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

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
(vD, 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.