Synthesis Of Two Special Fused Ring Compounds

In the 1970s,by doping iodine into polyacetylene,Prof.A.J.Heeger synthesized the conductive polymers successfully,which broke through the common sense that the organic materials are insulators.Alternative single and double bond structures orπ-conjugated structures are required for organics to be conductive.Polycyclic aromatic hydrocarbons have drawn scientists’attentions.Polycyclic aromatic hydrocarbons have unique chemical structures and electronic structures and thus have great importance in the application of organic photoelectric materials.In this thesis,two special types of polycyclic aromatic hydrocarbons are designed and synthesized specifically.In the first part,a class of polycyclic aromatic hydrocarbon compounds which can be used in organic photovoltaic cells are constructed successfully.The application of intermolecular singlet fission materials in organic solar cells are limited by molecular packing and the morphology of the active layer.Therefore,non-fullerene acceptor molecular with intramolecular singlet fission properties by combining pentacene,singlet fission model molecule,with perylene diimide,one of the best acceptors were synthesized.The two key steps are the Suzuki-Miyaura coupling reaction and Katz modified Mallory photocyclization reaction,respectively.Finally,DFT calculations demostrated the singlet fission properties of these compounds.In the second part,two steps of Barton-Kellogg reaction and Katz modified Mallory photocyclization reaction have been used to obtain mono-and di-fluorine-substituted c-HBC molecules,and then microwaves were used to build a five-membered ring in the presence ofγ-Al₂O₃.The results showed that the microwave reaction can activate the C-F bond on the bay region of polycyclic aromatic hydrocarbons in the presence ofγ-Al₂O₃.In the following experiments,a five-membered ring in polycyclic aromatic hydrocarbons is expected to be obtain,which has a profound effect on organic synthesis strategy of carbon nanotubes.These two design concepts enriched the organic synthesis methods of polycyclic aromatic hydrocarbons and gave a better understanding of the organic synthesis of polycyclic aromatic hydrocarbons with specific structures and properties.