3,4-Bis(3-tetrazolylfuroxan-4-yl)furoxan: A Linear C–C Bonded Pentaheterocyclic Energetic Material with High Heat of Formation and Superior Performance

[Image: see text] The design and preparation of new nitrogen-rich heterocyclic compounds are of considerable significance for the development of high-performing energetic materials. By combining nitrogen-rich tetrazole and oxygen-rich furoxan, a linear C–C bonded pentaheterocyclic energetic compound, 3,4-bis(3-tetrazolylfuroxan-4-yl) furoxan (BTTFO), was synthesized using a facile and straightforward method. Comprehensive X-ray analysis reveals the key role of hydrogen bonds, π–π interactions, and short contacts in the formation of dense packing of BTTFO and explains why a long chain-shaped molecule has a high density. This multicyclic structure incorporating three furoxan and two tetrazole moieties results in an exceptionally high heat of formation (1290.8 kJ mol(–1)) and favorable calculated detonation performances (v(D), 8621 m s(–1), P, 31.5 GPa). The interesting structure and fascinating properties demonstrated the feasibility of a linear multicyclic approach as a high-energy-density skeleton. Additionally, the thermodynamic parameters, electrostatic potential (ESP), and frontier molecular orbitals were also studied to get a better understanding of structure–property correlations.