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Imidazole-Functionalized Y-Shaped Push-Pull Dye for Nerve Agent Sensing as well as a Catalyst for Their Detoxification
Authors: Dey Nilanjan | Kulhánek Jiří | Bureš Filip | Bhattacharya Santanu
Year: 2021
Type of publication: článek v odborném periodiku
Name of source: Journal of Organic Chemistry
Publisher name: American Chemical Society
Place: Washington
Page from-to: 14663-14671
Titles:
Language Name Abstract Keywords
cze Push-pull barvivo tvaru Y na bázi imidazolu jako detektor nervových látek a rovněž jako katalyzátor jejich detoxikace Bylo připraveno push-pull barvivo tvaru písmene Y na bázi imidazolu a pi-konjugovaného řetězce nesoucí N,N-dimethylanilino donor a benzonitrilový akceptor. V roztoku vykazuje žlutou barvu díky rozáhlé charge-transfer interakci, ovšem fluorescence u něho nebyla pozorována. Přidání nervové látky jako diethyl-chlorfosfát nebo diethyl-kyanfosfát způsobuje modrou fluorescenci. Mechanistické studie ukázaly na nukleofilní atak imidazolu na atom fosforu vedoucí k tvorbě fosforylovaného meziproduktu, který ve vodném prostředí podléhá hydrolýze. imidazol; push-pull barvivo; nervová látka; katalyzátor; detoxikace
eng Imidazole-Functionalized Y-Shaped Push-Pull Dye for Nerve Agent Sensing as well as a Catalyst for Their Detoxification A Y-shaped push-pull dye (1) with N,N-dimethylanilino donors and a benzonitrile acceptor connected via an imidazole-based Jr-conjugated spacer was designed. It showed a dark yellow color in solution due to facile intramolecular charge-transfer interaction, but no fluorescence was detected, presumably due to the photo-induced electron transfer effect of the imidazole moiety. However, addition of nerve agents such as diethyl chlorophosphate (DCP, sarin mimic) and diethyl cyanophosphate (DCNP, Tabun mimic) resulted in a blue-colored fluorescence with fading of the native dark yellow color. Mechanistic studies indicated nucleophilic attack of imidazole at the phosphorus of DCP or DCNP, leading to the formation of a phosphorylated intermediate, which undergoes time-dependent hydrolysis (similar to 24 h) in aqueous medium. This process recovers the free probe (enzyme-like behavior) and releases a less-toxic organophosphate compound as the byproduct. The phosphorylated derivative of 1, formed during such interaction, shows a different electronic behavior, which reduces the extent of charge-transfer interaction as well as nonradiative decay and supports emissive properties. Considering the high sensitivity of 1 towards DCP and DCNP with LOD 35 and 42 ppb, we prepared easy test strips for on-site vapor-phase detection of nerve agents. Imidazole; Push-Pull Dye; Nerve Agent; Catalyst; Detoxification

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