4sub 1}/a). The structure consists of a face-to-face

  一系列具有式 (2,5-Rsub 1},Rsub 2}-DCNQI)sub 2}Cu (DCNQI = N,Nprime}-二氰基醌二亚胺; Rsub 1}, Rsub 2} = CHsub 3}, CHsub 3}O, Cl, Br) 已在室温和 100 K 下进行研究。 ，空间群 I4sub 1}/a)。该结构由沿晶体 c 轴的面对面 DCNQI 柱组成。Cu 阳离子以 Dsub 2d} 扭曲四面体方式与 DCNQI 分子的 N 原子配位。该系统中的金属-绝缘体转变伴随着 c 轴的突然集中。X 射线卫星反射表明周期为 3c 的周期性晶格畸变出现在金属-绝缘体转变温度 (Tsub M-1}) 以下。
• Huenig, Siegfried; Kemmer, Martina; Meixner, Hubert, European Journal of Inorganic Chemistry, 1999, # 5, p. 899 - 916
  作者：Huenig, Siegfried、Kemmer, Martina、Meixner, Hubert、Sinzger, Klaus、Wenner, Hermann、et al.

  DOI：——

  日期：——
• Photochemical modification of magnetic properties in organic low-dimensional conductors
  作者：Toshio Naito、Akihiro Kakizaki、Makoto Wakeshima、Yukio Hinatsu、Tamotsu Inabe

  DOI：10.1016/j.jssc.2009.07.032

  日期：2009.10

  Magnetic properties of organic charge transfer salts Ag(DX)(2) (DX = 2,5-dihalogeno-N,N'-dicyanoquino-nediimine; X = Cl, Br, 1) were modified by UV irradiation from paramagnetism to diamagnetism in an irreversible way. The temperature dependence of susceptibility revealed that such change in magnetic behavior could be Continuously controlled by the duration of irradiation. The observation with scanning electron microprobe revealed that the original appearance of samples, e.g. black well-defined needle-shaped shiny single crystals, remained after irradiation irrespective of the irradiation conditions and the duration. Thermochemical analysis and X-ray diffraction Study demonstrated that the change in the physical properties were due to (partial) decomposition of Ag(DX)(2) to AgX, which was incorporated in the original Ag(DX)(2) lattices. Because the physical properties of low-dimensional organic conductors are very sensitive to lattice defects, even a small amount of AgX could effectively modify the electronic properties of Ag(DX)(2) Without making the original crystalline appearance collapse. (C) 2009 Elsevier Inc. All rights reserved.