trans-4-(N,N-diphenylamino)-4'-(methoxycarbonyl)stilbene | 666830-55-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trans-4-(N,N-diphenylamino)-4'-(methoxycarbonyl)stilbene
• 英文别名: methyl 4-[(E)-2-[4-(N-phenylanilino)phenyl]ethenyl]benzoate
• CAS: 666830-55-3
• 化学式: C₂₈H₂₃NO₂
• 分子量: 405.496
• InChiKey: VTCZXTYHODWNMY-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-4-(N,N-diphenylamino)-4'-(methoxycarbonyl)stilbene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到trans-4-(N,N-diphenylamino)-4'-(hydroxymethyl)stilbene
  参考文献：
  名称：

  Zn(II)-Induced Ground-State π-Deconjugation and Excited-State Electron Transfer in N,N-Bis(2-pyridyl)amino-Substituted Arenes

  摘要：

  The synthesis and X-ray crystal structures of two N,N-bis(2-pyridyl)amino (dpa)-substituted aromatic systems (Ar-dpa) 1 (Ar = 4,4'-disubstituted trans-stilbene) and 2 (Ar = 1,4-disubstituted benzene) and their ZnCl2 complexes (1/ZnCl2 and 2/ZnCl2) are reported. The fluoroionophoric behavior of 1-2 in response to Zn(II) in acetonitrile also has been investigated. In addition, compound 3DPA has been prepared and served as a pi-deconjugated model for 1DPA. The observed crystal structures for 1/ZnCl2 and 2/ZnCl2 Could be divided into two distinct types, the planar and the twisted forms, depending on the aryl-dpa (C-ph-NC3) dihedral angle. The twisted form is more favorable for these complexes unless the arene has a strong "push-pull" character. Nonetheless, the degree of pi-conjugation between the N-pyridyl and the N-aryl group is reduced in both complex forms when compared with the free ligands. Such a Zn(II)-induced pi-deconjugation not only directly affects the internal charge transfer (ICT) fluorescence of the dpa-substituted stilbenes but also facilitates the occurrence of photoinduced electron transfer (PET) from the stilbene donor to the dpa/Zn(II) acceptor. The PET process is particularly important in accounting for the observed Zn(II)-induced fluorescence quenching for 1DPA as well as 3DPA.

  DOI：

  10.1021/jo049902z
• 作为产物：
  描述：

  4-溴苄基亚磷酸二乙酯 在 1,1'-双(二苯基膦)二茂铁 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium hydride 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 trans-4-(N,N-diphenylamino)-4'-(methoxycarbonyl)stilbene
  参考文献：
  名称：

  Spectroscopic Correlations between Supermolecules and Molecules. Anatomy of the Ion-Modulated Electronic Properties of the Nitrogen Donor in Monoazacrown-Derived Intrinsic Fluoroionophores

  摘要：

  The synthesis, absorption and emission spectra, fluorescence quantum yields, and fluorescence lifetimes of three compound series of trans-4,4'-disubstituted aminostilbenes (1-3) are reported. The chromo-/fluoroionophoric behavior of the monoaza-15-crown-5- (A15C5) and monoaza-18-crown-6 (A18C6)-derived species (1A(5)-3A(5) and 1A(6)-3A(6)) in acetonitrile and dichloromethane are also investigated. Great similarities in electronic spectroscopic properties (chemical shifts, wavelength, intensity, and lifetime) between the metal ion-complexed supermolecules and the corresponding chloro-substituted molecules have been observed: namely, 1A(5)/Ca2+-3A(5)/Ca2+ similar to 1A(6)/Ba2+-3A(6)/ Ba(2+)similar to 1C-3C in acetonitrile and 1A(5)/Na+-2A(5)/Na+ similar to 1A(6)/K+-2A(6)/K+ similar to 1C-2C in dichloromethane. Such spectroscopic correlations allow us to define the metal ion-modulated electronic character of the azacrown nitrogen atom in the ground and excited states and, in turn, to gain insights into the observed fluoroionophoric behavior of these probes in terms of the size and direction of fluorescence shifts and intensity variations.

  DOI：

  10.1021/jo035462k