Zobrazit minimální záznam
dc.contributor.author |
Dey, Nilanjan
|
|
dc.contributor.author |
Kulhánek, Jiří
|
|
dc.contributor.author |
Bureš, Filip
|
|
dc.contributor.author |
Bhattacharya, Santanu
|
|
dc.date.accessioned |
2022-06-03T12:33:35Z |
|
dc.date.available |
2022-06-03T12:33:35Z |
|
dc.date.issued |
2021 |
|
dc.identifier.issn |
0022-3263 |
|
dc.identifier.uri |
https://hdl.handle.net/10195/79363 |
|
dc.description.abstract |
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. |
eng |
dc.format |
p. 14663-14671 |
eng |
dc.language.iso |
eng |
|
dc.publisher |
American Chemical Society |
eng |
dc.relation.ispartof |
Journal of Organic Chemistry, volume 86, issue: 21 |
eng |
dc.rights |
Článek ve verzi „published“ je přístupný pouze v rámci univerzity. |
cze |
dc.subject |
imidazole |
eng |
dc.subject |
push-pull dye |
eng |
dc.subject |
nerve agent |
eng |
dc.subject |
catalyst |
eng |
dc.subject |
detoxification |
eng |
dc.subject |
imidazol |
cze |
dc.subject |
push-pull barvivo |
cze |
dc.subject |
nervová látka |
cze |
dc.subject |
katalyzátor |
cze |
dc.subject |
detoxikace |
cze |
dc.title |
Imidazole-Functionalized Y-Shaped Push-Pull Dye for Nerve Agent Sensing as well as a Catalyst for Their Detoxification |
eng |
dc.title.alternative |
Push-pull barvivo tvaru Y na bázi imidazolu jako detektor nervových látek a rovněž jako katalyzátor jejich detoxikace |
cze |
dc.type |
article |
eng |
dc.description.abstract-translated |
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. |
cze |
dc.peerreviewed |
yes |
eng |
dc.publicationstatus |
published version |
eng |
dc.identifier.doi |
10.1021/acs.joc.1c01488 |
|
dc.relation.publisherversion |
https://pubs.acs.org/doi/10.1021/acs.joc.1c01488 |
|
dc.identifier.wos |
000716778300032 |
|
dc.identifier.scopus |
2-s2.0-85118171951 |
|
dc.identifier.obd |
39886405 |
|
Tento záznam se objevuje v následujících kolekcích
Zobrazit minimální záznam
|
Vyhledávání
Procházet
-
Vše v Digitální knihovně
-
Tato kolekce
Můj účet
|