Towards the fluorogenic detection of peroxide explosives through host-guest chemistry

Abstract

[EN] Two dansyl-modified beta-cyclodextrin derivatives (1 and 2) have been synthesized as host-guest sensory systems for the direct fluorescent detection of the peroxide explosives diacetone diperoxide (DADP) and triacetone triperoxide (TATP) in aqueous media. The sensing is based on the displacement of the dansyl moiety from the cavity of the cyclodextrin by the peroxide guest resulting in a decrease of the intensity of the fluorescence of the dye. Both systems showed similar fluorescent responses and were more sensitive towards TATP than DADP. ; We thank the Spanish Government (MAT2015-64139-C4-4-R) and Generalitat Valenciana (PROMETEOII/2014/047) for financial support. ; Almenar, E.; Costero, AM.; Gaviña, P.; Gil Grau, S.; Parra Álvarez, M. (2018). Towards the fluorogenic detection of peroxide explosives through host-guest chemistry. Royal Society Open Science. 5(4). https://doi.org/10.1098/rsos.171787 ; S ; 5 ; 4 ; Dubnikova, F., Kosloff, R., Almog, J., Zeiri, Y., Boese, R., Itzhaky, H., … Keinan, E. (2005). Decomposition of Triacetone Triperoxide Is an Entropic Explosion. Journal of the American Chemical Society, 127(4), 1146-1159. doi:10.1021/ja0464903 ; Fitzgerald, M., & Bilusich, D. (2011). Sulfuric, Hydrochloric, and Nitric Acid-Catalyzed Triacetone Triperoxide (TATP) Reaction Mixtures: An Aging Study. Journal of Forensic Sciences, 56(5), 1143-1149. doi:10.1111/j.1556-4029.2011.01806.x ; Matyáš, R., Pachman, J., & Ang, H.-G. (2009). Study of TATP: Spontaneous Transformation of TATP to DADP - Full Paper. Propellants, Explosives, Pyrotechnics, 34(6), 484-488. doi:10.1002/prep.200800043 ; Matyas, R., Pachman, J., & Ang, H.-G. (2008). Study of TATP: Spontaneous Transformation of TATP to DADP. Propellants, Explosives, Pyrotechnics, 33(2), 89-91. doi:10.1002/prep.200700247 ; Wang, J. (2007). Electrochemical Sensing of Explosives. Electroanalysis, 19(4), 415-423. doi:10.1002/elan.200603748 ; Bauer, C., Willer, U., Lewicki, R., Pohlkötter, A., Kosterev, A., Kosynkin, D., … Schade, W. (2009). A ...