The Synthesis And Photoelectric Properties Of The Novel Cyano-stilbene Derivatives

The organic photoelectric materials with aggregation induced emission activity have potential applications in the field of organic light-emitting devices, chemical and biological sensors, et al.. Design and synthesis of the materials with aggregation induced emission activity become one important research direction. We designed and synthesized a series of cyano-stilbene derivatives and study their optoelectronic properties. The main contents are concluded as follows:(1) It was reviewed on the recent development in the materials with aggregation induced emission. On the basis of which the new design idea was put forward in this dessertation.(2) The three compounds with D-π-A and two compounds with D-π-D models cyano-stilbene derivatives were synthesized by nucleophilic substitution, Vilsmeier reaction and Knoevenagel reaction so on. All the compounds were characterized by1H-NMR,13C-NMR, ESI. The crystal structures of Yl, Y2and Y3were determined by X-ray diffraction analysis. UV-Vis, fluorescence, AIE effect and electrochemical properties of the compounds were investigated systematically. The results showed that the maximum peaks of the fluorescence clearly show red-shift with increase of the polarity of solvents. The compounds Y1, Y2, Y3and Y5show strong fluorescent in the solid state but the weak intensity under the365nm UV lamp and its may have potential applications in the electroluminescent materials. The aggregation induced emission mechanism was elucidated based on the relationship between the structures and properties.(3) Two Schiff-base derivatives (Y6and Y7) were designed and synthesized, which were characterized by1H-NMR,13C-NMR and MALDI-TOF spectra. The absorption and fluorescence spectra were investigated. The results show that the maximum peaks of fluorescence clearly show red-shift with increase of the polarity of solvents; the nonradiation energy lossed and Stokes’ shift increased with the increase of polarity of the solvents. The electrochemical properties of compounds Y6and Y7were studied by cyclic voltammetry methods. According to the cyclic voltammetric curves and absorption spectra band gap, we calculated their frontier molecular orbital, HOMO and LUMO energy level. The compounds Y6and Y7show strong fluorescent in solid state but the weak intensity under the365nm UV lamp, and also can coordinate with metal ions. The materials may have potential applications in electroluminescent and ion recognition.