Construction Of Functional Supramolecular Systems Based On BODIPY Fluorescent Dyes And Their Potential Applications

Boron-dipyrrolemethene(BODIPY)is a new kind of fluorescent dye,which is composed of complexed with a disubstituted atom,typically a BF2 unit in the center and two pyrrole rings on each side,having very good conjugate planar structure,where the two fluorine atoms are linked together by one boron atom and have a symmetrical distribution in the BODIPY plane.BODIPY dyes have very excellent optical properties,such as high excitation coefficients,sharp fluorescence peaks with high fluorescence quantum yields,and high stability against light,so they are relatively insensitive to the polarity and pH of their environment,and small modifications to their structures which enable fine tuning of their fluorescence characteristics.Therefore,due to its special structure and excellent advantages,BODIPY dyes have been widely used as labeling reagents,fluorescent switches,chemosensors,anti-cancer drugs,photosensitive reagent,and laser dyes,and it attract interests of more and more supramolecular chemistry researchers.In this dissertation,we have constructed a novel supramolecular system based on functional BODIPY derivatives,and also made a series of synthetic exploration work.This thesis mainly includes the following two parts:In chapter 1,we designed and synthesized BODIPY derivative G1 as the guest molecule and constructed the supramolecular vesicles with the water-soluble pillar[5]arene driven by the host-guest interactions.Chemotherapic drug DOX is successfully encapsulated into these vesicles.In this point,G1 plays a dual role,acting not only as a guest molecule but also as a photosensitizer for photodynamic therapy.Therefore,this is the first example of pillar[n]arene-based drug delivery system for chemo-and photodynamic therapies.In chapter 2,we designed a symmetric BODIPY-based diselenides,which combined the light physical properties and redox advantages together.After many failures experiments,we have successfully designed and prepared a bola-type diselenide guest G2,assume it can be used to further develop novel supramolecular drug delivery systems.Follow-up research work is currently underway.