This application discloses a negative curvature
polycyclic aromatic hydrocarbon containing an eight-membered ring, its synthesis method, and its application, belonging to the field of
organic synthesis. The synthesis method uses a haloacenaphthene derivative as a starting material. First, a tetrahalogenated key intermediate containing an eight-membered ring is constructed via a
titanium tetrachloride-catalyzed cyclization tetramerization reaction. Subsequently, this intermediate undergoes a cyclization
coupling reaction with an
alkyne compound in the presence of a
palladium catalyst, silver salt, and
phosphine ligand to generate a negative curvature
polycyclic aromatic hydrocarbon containing an eight-membered ring. The synthesis method of this application avoids multi-step precursor synthesis, resulting in a concise process. It allows for the flexible introduction of functional groups such as
trifluoromethyl and silyl groups, improving the
solubility and processability of the material. The obtained product exhibits a non-planar configuration, a narrow optical
band gap, and excellent
electron transport properties, making it suitable for applications... n Applications include semiconductors, chiral
optoelectronic materials, and nano-carbon materials.