Synthesis Of Water-soluble Perylene Bisimide And DPP Derivatives And Their Functionalization

Organic fluorescent dyes are widely used in solar cells,biological probes and imaging,and solid-state fluorescent materials,because of their potent optical properties.However,most of the organic fluorescent dyes have poor water solubility,which limited their use in the biological field,so improving the water solubility of fluorescent dyes is of great importance.Perylene bisimides and Diketopyrrolopyrrole(DPP)derivatives possessed excellent photo-thermal stability,and showed high fluorescent quantum efficiency.In recently years,water-soluble perylene bisimide and DPP derivatives modified by cyclodextrins,ether chains,carbohydrates and crown ethers had been widely investigated.Among them,carbohydrates and ether chain derivatives exhibited good biocompatibility and unique specifical recognition with the glycoprotein on the cell.On the other hand,ether chain derivatives are drug carrier,which can effectively reduce the toxicity of drugs.Based on the above analysis,water-soluble perylene bisimide derivative PBI-2Lac-DPA with carbohydrate conjugates was synthesized.Its application in the fluorescence sensing of Cd2+ ion was studied,showed selectively recognition with Cd2+ ion and showed fluorescence imaging with Hep G2 cells.1)Alkynyl-modified perylene bisimide intermediates were synthesized by condensation reaction of thtrachloroperone anhydride with propargylamine,then the mono-substituted derivative of perylene bisimide on the bays was prepared And then,PBI-5 reacted with dipyridylmethylamine(DPA),further reacted with lactose derivative through click reaction.The targeted compound PBI-2Lac-DPA was obtained by removing the acety group.Compounds PBI-2Lac-DPA and intermedates were characterized by 1H NMR,13 C NMR and HRMS.The optical characteristics of compound PBI-2Lac-DPA were investigated at different p H values,which indicated that compound PBI-2Lac-DPA was less affected between the p H value 4 and 9.The selective recognition of PBI-2Lac-DPA for different metal ions(Ba2+?Ca2+?Co2+?K+?Mg2+?Mn2+?Ni2+?Zn2+? Cd2+)was studied by fluorescence spectra.It was interesting found that PBI-2Lac-DPA showed a highly selective identification of cadmiumions,and exhibited fluorescence imaging with Hep G2 cells through recognization of the ASGP receptors on Hep G2 cells.2)Compounds DPP-EN modified by triethylene glycol monomethyl ether,DPP-Lac modified by lactose and DPPMal modified by Maltotriose were synthesized.Compound DPPMal showed C—C single bond controlled optical properties,exhibited fluorescence imaging with MCF-7 cells.