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Selective Detection of Nerve Agent Simulants by Using Triarylmethanol‐Based Chromogenic Chemodosimeters
Author(s) -
Costero Ana M.,
Parra Margarita,
Gil Salvador,
Gotor Raúl,
MartínezMañez Ramón,
Sancenón Félix,
Royo Santiago
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200570
Subject(s) - chemistry , nerve agent , acetonitrile , soman , tabun , chromogenic , sarin , reagent , ether , organic chemistry , combinatorial chemistry , chromatography , enzyme , acetylcholinesterase
A family of triarylcarbinols 1 – 11 has been synthesised, and the chromogenic behaviour of the members in the presence of nerve‐agent simulants diethylcyanophosphonate (DCNP) and diisopropylfluorophosphate (DFP) in acetonitrile and in buffered mixed water/acetonitrile solutions has been investigated. Hydrophobic polyethylene oxide films of these compounds have been prepared. Some of these triarylcarbinols act as OFF/ON chemodosimeters for the nerve agent simulants. The sensing mechanism includes phosphorylation of the hydroxyl group in the triarylcarbinol derivatives, followed by a dephosphatation reaction induced by the electron‐donor groups present in the structure. The existence of additional tert ‐butyldimethylsilyl ether groups in compounds 2 and 3 permits these reagents to act as double probes by allowing selective signalling of DFP. The reactivity between 1 and 4 – 6 with DFP and DCNP in acetonitrile or water/acetonitrile solutions under pseudo first‐order kinetic conditions was studied to determine rate constants ( k ) and the half‐life times ( t 1/2 ) for the corresponding reactions. Films containing compound 2 were used to detect simulants both in solution and in the vapour phase. Finally, a logic device was designed that incorporated compounds 2 , 14 , and 15 that allowed detection of DFP (a Sarin and Soman simulant) and DCNP (a Tabun simulant), even in the presence of possible interferents such as acids.