In our rapidly advancing world, there is increasing need in the field of security and national defense for better and accurate mechanisms for detecting both aromatic and non-aromatic explosives. In this project, we have utilized density functional theory to establish relative binding interaction energies between halogen-containing sensor molecules and nitro-containing explosives. The halogen-containing sensor molecules studied include: diiodobenzene, diiodotetrafluorobenzene, dibromobenzene, dibromotetrafluorobenzene, dichlorobenzene and dichlorotetrafluorobenzene. All geometries obtained correspond to minima on the potential energy surface with the sigma hole on the halogen aligned with a lone pair of electrons on the nitro-moiety of the explosive. Our results show that the strongest interactions occur with sensors that contain iodine due to iodine’s large atomic size, high polarization and smallest electronegativity compared to other halogens studied. To test our results experimentally, we synthetically designed halo based sensors using 1,4-dihalobenzene (X=Cl, Br and I) with and without tetra-fluoro electron withdrawing groups attached to the benzene ring. We then used these sensors to measure the interaction responses to explosive model compounds cyclohexanone and dimethyl-dinitro-benzene in nitrogen gas.<br/><br/><br/><br/>

Halogen bonding as a mechanism for aromatic and non-aromatic explosive detection

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.