Synthesis Of Stable Triphenyltripentene Chiral Triradical And Thiadiazole-contained Carbon Diradical

This thesis mainly studies the synthesis of chiral triradical based on tribenzotriquinacene(TBTQ)and thiadiazole-contained carbon diradical.And the synthesis and properties of fluorescent molecules are studied.The full text includes four chapters.The first chapter provides an overview of stable free radicals.In the second chapter,two kinds of compounds,chiral TBTQ tri-tetrazine radical and tri-Blatter radical,were designed with the known chiral TBTQ as the core,and the synthetic route was explored.First,the radical precursor compounds were synthesized by condensation reaction with the synthesized mixture carbohydrazide compound and TBTQ trialdehyde(C₁ and C₃ configuration),and the separation of C₁and C₃ configuration was successfully achieved.The C₁ configuration TBTQ tri-tetrazine radical was synthesized from the precursor compound,which indicates that the synthetic route was completed.At the same time,the optical resolution method of TBTQ trialdehyde has been improved,and sufficient chiral TBTQ trialdehyde is being accumulated to synthesize chiral TBTQ tri-tetrazine radical by the route above.Secondly,TBTQ triamines with C₁ and C₃ configurations were synthesized,isolated and purified,and the synthetic route of TBTQ tri-Blatter radical was explored using TBTQ triamine with C₁ configuration as raw materials.In the third chapter,benzoindene diradicals were designed by calculation,and the diradical character and stability of diradical compounds was improved by introducing electron-deficient heterocyclic thiadiazoles.And synthetic exploration was carried out through multiple routes.First,the synthesis of diradical precursor compound 3-9 was completed by using 4-bromo-5-methyl-1,2-phenylenediamine as raw material,and the synthesis of diradical compounds is still being explored.Secondly,the diradical precursor diol compounds containing naphthalene ring were successfully synthesized by using methyl 3-hydroxy-2-naphthoate as the raw material,and an attempt was made to synthesize a naphthindene diradical compounds 3-2a and 3-2b.However,they are not stable enough and their stability is being improved by adjusting the substituents.In chapter four,a series of anilinoanthracene derivatives were synthesized by a concise route,and their single crystal structures were successfully obtained for the study of structure-activity relationship.At the same time,the study of photophysical properties and the testing of undoped pure organic OLED devices were carried out.Compound 4-3 has better luminous efficiency than others,and the maximum external quantum efficiency(EQE)could reach 4.1%.The research work in this thesis not only provides a new idea for the design and synthesis of stable chiral open-shell organic triradical compounds;but also provides a new method for the separation and optical resolution of TBTQ trialdehyde mixtures,which will contribute to the further development of TBTQ and its derivatives.