One-step synthesis of a triangular donor/acceptor-accumulated compound with long-wavelength absorption

作者：Takahiro Oshima, Akiyuki Nakano, Kentaro Ikeda, Kan Wakamatsu, Tetsuo Iwanaga, Kiyoshi Fujisawa, Hideyuki Higashimura · 发表于：Chemistry Letters · 年份：2025 · DOI：10.1093/chemle/upaf173 · 被引用次数：1 · 研究领域：Crystal structures of chemical compounds、Structural and Chemical Analysis of Organic and Inorganic Compounds、Synthesis and Characterization of Heterocyclic Compounds

Abstract 1,6-Dihydro-7,12,13,18-hexaazatrinaphthylene (HATN–H2) was synthesized for the first time via a 1-step reaction of hexaketocyclohexane (HKC) with 1,2-phenylenediamine (PDA) above 130 °C, whereas well-known 1,6,7,12,13,18-hexaazatrinaphthylene was prepared at temperatures below 130 °C. The structure of HATN–H2 was determined via various analyses, and a quantitative yield was achieved when a large excess of PDA to HKC was used in the absence of solvents. HATN–H2 exhibited long-wavelength absorption at 667 nm, which was attributed to the compact triangular structure comprising 1 electron-donating amino group and 2 electron-withdrawing imino groups.