Imine-functionalized, turn-on fluorophore for DCP

Abstract A monopyrene-imine derivative 1 is a highly selective and sensitive “turn-on” fluorogenic probe for diethyl chlorophosphate (DCP), a stimulant for organophosphorus nerve agents. Upon addition of DCP to a solution of 1 , a phosphoramidate was formed which exhibited an enhanced fluorescence emission at 425 nm. When exposed to DCP in the vapor phase, 1 impregnated on silica gel showed a sky-blue fluorescence.

[1]  X. Qian,et al.  Detecting Hg2+ ions with an ICT fluorescent sensor molecule: remarkable emission spectra shift and unique selectivity. , 2006, The Journal of organic chemistry.

[2]  William S. Augerson.  Chemical and Biological Warfare Agents , 2001 .

[3]  Joseph Epstein,et al.  Reaction for Colorimetric Estimation of Some Phosphorous Compounds , 1957 .

[4]  Akimitsu Okamoto,et al.  Pyrene-labeled oligodeoxynucleotide probe for detecting base insertion by excimer fluorescence emission. , 2004, Journal of the American Chemical Society.

[5]  D R Walt,et al.  Biological warfare detection. , 2000, Analytical chemistry.

[6]  W. Stigelman,et al.  Goodman and Gilman's the Pharmacological Basis of Therapeutics , 1986 .

[7]  J. Lee,et al.  An excimer-based, binuclear, on-off switchable calix[4]crown chemosensor. , 2004, Journal of the American Chemical Society.

[8]  T. Novak,et al.  Decomposition at 90.degree.C of the cholinesterase substrate indoxyl acetate impregnated on paper supports , 1979 .

[9]  Bernard. Gehauf,et al.  Detection and Estimation of Nerve Gases by Fluorescence Reaction , 1957 .

[10]  Kelly A. Van Houten,et al.  Rapid Luminescent Detection of Phosphate Esters in Solution and the Gas Phase Using (dppe)Pt{S2C2(2-pyridyl)(CH2CH2OH)} , 1998 .

[11]  Yi Xiao,et al.  Ratiometric and selective fluorescent sensor for CuII based on internal charge transfer (ICT). , 2005, Organic letters.

[12]  Fang Wang,et al.  Fluorescence turn on of coumarin derivatives by metal cations: a new signaling mechanism based on C=N isomerization. , 2007, Organic letters.

[13]  Jin Yong Lee,et al.  Fluorescence turn-on sensors for HSO4-. , 2009, Chemical communications.

[14]  Huibiao Liu,et al.  Chemical sensors based on π-conjugated organic molecules and gold nanoparticles , 2009 .

[15]  Honglae Sohn,et al.  Detection of Fluorophosphonate Chemical Warfare Agents by Catalytic Hydrolysis with a Porous Silicon Interferometer , 2000 .

[16]  Juyoung Yoon,et al.  A highly selective fluorescent chemosensor for Pb2+. , 2005, Journal of the American Chemical Society.

[17]  Duong Tuan Quang,et al.  Calixarene-derived fluorescent probes. , 2007, Chemical reviews.

[18]  M. Leider.  Goodman & Gilman's The Pharmacological Basis of Therapeutics , 1985 .

[19]  T. Joo,et al.  Coumarin-derived Cu(2+)-selective fluorescence sensor: synthesis, mechanisms, and applications in living cells. , 2009, Journal of the American Chemical Society.

[20]  J.L.N. Harteveld,et al.  Studies on a surface acoustic wave (SAW) dosimeter sensor for organophosphorous nerve agents , 1997 .

[21]  A. D. Mello,et al.  PHTHALOCYANINE FLUORESCENCE AT HIGH CONCENTRATION: DIMERS OR REABSORPTION EFFECT? , 1995 .

[22]  Manoj Kumar,et al.  Terphenyl derivatives as "turn on" fluorescent sensors for mercury. , 2009, Inorganic chemistry.

[23]  T. Swager,et al.  Fluorescent detection of chemical warfare agents: functional group specific ratiometric chemosensors. , 2003, Journal of the American Chemical Society.

[24]  Ann Silver,et al.  The biology of cholinesterases , 1974 .

[25]  Herbert H Hill,et al.  Detection of a chemical warfare agent simulant in various aerosol matrixes by ion mobility time-of-flight mass spectrometry. , 2005, Analytical chemistry.

[26]  Karl J. Wallace,et al.  Detection of chemical warfare simulants by phosphorylation of a coumarin oximate. , 2006, Chemical communications.

[27]  A. R. Williams,et al.  Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer , 1983 .

[28]  Julius Rebek,et al.  Hydroxy oximes as organophosphorus nerve agent sensors. , 2009, Angewandte Chemie.

[29]  Julius Rebek,et al.  Fluorescent sensors for organophosphorus nerve agent mimics. , 2006, Journal of the American Chemical Society.

[30]  F. Becker,et al.  Samarium-induced iodine-catalyzed reduction of imines: synthesis of amine derivatives , 1999 .

[31]  Walker H. Land,et al.  Targeting Chemical and Biological Warfare Agents at the Molecular Level , 2003 .