Energy-Barrier-less Synthesis of Hexaaza-trifuranacyclopentadecaphane-hexaene\nat Ambient Temperature

A thermochemically\nstable furan-based hexaaza-trifuranacyclopentadecaphane-hexaene\n(AF-cpdp) as a π<sub>12</sub><sup>12</sup> cyclic-conjugated\ncolor enriched heterocycle has been synthesized at ambient temperature.\nAn energy-barrier-less (EBL) dehydrative azine formation of 2,5-diformylfuran\n(DFF) with hydrazine hydrate (N<sub>2</sub>H<sub>4</sub>·H<sub>2</sub>O) followed by a single-arm heteroconjugation and ring formation\nat the final step under classical and mechanochemical approaches,\navoiding external heating, was conducted for construction of a novel\nand highly stable cyclopentadecaphene (cpdp) conjugated system. The\ndeveloped protocol is simple, energy-efficient, atom-economical, and\neasy to scale-up.