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

ABSTRACT: 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, ?-? 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.

SUBMITTER: Zhai L 

PROVIDER: S-EPMC7241007 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature