The invention discloses a large-pi conjugated
phosphorus-doped fused ring compound as well as a preparation method and application thereof, and belongs to the technical field of
organic synthesis. The preparation method comprises the following steps: by adopting a series strategy of combining visible light
catalysis and
acid treatment, carrying out dehydrophosphine
free radical addition / cyclization reaction on commercially available bicycloolefin and a secondary
phosphine oxide compound serving as raw materials under the
irradiation of visible light in the presence of
cobalt oxime complex
catalysis and organic alkali to generate a
phosphorus heterocyclic intermediate; then the intermediate is heated and refluxed in concentrated
hydrochloric acid for deoxidation
aromatization, and large-pi conjugated
phosphorus-doped condensed ring structures such as
naphthalene ring benzo-phosphorus
cyclopentadiene are efficiently constructed. The method provided by the invention overcomes the defects of tedious steps and large substrate limitation of the traditional
alkyne route, has the advantages of mild
reaction conditions, simple operation, good to excellent yield (up to 70-90%), and realization of one-pot synthesis, and is suitable for large-scale production. A series of prepared novel phosphorus-doped fused ring compounds show strong
fluorescence under
ultraviolet irradiation, and have application potential in the field of organic photoelectric materials.