(2Z,2'Z)-3,3'-(1,4-phenylene)bis(2-phenylacrylonitrile) | 58393-80-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2Z,2'Z)-3,3'-(1,4-phenylene)bis(2-phenylacrylonitrile)
• 英文别名: (cis,cis)-1,4-bis(2-cyano-2-phenylethenyl)benzene；1,4-bis(2-cyano-2-phenylethenyl)benzene；2,2'-diphenyl-3,3'-p-phenylene-di-acrylonitrile；2,2'-Diphenyl-3,3'-p-phenylen-di-acrylonitril；1.4-Bis-(β-cyan-styryl)-benzol；(Z)-3-[4-[(Z)-2-cyano-2-phenylethenyl]phenyl]-2-phenylprop-2-enenitrile
• CAS: 58393-80-9
• 化学式: C₂₄H₁₆N₂
• 分子量: 332.404
• InChiKey: WSDKHZCNLDFRFB-DFEHQXHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z,2'Z)-3,3'-(1,4-phenylene)bis(2-phenylacrylonitrile) 在 碘 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以83%的产率得到5,10-dicyano[5]helicene
  参考文献：
  名称：

  Facile Photochemical Synthesis of 5,10-Disubstituted [5]Helicenes by Removing Molecular Orbital Degeneracy

  摘要：

  Photocyclodehydrogenation is a key reaction to synthesize helicenes; however, because of overannulation, it is not applicable to the synthesis of [S]helicene. Introduction of a cyano group was found to remove the orbital degeneracy of the low-lying unoccupied MOs; consequently, the lowest excitation comprises a single transition involving the C-2-antisymmetric MO. Therefore, the problematic overannulation can be effectively suppressed. Moreover, in combination with the Knoevenagel reaction, a one-pot synthesis of 5,10-dicyano[5]helicene with 67% yield was accomplished.

  DOI：

  10.1021/ol5008718
• 作为产物：
  描述：

  对苯二甲醛 、 苯乙腈 在 potassium tert-butylate 、 四丁基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 、 叔丁醇 为溶剂， 反应 0.33h， 以70%的产率得到(2Z,2'Z)-3,3'-(1,4-phenylene)bis(2-phenylacrylonitrile)
  参考文献：
  名称：

  Supramolecular interaction-induced self-assembly of organic molecules into ultra-long tubular crystals with wave guiding and amplified spontaneous emission

  摘要：

  通过物理气相法成功制备了有机小分子1,4-双(2-氰基-2-苯基乙烯基)苯(BCPEB)的超长管状晶体（长度可达10毫米，直径为70微米）运输（PVT）方法。在晶体结构分析和密度泛函理论计算的基础上，我们表明这种管状晶体的形成是由BCPEB分子之间的支化氢键引起的。高结晶质量、高度有序的分子取向和中空拓扑结构使晶体表现出低光损耗（3 dB mm−1）和高偏振发射（偏振比约为20）的光波导发射行为。还研究了管状晶体的放大自发发射（ASE）特性；峰值波长和阈值处的净增益系数分别为 91.7 cm−1 和 36 kW cm−2。

  DOI：

  10.1039/c1jm14815j

文献信息

• Exploring the minimal structure of a wholly aromatic organogelator: simply adding two β-cyano groups to distyrylbenzene
  作者：Seong-Jun Yoon、Jong H. Kim、Jong Won Chung、Soo Young Park

  DOI：10.1039/c1jm14558d

  日期：——

  The minimal structure of a wholly π-conjugated aromatic organogelator was explored in this work to show that distyrylbenzene with simple β-cyano substitution (β-DCS) is highly efficient for gelation which is attributed to the cooperative interplay of π–π stacking and secondary bonding interactions of dipolar cyano groups.

  这项研究探索了完全Ï-共轭芳香族有机凝胶剂的最小结构，结果表明具有简单β-氰基取代（β-DCS）的二丙烯苯具有很高的凝胶效率，这归功于双极性氰基的ÏâÏ堆叠和次级键相互作用的协同作用。
• Kauffmann, Chemische Berichte, 1917, vol. 50, p. 526
  作者：Kauffmann

  DOI：——

  日期：——
• Facile Photochemical Synthesis of 5,10-Disubstituted [5]Helicenes by Removing Molecular Orbital Degeneracy
  作者：Natsuki Ito、Takashi Hirose、Kenji Matsuda

  DOI：10.1021/ol5008718

  日期：2014.5.2

  Photocyclodehydrogenation is a key reaction to synthesize helicenes; however, because of overannulation, it is not applicable to the synthesis of [S]helicene. Introduction of a cyano group was found to remove the orbital degeneracy of the low-lying unoccupied MOs; consequently, the lowest excitation comprises a single transition involving the C-2-antisymmetric MO. Therefore, the problematic overannulation can be effectively suppressed. Moreover, in combination with the Knoevenagel reaction, a one-pot synthesis of 5,10-dicyano[5]helicene with 67% yield was accomplished.
• Supramolecular interaction-induced self-assembly of organic molecules into ultra-long tubular crystals with wave guiding and amplified spontaneous emission
  作者：Yuanxiang Xu、Houyu Zhang、Feng Li、Fangzhong Shen、Huan Wang、Xianjie Li、Yang Yu、Yuguang Ma

  DOI：10.1039/c1jm14815j

  日期：——

  Ultra-long tubular crystals (length up to 10 mm and diameter of 70 μm) of a small organic functional molecule, 1,4-bis(2-cyano-2-phenylethenyl)benzene (BCPEB), are successfully prepared through a physical vapor transport (PVT) method. On the basis of crystal structural analysis and density functional theory calculations, we show that the formation of such tubular crystals is drawn by the branched hydrogen bonds between the BCPEB molecules. High crystalline quality, highly ordered molecular orientation, and hollow-like topological structure enable the crystal to exhibit optical wave guided emission behaviors with low optical loss (3 dB mm−1) and highly polarized emission (the polarized ratio is about 20). Amplified spontaneous emission (ASE) characteristics of the tubular crystals were also studied; the net gain coefficients at the peak wavelength and the threshold are 91.7 cm−1 and 36 kW cm−2, respectively.

  通过物理气相法成功制备了有机小分子1,4-双(2-氰基-2-苯基乙烯基)苯(BCPEB)的超长管状晶体（长度可达10毫米，直径为70微米）运输（PVT）方法。在晶体结构分析和密度泛函理论计算的基础上，我们表明这种管状晶体的形成是由BCPEB分子之间的支化氢键引起的。高结晶质量、高度有序的分子取向和中空拓扑结构使晶体表现出低光损耗（3 dB mm−1）和高偏振发射（偏振比约为20）的光波导发射行为。还研究了管状晶体的放大自发发射（ASE）特性；峰值波长和阈值处的净增益系数分别为 91.7 cm−1 和 36 kW cm−2。

表征谱图