Reaction Of PAHs Containing O-quinone Structure With Indole And Physicochemical Properties Of The Products

Organic functional materials are stacked "top-down" through intermolecular interaction,the geometric configuration、assembly trend and electronic structure of molecular have become important influencing factors to Organic functional material properties.However,As the main building block of organic functional materials,polycyclic aromatic hydrocarbons(PAHs)exhibit excellent photoelectric performance,were used in the preparation of organic optoelectronic functional materials and light and flexible electronic devices.We can regulate photoelectric properties of material through various chemical modifications.The central skeleton of trichalcogensumanene is curved,It contains thiophene cyclos and alkoxy groups and have a π electronic system.With the properties of rich electron and ring tension,the peripheral alkoxy groups of trichalcogensumanene can be selectively oxidized to o-quinone structures.As an active functional group,the introduction of carbonyl groups provides reactive sites and multiple possibilities for subsequent functionalized extension,and this structure can be used as substrate for a variety of reaction and compound extension.In this paper,polycyclic aromatic hydrocarbon compounds containing o-quinone structures were selected to react with 1,3-dipole indole to construct polycyclic compounds with diverse functions.Chapter 1: Research Background and design rationale.Firstly,We made a brief introduction about the background of PAHs.We next reviewed the synthesis and development process of corannulene and sumanene,then we emphasized the functionalization and extension of chalcogenide hybrid polycyclic aromatic hydrocarbo-ns.Finally,the design of this thesis is proposed.Chapter 2: Design synthesis and crystal structure study of indole-furan fused triselenasumanene.In this chapter,we combined selenasumanene containing o-quinone with indole structure.At the same time,we analyzed the chemical structure of the main and by-products.By deeply optimizing the reaction conditions,we synthesized a series of indole-furan fused selenium heteroxylinene and resolved the crystal structure of the compounds.Chapter 3: Study on the properties of indole-furan fused triselenasumanene.Based on theoretical calculations,spectroscopy and electrochemistry,the electronic structure of such compounds was systematically studied.Due to the amplification of the conjugated system,the HOMO-LUMO gap of these compounds narrowed,showing a significantly redshifted absorption band.Due to their obvious electron-rich characteristics,they form radical positive ions through intermolecular charge transfer under acidification or the presence of electron-oxidants,showing obvious absorption redshift and ESR signals.Chapter 4: Design synthesis and performance study of PAHs molecules containing di-indole structure.In this chapter,a PAHs imide containing o-quinone structure combined with indole fragments.After the nucleophilic addition of indole to o-quinone structural units and the rearrangement of indole,a pair of polycyclic aromatic hydrocarbon imide isomers containing di-indole structure were obtained.In addition,the crystal structure exploration,theoretical calculation and spectral test analysis of the isomers show that there are great differences between the isomers in UV-Vis absorption spectrum and fluorescence emission spectrum.Chapter 5: Summary and outlook.We summarized the work during the master’s period,pointed out the shortcomings and put forward the next work plan.