Design Synthesis And Properties Of Perylene Diimides Organic Low Molecules Substituted In Different Positions

Perylene diimides were first discovered and synthesized successfully in 1912.They were used as a red dye in 1913 in the field of vat dyes.In 1950,they developed into the field of organic pigments.The researchers believe that it is one of the very promising n-type semiconductor electron acceptor materials,and the development prospect is very broad.Perylene diimides have good thermal stability and excellent photochemistry and physical properties,very high fluorescence quantum efficiency(even close to 100%),excellent carrier mobility,and strong reduction potential,so they are reduced dyes,laser dyes,fluorescent probes,organic light-emitting diodes,field-effect transistors,organic solar cells,etc.have been deeply studied and widely used in many directions.In this thesis,we design functional modifications at the bay position and nonbay position of perylene diimides,and synthesize a series of differently substituted perylene diimides.By comparing these special perylene diimides to explore the relationship between the molecular structure of different Perylene diimides and their photoelectric properties.This paper mainly includes the following parts:The first chapter summarizes the development history,unique structure,good properties,common synthesis methods and wide application of perylene diimides compounds and their derivatives,as well as the shortcomings in the development process.The practical application and future development of perylene diimides compounds in the field of organic semiconductor materials are mainly introduced.The second chapter introduces in detail the functional modification of 1,6,7,12 positions of perylene diimides.By using 3,4,9,10-perylenetetracarboxylic dianhydride as the raw material,a series of perylene diimides compounds with different substituents in the bay position were synthesized by introducing different substituent groups in the PDI bay position method.To study and compare the effects of different substituents on the properties of perylene diimides compounds,focusing on the influence on the photoelectric properties of perylene diimides compounds.From this,we explored that the LUMO level of compound 8 substituted by phenylsulfone reached a record-breaking-4.75 eV.In addition,the maximum emission ranged from 540 to 692 nm.The third chapter introduces the method of functional modification of 2,5,8,11 positions of perylene diimides compounds in detail.Similarly,3,4,9,10-perylenetetracarboxylic dianhydride was first used as the raw material to introduce different substituent groups in the nonbay position.It is particularly worth noting that eventually free radicals will be introduced into the nonbay position of PDI to achieve functional modification of perylene diimides compounds and study the characteristics of this compound.We expect that after the four phosphine groups enter the nonbay position of PDI,the unique electronic characteristics will greatly enhance the stability of the PDI system and the PDI radical ion,and will open up a deeper exploration of perylene diimides compounds world and wider application potential.The fourth chapter summarizes the thesis and looks forward to the problems in the research field and the future development prospects.