Synthesis of oligoacenes using precursors for evaluation of their electronic structures.

Acenes, which are hydrocarbons comprising linearly fused benzene rings, have attracted considerable attention owing to their electronic structures and utility as organic electronic materials. However, the ease with which oligoacenes undergo oxidation increases with the number of linearly fused benzene rings owing to the increased energy of the highest occupied molecular orbital. The synthesis of naked oligoacenes with seven or more benzene rings is difficult because their open-shell structure renders them unstable. The recent development of a precursor method has enabled the in situ synthesis of oligoacenes under specific conditions and the spectroscopic observation of oligoacene in single crystals, in film matrices and under cryogenic conditions. Scanning tunneling microscopy and non-contact atomic force microscopy under ultra-high vacuum conditions have also made significant advances in the study of oligoacenes and oligoazaacenes. This paper reviews the recent progress in the synthesis of oligoacenes using precursors, with a particular focus on the chemical structures, synthesis, and reactivity of the precursors. The electronic properties of oligoacenes are also discussed in relation to the number of fused benzene rings, including their energy levels and spin states. These results will contribute to the synthesis and development of carbon nanomaterials with applications in the field of organic electronics.