New 2H-[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidine derivatives as luminescent fluorophores for detection of nitroaromatic explosives. / Verbitskiy, Egor V.; Gorbunov, Evgeny B.; Baranova, Anna A.; Lugovik, Kseniya I.; Khokhlov, Konstantin O.; Cheprakova, Ekaterina M.; Kim, Grigory A.; Rusinov, Gennady L.; Chupakhin, Oleg N.; Charushin, Valery N.
In: Tetrahedron, Vol. 72, No. 32, 01.01.2016, p. 4954-4961.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - New 2H-[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidine derivatives as luminescent fluorophores for detection of nitroaromatic explosives
AU - Verbitskiy, Egor V.
AU - Gorbunov, Evgeny B.
AU - Baranova, Anna A.
AU - Lugovik, Kseniya I.
AU - Khokhlov, Konstantin O.
AU - Cheprakova, Ekaterina M.
AU - Kim, Grigory A.
AU - Rusinov, Gennady L.
AU - Chupakhin, Oleg N.
AU - Charushin, Valery N.
PY - 2016/1/1
Y1 - 2016/1/1
N2 - A number of D–π–A type dyes on the basis of new 2H-[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidines, bearing various electron-donating carbazole and triphenylamine fragments, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that emission spectra of these compounds in acetonitrile are sensitive to the presence of nitroaromatic explosives, such as 2,4-dinitroanisole (DNAN), picric acid (PA), styphnic acid (SA), 1,3,5-triethoxy-2,4,6-trinitrobenzene (TETNB), 2,4-dinitrotoluene (DNT), 2,4,6-trinitrotoluene (TNT) and nitrobenzene (NB). Detection limits of fluorophores for DNAN, PA, SA, TETNB, DNT and TNT proved to be in the range from 4.82×10−1to 2.96×10−3mol/L, 2.10×10−3to 5.98×10−5mol/L, 1.26×10−1to 2.02×10−4mol/L, 1.58×10−1to 1.62×10−3mol/L, 1.26×10−1to 5.61×10−4mol/L and 9.01×10−2to 2.77×10−3mol/L, respectively. Selective fluorescence quenching response, including a sharp color change under UV irradiation (especially for PA, SA and DNT), makes these compounds promising fluorescence chemosensors for nitroaromatic explosives.
AB - A number of D–π–A type dyes on the basis of new 2H-[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidines, bearing various electron-donating carbazole and triphenylamine fragments, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that emission spectra of these compounds in acetonitrile are sensitive to the presence of nitroaromatic explosives, such as 2,4-dinitroanisole (DNAN), picric acid (PA), styphnic acid (SA), 1,3,5-triethoxy-2,4,6-trinitrobenzene (TETNB), 2,4-dinitrotoluene (DNT), 2,4,6-trinitrotoluene (TNT) and nitrobenzene (NB). Detection limits of fluorophores for DNAN, PA, SA, TETNB, DNT and TNT proved to be in the range from 4.82×10−1to 2.96×10−3mol/L, 2.10×10−3to 5.98×10−5mol/L, 1.26×10−1to 2.02×10−4mol/L, 1.58×10−1to 1.62×10−3mol/L, 1.26×10−1to 5.61×10−4mol/L and 9.01×10−2to 2.77×10−3mol/L, respectively. Selective fluorescence quenching response, including a sharp color change under UV irradiation (especially for PA, SA and DNT), makes these compounds promising fluorescence chemosensors for nitroaromatic explosives.
KW - Carbazole
KW - Fluorescence quenching
KW - Nitroaromatic explosives
KW - Pyrimidine
KW - Triphenylamine
UR - http://www.scopus.com/inward/record.url?scp=84978296039&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2016.06.071
DO - 10.1016/j.tet.2016.06.071
M3 - Article
AN - SCOPUS:84978296039
VL - 72
SP - 4954
EP - 4961
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 32
ER -
ID: 39451903