1,3,5-tris(2',2'-ethenyldicarbonnitrile)benzene | 186508-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3,5-tris(2',2'-ethenyldicarbonnitrile)benzene
• 英文别名: 1,3,5-tris(2,2-dicyanovinyl)benzene；2-[[3,5-Bis(2,2-dicyanoethenyl)phenyl]methylidene]propanedinitrile；2-[[3,5-bis(2,2-dicyanoethenyl)phenyl]methylidene]propanedinitrile
• CAS: 186508-05-4
• 化学式: C₁₈H₆N₆
• 分子量: 306.286
• InChiKey: JVXXEKBZOXWKMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  1,3,5-tris(2',2'-ethenyldicarbonnitrile)benzene 在 甲酸:三乙胺 1:1 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以96%的产率得到
  参考文献：
  名称：

  Symmetrical Tris(4,6-diamino-5-methylene-2-pyrimidones): New Building Blocks for Self-Assembly of Hollow Spherical Supramolecules Locked by Hydrogen Bonds

  摘要：

  描述了三(嘧啶酮)1a,b的简明合成。分子建模研究表明，所制备的模型1a,b都能够在形成由18个氢键锁定的球形二聚体的情况下自组装。在所有常见溶剂中的极端不溶性阻止了对溶液中自组装的研究。在固态和气相中提供了支持自组装的间接证据。

  DOI：

  10.1135/cccc19961464
• 作为产物：
  描述：

  1,3,5-三(溴甲基)苯 在 哌啶 、 2-硝基丙烷 、 sodium ethanolate 作用下， 以 乙醇 、 二甲基亚砜 、 正丁醇 为溶剂， 反应 11.0h， 生成 1,3,5-tris(2',2'-ethenyldicarbonnitrile)benzene
  参考文献：
  名称：

  Symmetrical Tris(4,6-diamino-5-methylene-2-pyrimidones): New Building Blocks for Self-Assembly of Hollow Spherical Supramolecules Locked by Hydrogen Bonds

  摘要：

  描述了三(嘧啶酮)1a,b的简明合成。分子建模研究表明，所制备的模型1a,b都能够在形成由18个氢键锁定的球形二聚体的情况下自组装。在所有常见溶剂中的极端不溶性阻止了对溶液中自组装的研究。在固态和气相中提供了支持自组装的间接证据。

  DOI：

  10.1135/cccc19961464

文献信息

• Self-Assembly and Catalytic Reactivity of BINOL-Bridged Bis(phenanthroline) Metallocages
  作者：Kai-Yu Cheng、Shi-Cheng Wang、Yu-Sheng Chen、Yi-Tsu Chan

  DOI：10.1021/acs.inorgchem.7b02540

  日期：2018.4.2

  Upon treatment with ZnII ions, a series of BINOL-bridged bis(phenanthroline) ligands was self-assembled into [M2L3] metallocages, which were carefully characterized by NMR spectroscopy and ESI-MS spectrometry. Among them, a racemic mixture of the BINOL-bridged bis(phenanthrolines) underwent chiral self-sorting to afford two homochiral metallocages. The narcissistic self-sorting process of the metallocages

  经Zn II离子处理后，将一系列BINOL桥联的双（菲咯啉）配体自组装为[M 2 L 3 ]金属位点，并通过NMR光谱学和ESI-MS光谱学对其进行了仔细表征。其中，由BINOL桥联的双（菲咯啉）的外消旋混合物进行手性自分选，得到两个同手性金属位点。在具有变化的连接位置的结构异构双（菲咯啉）的络合反应中观察到金属位点的自恋自选过程。此外，内羟基官能化金属位点[Zn 2 （S）-L2 OH } 3对芳族三甲醛与丙二腈的Knoevenagel缩合反应具有催化活性和底物选择性。
• Crystal Structure of Three Compounds Related to Triphenylene and Tetracyanoquinodimethane.
  作者：Thomas L. Andresen、Frederik C. Krebs、Mogens Larsen、Niels Thorup、Harri Lönnberg、Shi-Ping Yan、Geng-Lin Wang、Xin-Kan Yao、Hong-Gen Wang、J. -P. Tuchagues、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0410

  日期：——

  The crystal structures of a charge-transfer complex of triphenylene with 1,3,5-tris(2,2-dicyanovinyl) benzene (1), a complex of 2,3,6,7,10,11-hexamethoxytriphenylene with 2,5-dichlorotetracyanoquinodimethane (2) and also 2,5-dichlorotetracyanoquinodimethane itself (3) have been determined. Compound 1 is triclinic, space group P (1) over bar, with a = 7.055(1), b = 11.026(2), c = 17.214(3) Angstrom. alpha = 96.59 (3), beta = 90.34(3), gamma = 91.61(3)degrees. Compound 2 is triclinic, space group P (1) over bar, with a = 12.228(2), b = 12.994(3), c = 13.702(3) Angstrom, alpha = 70.72(3), beta = 83.73(3), gamma = 66.06(3)degrees. Compound 3 is monoclinic, space group I2/a (C2/c), with a = 13.692(3), b = 7.7183(15), c = 16.391(3) Angstrom, beta = 99.47(3)degrees. The structures of 1 and 2 consist of mixed stacks of donors and accepters. The structures of 2 and 3 both include 1,2-dichlorobenzene solvent molecules. Weak hydrogen bonds are present in the structures of 1 and 2. Based on comparisons of bond lengths the electronic charge-transfer in 2 has been estimated to be about 0.3 e. The synthesis of 1,3,5-tris(2,2-dicyanovinyl) benzene is also reported.
• Molecular Design, Syntheses, and Physical Properties of Nonpolymeric Amorphous Dyes for Electron Transport
  作者：Katsuyuki Naito、Masatoshi Sakurai、Syun Egusa

  DOI：10.1021/jp963233e

  日期：1997.3.1

  Relationships between electrical properties and molecular structures for various nonpolymeric amorphous dyes were investigated. Absorption maximum wavelengths (lambda(obs)) for amorphous films were found to be nearly equal to those for solution samples. When the parameters of the used PPP-CI MO method were modified so as to reproduce the lambda(obs) values, the calculated HOMO and LUMO energy levels corresponded with the reported ionization potential (I-p) and electron affinity (E(A)) values. Electric carrier transport properties between dye films and metal electrodes (Au or Al) were found to be correlated with the HOMO and LUMO levels. For strong donor and acceptor dyes, impurity carrier effects were generally observed. For weak donor and acceptor dyes, carrier injection was difficult. Carrier injection phenomena without the influence of impurities were observed for moderate donor and acceptor dye films. Amorphous dyes with cyanovinyl substituents or oxadiazole rings were designed to allow reversible electron transport and were newly synthesized.