hexa(4-cyanophenyl)trimethylenecyclopropane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: hexa(4-cyanophenyl)trimethylenecyclopropane
• 英文别名: hexakis(4-cyanophenyl)[3]radialene；4-[[2,3-Bis[bis(4-cyanophenyl)methylidene]cyclopropylidene]-(4-cyanophenyl)methyl]benzonitrile
• 化学式: C₄₈H₂₄N₆
• 分子量: 684.759
• InChiKey: RZFWWLNWDFXPQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  hexa(4-cyanophenyl)trimethylenecyclopropane 在 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Anion−π Interactions of Hexaaryl[3]radialenes

  摘要：

  Coordination polymers and discrete metallo-supramolecular assemblies of hexaaryl[3]radialene compounds exhibit intriguing structures with short anion to pi-centroid distances in the solid-state. Furthermore, these [3]radialene compounds display useful photophysical and electrochemical properties that make them ideal as potential platforms for anion receptors. In this study, hexafluoro[3]radialene was optimized to the MP2/aug-cc-pVTZ level of theory, and its complexes with halide anions were optimized to HF/6-31G+ +(d,p), MP2/6-31G++(d,p), M06-2X/6-31G++(d,p), and M06-2X/6-311G++(d,p) levels of theory. Hexafluoro[3]radialene was shown to have properties (large positive Q(zz) and areas of positive electrostatic surface potential) comparable to other compounds that show anion-pi interactions. The interaction energies of complexes of hexafluoro[3]radialene with halide anions were calculated and found to be favorable and equivalent to those of fluorinated aromatic compounds. A series of synthetically accessible hexaaryl[3]radialenes were optimized to HF/6-31G++(d,p) theory and their complexes with halides optimized to the M06-2X/6-31G++(d,p) level of theory. The calculated properties of the electron-deficient hexaaryl[3]radialenes also show large positive Q(zz) quadrupole moments and two areas of positive potential; at the [3]radialene core and the acidic aryl hydrogen atoms. The interaction energies of the complexes of hexaaryl[3]radialenes and halide anions were found to follow the trend F- > Cl- approximate to Br- and correlate with the electron-deficient nature of the [3]radialene. Close contacts were observed between the anion and the radialene core and the aryl hydrogen atoms, suggesting a combination of anion-pi and hydrogen bonding is important. Mass spectrometry was used to experimentally observe the complexes of a number of hexaaryl[3]radialenes with F-, Cl-, and Br- predicted computationally. Anion-[3]radialene complexes were successfully detected, and the stability of the complexes in tandem MS/MS experiments was found to support the computational results.

  DOI：

  10.1021/jp301464s
• 作为产物：
  描述：

  四氯环丙烯 、 4,4’-二氰基二苯甲烷 在 正丁基锂 、 氧气 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.5h， 以73%的产率得到hexa(4-cyanophenyl)trimethylenecyclopropane
  参考文献：
  名称：

  六芳基[3]二烯的合成、结构和性质

  摘要：

  通过四氯环丙烯与二芳基甲基阴离子反应，然后用氧氧化，合成了许多六苯基 [3] radialene 衍生物，收率中等至良好。发现二芳基甲烷的酸度高于二苯基甲烷的酸度是成功合成的重要因素。由此获得的六(4-碘苯基)[3]radialene的锂化和质子化导致了六苯基[3]radialene的第一次合成。这些六芳基[3]二烯是稳定的橙色至红色结晶物质。六（4-氰基苯基）[3]radialene 的 X 射线晶体学分析揭示了双三叶螺旋桨构象。苯基中的取代基对其性质的影响最明显地体现在它们的电化学还原电位上；在此处获得的六苯基[3]radialenes中，

  DOI：

  10.1246/bcsj.73.2109

文献信息

• Hexaaryl[3]radialenes
  作者：Tetsuya Enomoto、Takeshi Kawase、Hiroyuki Kurata、Masaji Oda

  DOI：10.1016/s0040-4039(97)00431-0

  日期：1997.4

  conjugate acids are more acidic than diphenylmethane with tetrachlorocyclopropene are found to afford hexaaryl-[3]radialenes in modest to good yields, thus leading to the first synthesis of hexaphenyl[3]radialene itself too; X-ray crystalographic analysis of hexakis(p-cyanophenyl)[3]radialene reveals a double three-bladed conformation.

  发现其共轭酸比二苯基甲烷更酸性的二芳基甲基阴离子与四氯环丙烯的反应可适度地获得良好的收率，从而得到六芳基[3] radi芳烃本身。六（对-氰基苯基）[3]芳烃的X射线晶体分析显示双三刃构象。
• Ruthenium complexes of hexakis(cyanophenyl)[3]radialenes and their di(cyanophenyl)methane precursors: synthesis, photophysical, and electrochemical properties
  作者：C.A. Hollis、X. He、C.J. Sumby

  DOI：10.1080/00958972.2014.915965

  日期：2014.4.18

  two isomeric cross-conjugated [3]radialenes [RuCp(PPh3)2(L)]PF6 and [RuCp*(dppe)}(L)]PF6 (L = hexakis(4-cyanophenyl)[3]radialene, 2; hexakis(3-cyanophenyl)[3]radialene, 3), and dinuclear complexes [RuCp(PPh3)2}2(L)](PF6)2 and [RuCp*(dppe)}2(L)](PF6)2 of the diarylmethane precursors (L = 4,4′-dicyanodiphenylmethane, 4; 3,3′-dicyanodiphenylmethane, 5) to the [3]radialenes. Considerable synthetic challenges

  交叉共轭配体的配位化学以及交叉共轭对金属-金属和金属-配体相互作用性质的影响受到的关注有限。为了探索交叉共轭的影响，合成了八种钌配合物，两种异构体交叉共轭的 [3]radialenes [RuCp(PPh3)2(L)]PF6 和 [RuCp*(dppe)}(L)] 的单核配合物PF6 (L = hexakis(4-cyanophenyl)[3]radialene, 2; hexakis(3-cyanophenyl)[3]radialene, 3) 和双核配合物 [RuCp(PPh3)2}2(L)](PF6) 2 和 [RuCp*(dppe)}2(L)](PF6)2 将二芳基甲烷前体（L = 4,4'-二氰基二苯基甲烷，4；3,3'-二氰基二苯基甲烷，5）转化为 [3] 芴烯. 相当多的合成挑战只允许清洁分离多齿辐射烯 2 和 3 的单核配合物。 正如预期的那样，配位带正电的金属会导致配体
• ORGANIC LIGHT EMITTING DIODE AND ORGANIC LIGHT EMITTING DEVICE INCLUDING THE SAME
  申请人：LG DISPLAY CO., LTD.

  公开号：US20220209131A1

  公开（公告）日：2022-06-30

  An organic light emitting diode and an organic light emitting device including the same are discussed. The organic light emitting diode can include a first electrode, a second electrode facing the first electrode, and a first emitting part including a green emitting material layer and positioned between the first and second electrodes. The green emitting material layer can include a first host, a second host and a dopant, wherein at least one of the first host and the second host is deuterated.

  本文讨论了有机发光二极管和包括其的有机发光装置。有机发光二极管可以包括第一电极、朝向第一电极的第二电极，以及位于第一电极和第二电极之间的第一发射部分，该部分包括绿色发射材料层。绿色发射材料层可以包括第一主机、第二主机和掺杂剂，其中第一主机和/或第二主机至少有一个是氘代的。
• DIE VERWENDUNG VON OXOKOHLENSTOFF-, PSEUDOOXOKOHLENSTOFF- UND RADIALENVERBINDUNGEN
  申请人：Novaled GmbH

  公开号：EP3457451A1

  公开（公告）日：2019-03-20

  Die vorliegende Erfindung betrifft die Verwendung von Oxokohlenstoff-, Pseudooxokohlenstoff- und Radialenverbindungen als Ladungsinjektionsschicht, sowie deren Verwendung in elektronischen Bauelementen.

  本发明涉及氧化碳、假氧化碳和径向化合物作为电荷注入层的用途及其在电子元件中的使用。
• Oxocarbon-, pseudooxocarbon- and radialene compounds and their use
  申请人：Novaled GmbH

  公开号：US11342504B2

  公开（公告）日：2022-05-24

  The present invention relates to oxocarbon-, pseudooxocarbon- and radialene compounds as well as to their use as doping agent for doping an organic semiconductive matrix material, as blocker material, as charge injection layer, as electrode material as well as organic semiconductor, as well as electronic components and organic semiconductive materials using them.

  本发明涉及氧碳化合物、假氧碳化合物和辐射烯化合物，以及它们作为掺杂剂在 有机半导体基质材料、阻断材料、电荷注入层、电极材料和有机半导体中的用途，还 涉及使用它们的电子元件和有机半导体材料。