The Synthesis, Characterization And Optical Properties Of Acrylonitrile Derivatives Based On Aggregation-Induced Emission Enhancement

The organic and macromolecule optical functional materials with aggregation-induced emission enhancement can regulate fluorescence intensity and wavelength by changing the molecular composition, twisted conformation, rigid structure, stacking morphology in aggregate or solid state. So these endow them wide application prospect in organic electroluminescence, organic solid state laser, fluorescent probe, bio imaging and many other high-tech field, which has been widespread concern and become an interdisciplinary filed emerging. Expanding design and synthesis of novel compounds with AIEE is currently one of the most important areas in organic photoelectric field research. For the sake of exploring new AIE-active organic or macromolecule materials, in this thesis, we synthesized and characterized two new kinds of acrylonitrile derivatives with AIEE characteristic, including indolo[3,2-b]carbazole-cored luminognes and novel cyanostillbene derivative and its initiated polymers. Subsequently, we fully studied the photophysical properties, the structure-activity relationship of these two kind materials and their application in LED devices. The main research contents are as follow:(1) The mechanism, and recent progress application and development prospect with AIE materials are reviewed. On the basis of these, the new design idea was put forward in this dissertation.(2) With indolo[3,2-b]carbazole as the core, a series of indolo[3,2-b]carbazole derivatives via Fischer, Vilsmeier, Knoevenagel, reduction action and so on, which were fully characterized by1H NMR,13C NMR, FT-IR, mass spectra and single crystal X-ray diffractions analysis.(3) The linear optical properties, electronic structure, thermal stability, electrochemical properties and morphology of aggregate of new indolo[3,2-b]carbazole derivatives (T1-T5) were system studied. The UV-Vis absorption spectra, fluorescence emission spectra studies showed that compound Tl, T2, T4possessed superior AIE-active. The crystal structure of T4indicated that the formation of J-aggregation and extension of the effective conjugation lengths commonly led to AIEE phenomenon. T2could excellently self assembly and be promising as an optical waveguide material in appropriate conditions, and lay the foundation for the optical waveguide material on its application in the future.(4) A novel cyanostillbene derivative (I) with symmetric hydroxyl is synthesized via a simple one step reaction, which is also utilized as the initiator to prepare and characterize poly(ε-caprolactone)(I-PCL) and poly(D, L-lactide)(I-PLA) via ring-opening polymerization (ROP). Target compound I exhibits superior aggregation-induced enhanced emission (AIEE) behavior in the mixed solvent of THF and water, which indicated that the AIEE fluorescence core I was anchored on a polymer chain, the luminogen aggregation of the initiator is well-realized and even enlarged after polymerization. The mechanism of AIEE for the system was finely explained by single crystal structure of initiator I and the framework of polymer itself. In view of higher thermal stability of polymer I-PLA, there had been attempts to use organic luminescence converters for light-emitting diode (LED) applications and obtain daylight white light.