Synthesis Of Perylene Diimide Derivatives And Their Applications In Optoelectronic And Fluorescent Analysis

There are many types of perylene diimide derivatives.Its core is composed of five benzene rings and contains a large?-?conjugate plane.Substituting different positions of the PDI with the same substituent or replacing the same position of the PDI with different substituents will have a huge impact on its properties.By combining PDI units with multiple functional group substituents in one molecule,compounds with novel optoelectronic properties can be obtained.The conjugate structure of the core part of the PDI molecule makes the electrons in the molecule be delocalized.Thus,the polarizability of the electron cloud is very high,resuting high fluorescence quantum yield,light stability,thermal stability,chemical inertness and wide absorption spectrum.Based on these properties,three simple PDIs were synthesized in this thesis,and photoelectric sensors and fluorescence sensors were constructed for their application in the detection of dopamine hydrochloride?DA?,ascorbic acid?AA?and common trivalent ions.Paper content includes:1.A rod-shaped dimethyl PDI?DPDI?,a fibrous carboxyl PDI?CPDI?and a two-dimensional pleated layered amino PDI?APDI?were synthesized,and their photoelectric properties were compared.An amino PDI with good photoelectric properties was selected and used as a photosensitive material to construct a photoelectric sensor for the detection of DA.2.The two-dimensional fold-layered amino APDI has good photoelectric properties.When the surface is modified by cobalt oxyhydroxide?CoOOH?,its photoelectric properties will be declined.After the addition of AA,the photoelectric properties could be restored.Based on this,this experiment demonstrated for the first time the preparation of optoelectronic APDI materials using CoOOH nanosheets as attenuators.And use it to build a photoelectric sensor for quantitative detection of AA3.APDI has two fluorescence emission peaks at 549 nm and 598 nm(F₅₄₉ and F₅₉₈).However,when its surface is modified by CoOOH,the fluorescence performance of amino PDI is effectively quenched by CoOOH.When AA was added,the fluorescence properties of CoOOH-modified APDI were restored.The fluorescence intensity ratio(F₅₄₉/F₅₉₈)was positively correlated with the concentration of AA.Therefore,the ratio-type fluorescence sensor constructed with CoOOH modified APDI can be used for quantitative detection of AA.4.Fibrous DPDI has strong fluorescence emission peaks at 555 nm and 598 nm(F₅₅₅ and F₅₉₈).It is found that when trivalent ions(Fe³⁺,Cr³⁺,Al³⁺)are added,the ratio response of F₅₉₈/F₅₅₅ could be enhanced with the increased of concentration of ion.Based on this property,a ratiometric fluorescence sensor can be developed for the detection of trivalent metal ions.Moreover,when NaOH solution is added,the ratio response of F₅₉₈/F₅₅₅ of DPDI will be restored.The recognition of trivalent ions by DPDI is reversible.Based on this,this experiment can also be used for the ratio detection of pH.