(E)-4-(((4-(benzo[d]oxazol-2-yl)phenyl)imino)methyl)-N,N-diethylaniline | 1346233-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-4-(((4-(benzo[d]oxazol-2-yl)phenyl)imino)methyl)-N,N-diethylaniline
• CAS: 1346233-01-9
• 化学式: C₂₄H₂₃N₃O
• 分子量: 369.466
• InChiKey: JCKDWLZVZXRAFB-KOEQRZSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.63
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氨基苯酚 在 polyphosphoric acid 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (E)-4-(((4-(benzo[d]oxazol-2-yl)phenyl)imino)methyl)-N,N-diethylaniline
  参考文献：
  名称：

  Novel highly emissive H-aggregates with aggregate fluorescence change in a phenylbenzoxazole-based system

  摘要：

  一种基于苯并噁唑的衍生物展现出新颖且高发射的H型聚集体。

  DOI：

  10.1039/c4cc02564d

文献信息

• Synthesis, Characterization, and Spectroscopic Investigation of Benzoxazole Conjugated Schiff Bases
  作者：Fabiano S. Santos、Tania M. H. Costa、Valter Stefani、Paulo F. B. Gonçalves、Rodrigo R. Descalzo、Edilson V. Benvenutti、Fabiano S. Rodembusch

  DOI：10.1021/jp206905f

  日期：2011.11.24

  Two Schiff bases were synthesized by reaction of 2-(4'-amino-phenyl)benzoxazole derivatives with 4-N,N-diethylaminobenzaldehyde. UV-visible (UV-vis) and steady-state fluorescence in solution were applied in order to characterize its photophysical behavior. The Schiff bases present absorption in the UV region with fluorescence emission in the blue-green region, with a large Stokes' shift. The UV-vis data indicates that each dye behaves as two different chromophores in solution in the ground state. The fluorescence emission spectra of the dye Sa show that an intramolecular proton transfer (ESIPT) mechanism takes place in the excited state, whereas a twisted internal charge transfer (TICT) state is observed for the dye 5b. Theoretical calculations were performed in order to study the conformation and polarity of the molecules at their ground and excited electronic states. Using density functional theory (DFT) methods at theoretical levels BLYP/Aug-SV(P) for geometry optimizations and B3LYP/6-311++G(2d,p) for single-point energy evaluations, the calculations indicate that the lowest energy conformations are in all cases nonplanar and that the dipole moments of the excited state relaxed structures are much larger than those of the ground state structures, which corroborates the experimental UV-vis absorption results.