Synthesis And Properties Studies Of Chemical Doped Perylene Imide Derivatives

Perylene diimide derivative is a kind of heterocyclic hydrocarbon containing a nitrogen-oxygen hetero atom fused aromatic ring,which not only has excellent photothermal stability,but also has a low reduction potential,and is easily reduced by electricity or a reducing agent.It is a monovalent anion radical or a divalent anion.The peri-imide monovalent anion free gene has a high activity and characteristic near-infrared?NIR?absorption band which can participate in the free radical dimerization reaction and can be potentially applied in the field of photothermal therapy.At the same time,how to prepare the phthalimide dianion by simple mild conditions is a topic that needs to be explored.First,in the photothermal material,the phthalimide radical anion is an ideal organic photothermal preparation.Here,we prepared and confirmed two kinds of bay-substituted perylene imide monovalent radical anion salts,namely DBrPDI and TPPDI monovalent radical anion salts.Subsequently,the photothermal performance tests of the two free radical anion salts showed that the DBrPDI radical anion salt showed high photothermal performance in DMF solution,but decreased in aqueous solution.The TPPDI radical anion salt with a large sterically hindered group at the bay indicates that the chemical structure of the photothermal preparation can be adjusted to optimize and enhance the photothermal properties in aqueous solution.Secondly,we have found that the quinone imide monovalent radical anio n undergoes a free radical dimerization reaction at a high temperature for a long period of time to form a?-dimer of phthalimide(?-[DIPDI]₂^2-).The product was isolated by silica gel column chromatography,and its chemical structure was determined by NMR,COSE,MS,FT-IR,UV-Vis,FL,CV.The relationship between dimerization and temperature was studied by temperature-dependent ultraviolet and nuclear magnetic studies.Studies have shown that low temperature is beneficial to the generation of free radicals,and high temperature is beneficial to the formation of?-dimer.In addition,we have greatly reduced the reduction potential by introducing a strong electron withdrawing group at the bay of the imide,and then prepared and isolated the decanoyl group under mild conditions in the presence of DMF as a solvent and a reducing agent and K₂CO₃.The imine dianion salt was confirmed by a series of tests.Further studies have shown that it is stable in strong acid,organic alkaline and oxidizing environments,but unstable in inorganic alkaline environment.