Syntheses And Properties Of Discotic Aza-BODIPY,V-shaped Benzodithiophene And Ferrocene Derivatives

Liquid crystal is one of the important representatives of soft substances.It is an intermediate substance that has both crystal order and fluidity.Liquid crystals can be self-healing,responsive to environmental stimuli,and adaptable.They are an important class of smart materials.Multifunctional organic materials are receiving more and more attention,and it is an effective method to introduce functional groups into liquid crystal compounds to obtain multifunctional liquid crystal materials.Fluorescent compounds are one of the current research focuses in medicinal chemistry.Fluorescent compounds can be used as drug carriers,drug release and multifunctional drugs with imaging,targeting,and treatment.We introduced several fluorescent groups into the liquid crystalline mesogens,combining with the photophysical and ordering properties of liquid crystals,we hope to obtain nano-drug materials with liquid crystal properties and other excellent properties.Aza-BODIPY compounds and benzodithiophenes are fluorescent compounds with excellent photophysical properties,while ferrocene compounds have also excellent activities against malaria and cancer.Therefore,the introduction of these conjugated units into liquid crystal molecules could construct functional pharmaceutical liquid crystal compounds with complex self-assembled structures.The first chapter is based on the synthesis and properties of aza-BODIPY discoid molecules.In this chapter,two type of disc-like aza-BODIPY compound has been effectively prepared through a click reaction.First,the aza-BODIPY with alkoxy chain can self-assemble into a hexagonal columnar liquid crystal phase and a spherical organic gel.J aggregates were observed in its liquid crystal,gel,and solid states,while H aggregates were observed in its n-hexane solution.In addition,the compound and its previous intermediate 27 can be used as a chemical sensor for CN~-through a nucleophilic addition reaction,and the corresponding addition product can be doped with a blue dye to generate white light emission.This study provides a new method to obtain a new type of aza-BODIPY liquid crystal compound with CN~-detection and white light emission properties.The compound has strong emission in the near-infrared region,indicating that the compound has potential application in photothermal therapy.The excellent self-assembly and optoelectronic properties indicate that this columnar aza-BODIPY liquid crystal can be used as a multifunctional material in various aspects.In addition,the aza-BODIPY compound with PEO exhibites excellent water solubility,and can form micelles in water.The micelles show good encapsulation rate and drug loading rate towards podophyllotoxin,and have potential applications as drug loading materialsThe second chapter is based on the synthesis and properties of benzodithiophene pyridine V-shaped molecules.In this chapter,a novel V-shaped benzodithiophene-pyridine liquid crystal compound was synthesized by the Suzuki coupling reaction.This benzodithiophene-pyridine liquid crystalline mesogen can self-assemble into an unconventional hexagonal columnar liquid crystal phase.Each pillar of the pillar phase is composed of a tubular supramolecular structure.In addition,the compound can form an organic gel in a variety of organic solvents.And the morphology of the gel is related to the polarity of the solvent.This study provides a new method to obtain the desired supramolecular structure by controlling the polarity of the solvent.The photophysical properties of the compounds were studied.The A-D-A structure of the compounds imparted greatly Stokes shifts and solvent discoloration effects.Additionally,the terminal pyridine can further coordinate with platinum,indicating that this type of compound might have more profound applications as anticancer drugs.The excellent self-assembly and optoelectronic properties show that this columnar benzodithiophene-pyridine liquid crystal has great potential in many applications.The third chapter is based on the synthesis and properties of ferrocene molecules.In this chapter,α-cyano ferrocene compounds were synthesized using Knoevenagel condensation reaction and Suzukik reaction as key steps.None of the compounds containing three alkyl chains can self-assemble into liquid crystals.A compound containing one alkyl chain appears forming nematic liquid crystal phase.It is shown that the alkyl chain disturbs the assembly of the ferrocene liquid crystal compound.The compound containing three alkyl chains can form an organic gel having a spherical structure with a nano-petal shape in a n-butanol solvent,and the organic gel has a large specific surface area.This organic gel has potential applications in fields such as gas adsorption.The compound has been tested for antibacterial activity.The antibacterial activity of the compound is very low.To obtain a compound with high antibacterial activity,further modification of the structure of the compound is required.The fourth chapter is conclusions and innovationsThe fifth chapter is the experimental part,including detailed synthetic steps and spectrum data of the compounds.