The Design, Synthesis And Property Of Fluorescent Organic Materials Based On BIM

Bisindolylmaleimides(BIM) such as Arcyriarubin A originally from natural products,have attracted much attention as promising red fluorescent materials, owing to their special structure such as non-planar and D-A system. Recently, lots of emissive organic materials based on BIM were disclosed. In this thesis, we designed and synthesized discrete BIM organic compounds, linear BIM polymer and cross-linked BIM polymer. In addition, we also studied the effects of molecular packing mode, polymer fixed effect and skeleton effect on the solid-state fluorescence of materials containing BIM.1. In order to study the effects of alkyl chain and molecular packing mode on fluorescent properties, BIM-based compounds M2-M6 were designed and synthesized by N-alkylation of BIM(M1). We studied the thermal and fluorescence properties of compounds M1-M6. Generally, with the introduction of dodecyl chain, the thermal stability of BIMs increased, while, Tg and Tm decreased. In addition, it's found that in diluted THF solution, compounds M2-M6 all display high fluoreseent quantum yield, while,in film state, compounds display low fluoreseent quantum yield except M5 and M6.Therefore, the effects of molecular packing mode on the solid-state fluorescence were investigated carefully. It's found that M5 and M6 in crystal state display a fluorescent quantum efficiency as high as 44.7% and 67.3%, which are higher than that in film state(26.4%, 8.1%) and powder(43.1%, 14.2%) respectively2. Two kinds of polymer that containing BIM were designed and synthesized by introducing BIM into the side chain of polynorbornene. The resulting polymers and compound were characterized by fourier transform infrared spectrometry, gel permeation chromatography, nuclear magnetic resonance, ultraviolet visible absorption spectra,photoluminescence spectrum and so on. The results show that in DMF solvent, compound M11, M12 display fluoreseent quantum efficiency as high as 41.5% and 53.9%, while,polymer PM9, PM10 give the value of 22.2% and 12.6%. In film state, compounds and polymer all tend to show a weak fluoreseent, but polymer PM10 still maintain fluorescent quantum efficiency as high as 1.5%. In addition, we also find that the the introduction of dodecyl chain make a good influence on fluoreseent quantum efficiency.3. The bisindolylmaleimides M14, M15 derived from BIM as well as their analogouscross-linked polymers PM14, PM15 were synthesized in high yield. Their chemical structures as well as properties were investigated by IR,13C-NMR, EA, PXRD and TGA.Although M14 and M15 gave a high photoluminescence quantum yield, its analogous cross-linked polymer PM14 and PM15 showed low quantum yield in solid state, possibly caused by close packing during the formation of cross-linked polymer.