Synthesis And Properties Of Carbohydrate Modified Bi-perylene Monoimide Derivatives

Fluorescence-based techniques have the advantages of simple operation,fast response,high signal-to-noise ratio and high sensitivity.Therefore,various types of fluorescent dyes have been developed.Fluorescent dyes are used in a broad field due to their optical stability,non-invasive treatment,cell compatibility,and realtime response.In addition,fluorescent dyes displaying large Stokes shifts are most widely adopted,as they can minimize severe crosstalk between excitation and emission spectra,improve fluorescence signal-to-noise ratio,and reduce self-quenching effectively.Bi-perylene monoimide derivatives exhibited exceptional photochemical stability,high fluorescence quantum yields,and large Stokes shifts.However,bi-perylene monoimide derivatives suffer from poor water-solubility,which limited their applications in biological fields.On the other hand,lactose moiety has good water-solubility and excellent biocompatibility.Significantly,lactose displays high selectivity to carbohydrate receptor on the cell surface.In this paper,glycodendrimer modified bi-perylene monoimidederivatives were designed and synthesized.Their self-assembly behaviour,optical properties and fluorescence imaging were investigated.The contents are as follows:Bi-perylene monoimide compounds were synthesized through Suzuki coupling reaction and Click reaction under the condentions of Pd-catalyzed and cuprous ion.These compounds was fully characterized by ¹H NMR?¹³C NMR and HRMS.The self-assembly properties of DiPMI-18Lac and DiPMI-9Lac were studied by concentration,solvent and temperature-dependent spectra.DiPMI-18Lac and DiPMI-9Lac showed the maximum absorption and emission bands at 540 nm and 720 nm,respectively.it is interestingly found that DiPMI-18Lac and DiPMI-9Lac showed cooling induced emission enhancement in aqueous solution and in the solid state.The mechanism was due to the inhibition of electronic transfer process between the perylene monoimide bancebone linked by the C-C bond.Furthermore,the binding interactions of DiPMI-18Lac and DiPMI-9Lac with lectins were investigated.DiPMI-18Lac and DiPMI-9Lac showed selectively interactions with peanut agglutinin?PNA?lectin.In addition,DiPMI-18Lac and DiPMI-9Lac exhibited fluorescence imaging with HepG2 cells through ASGP-R receptor.