A Type of Conjugated Fuse Heterocyclic Schiff Base Colorimetric and Fluorescent Chemosensors for Selective Detection of Picric acid (PA) | [Journal of Chemical Society of Pakistan • 2024]

Author(s):

1. Tianzhu Shi: Department of Brewing Engineer ing, Moutai Institute, Renhuai 564500, China; Oil & Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500, China.

2. Zhengfeng Xie: Oil & Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500, China.

3. Fuyong Wu: Department of Brewing Engineer ing, Moutai Institute, Renhuai 564500, China

4. Yulong Feng: Department of Brewing Engineer ing, Moutai Institute, Renhuai 564500, China

5. Tao Peng: Department of Brewing Engineer ing, Moutai Institute, Renhuai 564500, China

6. Dezhi Yuan: Department of Brewing Engineer ing, Moutai Institute, Renhuai 564500, China

Abstract:

Summary: A series of Schiff base chemosensors (M1, M2 and M3) were designed and synthesized based on conjugated fuse heterocyclic aldehyde thiosemicarbazone. Optical properties of fluorescent probes M1, M2, and M3 toward various nitro explosives 2,4-dinitrotoluene (DNT), o-nitrophenol (ONP), p-nitrophenol (PNP), phenol (PhOH) and nitromethane (NM) were investigated, M1, M2, and M3 could selectively recognize PA with an obvious color change and fluorescence quenching, even in the presence of other coexistence nitro explosives. The detection limit of M1, M2, and M3 were 1.18×10-7 M, 1.13×10-7 M, 1.09×10-7 M, respectively.

Page(s): 377-385

DOI: 10.52568/001506/JCSP

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 46, Issue: 4, Year: 2024

Keywords:

Schiff bases , Picric acid PA , Fluorescence probe , Thiosemicarbazone

References:

[1] Germain M. E.,Knapp M. J. .2009 .Optical explosives detection: from color changes to fluorescence turn-on. Chem. Soc. Rev., 38(2543) : .

[2] Ma Y.,Wang S.,Wang L. .2015 .Nanomaterials for luminescence detection of nitroaromatic explosives. TrAC Trends in Analytical Chemistry, 65(13) : .

[3] Chowdhury A.,Mukherjee P.S. .2015 .Electron-Rich Triphenylamine-Based Sensors for Picric Acid Detection. J. Org. Chem, 80(4064) : .

[4] Sun X.,Shaw G. .2015 .Fundamental study of electrospun pyrene-polyethersulfone nanofibers using mixed solvents for sensitive and selective explosives detection in aqueous solution. ACS Appl. Mater. Interfaces, 7(13189) : .

[5] Gogoi B.,Sarma N. Sen .2015 .Curcumin-Cysteine and Curcumin-Tryptophan Conjugate as Fluorescence Turn On Sensors for Picric Acid in Aqueous Media. ACS Appl. Mater. Interfaces, 7 : 11195.

[6] Mukherjee S.,Desai A.V.,Inamdar A.I .2015 .by a π-Stacked Organic Crystalline Solid in Water. Cryst. Growth Des, 15(3493) : 6-Trinitrophenol.

[7] Bhalla V.,Kaur S.,Vij V.,M. V. .2013 .Kumar, MercuryModulated Supramolecular Assembly of a Hexaphenylbenzene Derivative for Selective Detection of Picric Acid. , 52(4860) : .

[8] Wyman J.,Serve M.,Hobson D.,Part A .1992 .Safety data sheet for picric acid. resource of National Institute of Health. J. Toxicol. Environ, 37(313) : .

[9] Kumar M.,Reja S.I,Bhalla V. .2012 .A charge transfer amplified fluorescent Hg2+ complex for detection of picric acid and construction of logic functions. , 14(6084) : .

[10] J. Shen J.,Zhang Y.,Zuo Y. .2009 .-trinitrophenol by Rhodococcus sp. isolated from a picric acid-contaminated soil. J. Hazard. Mater., 163(1199) : .

[11] Huynh T.P.,Sosnowska M.,Sobczak J.W. .2013 .Simultaneous chronoamperometry and piezoelectric microgravimetry determination of nitroaromatic explosives using molecularly imprinted thiophene polymers. Anal. Chem, 85(8361) : .

[12] J.M. Sylvia J.A.,Janni J.,Klein J. .2000 .-dinitrotoluene impurity vapor as a marker to locate landmines. Anal. Chem, 72(5834) : .

[13] Dasary S.S.,Singh A.K.,Senapati D. .2009 .Gold nanoparticle based label-free SERS probe for ultrasensitive and selective detection of trinitrotoluene. J. Am. Chem. Soc., 131(13806) : .

[14] López-López C.,García-Ruiz C. .2014 .Infrared and Raman spectroscopy techniques applied to identification of explosives. TrAC Trends in Anal. Chem, 54(36) : .

[15] Steinfeld J.I.,Wormhoudt J. .1998 .Explosives detection: a challenge for physical chemistry. Annu. Rev. Phys. Chem, 49(203) : .

[16] Talaty N.,Mulligan C.C.,Justes D.R. .2008 .Fabric analysis by ambient mass spectrometry for explosives and drugs. Analyst, 133(1532) : .

[17] Barron .2014 .Ion chromatographymass spectrometry: A review of recent technologies and applications in forensic and environmental explosives analysis. Anal. Chim. Acta, 806(27) : .

[18] M. Tam H.H.,Hill H.H. .2004 .Secondary electrospray ionization-ion mobility spectrometry for explosive vapor detection. Anal. Chem, 76(2741) : .

[19] M. Najarro M.E.D.,Morris M.E.,Staymates M.E. .2012 .Optimized thermal desorption for improved sensitivity in trace explosives detection by ion mobility spectrometry. Analyst, 137(2614) : .

[20] K.M. Roscioli E.,Davis W.F.,Siems W.F. .2011 .Modular ion mobility spectrometer for explosives detection using corona ionization. Anal. Chem, 83(5965) : .

[21] Forzani E.S.,Lu D,Leright M.J .2009 .A hybrid electrochemical−colorimetric sensing platform for detection of explosives. J. Am. Chem. Soc., 131(1390) : .

[22] Yang T.M.,Swager T.M. .1998 .Fluorescent porous polymer films as TNT chemosensors: electronic and structural effects. J. Am. Chem. Soc., 120(11864) : .

[23] Zhang R.,Sun C.,Lu Y.,Graphene NanoribbonSupported PtPd Concave Y. .2015 .Nanocubes for Electrochemical Detection of TNT with High Sensitivity and Selectivity. Anal. Chem, 87(12262) : .

[24] J. Xiong J.,Li G.,Mo G. .2014 .Benzimidazole derivatives: selective fluorescent chemosensors for the picogram detection of picric acid. J. Org. Chem, 79(11619) : .

[25] M. Rong L.,Lin X.,Song X. .2014 .A Label-Free Fluorescence Sensing Approach for Selective and Sensitive Detection of 2, 4, 6-Trinitrophenol (TNP) in Aqueous Solution Using Graphitic Carbon Nitride Nanosheets. Anal. Chem, 87(1288) : .

[26] Roy B.,Bar A.K.,Gole B. .2013 .Fluorescent trisimidazolium sensors for picric acid explosive. J. Org. Chem, 78(1306) : .

[27] A.H. Malik S.,Hussain A.,Kalita A. .2015 .Conjugated polymer nanoparticles for the amplified detection of nitro-explosive picric acid on multiple platforms. ACS Appl. Mater. Interfaces, 7(26968) : .

[28] P.G. Del Rosso M.J.,Romagnoli M.F.,Almassio M.F. .2014 .Diphenylanthrylene and diphenylfluorenebased segmented conjugated polymer films as fluorescent chemosensors for nitroaromatics in aqueous solution. Sensors and Actuators B: Chemical, 203(612) : .

[29] Toal S.J.,Trogler W.C. .2006 .Polymer sensors for nitroaromatic explosives detection. J. Mater. Chem, 16(2871) : .

[30] Lin M. Rong S.,Lu S. .2015 .A facile synthesis of highly luminescent nitrogen-doped graphene quantum dots for the detection of 2, 4, 6- trinitrophenol in aqueous solution. Nanoscale, 7 : .

[31] Lu H.,Li J. .2013 .Dummy molecularly imprinted polymers-capped CdTe quantum dots for the fluorescent sensing of 2,. ACS Appl. Mater. Interfaces, 5(8146) : 6-Trinitrotoluene.

[32] Hu Z.,Li B.J. Deibert J. .2014 .Luminescent metalorganic frameworks for chemical sensing and explosive detection. Chem. Soc. Rev., 43(5815) : .

[33] Nagarkar S.S.,Desai A.V.,Ghosh S.K. .2014 .A fluorescent metal-organic framework for highly selective detection of nitro explosives in the aqueous phase. Chem, 50(8915) : .

[34] Sanda S.,Parshamoni S.,Biswas S. .2015 .Highly selective detection of palladium and picric acid by a luminescent MOF: a dual functional fluorescent sensor. Chem, 51(6576) : .

[35] Dey N.,Samanta S.K.,Bhattacharya S. .2013 .Selective and efficient detection of nitro-aromatic explosives in multiple media including water, micelles, organogel, and solid support. ACS Appl. Mater. Interfaces, 5(8394) : .

[36] J.M. Delente D.,Umadevi S. .2020 .Aggregation induced emission (AIE) active 4- amino-1,8-naphthalimide-Troger's base for the selective sensing of chemical explosives in competitive aqueous media. Chem, 56(2562) : .

[37] M.E.H. Fassbender Y.,Huang Y.,Hu Y. .2018 .Selective biosorption of thorium (IV) from aqueous solutions by ginkgo leaf. Plos One, 13 : .

[38] Chen Y.,Shi W.,Hui Y. .2015 .A new highly selective fluorescent turn-on chemosensor for cyanide anion. Talanta, 137(38) : .

[39] Lin H.,Shi W.,Tian Y. .2015 .-carbonyl) thiosemicarbazide. -[1, 157(280) : triazole.

[40] Hong D.,Lee R.,Choi R.G. .2010 .Self-organized spiral columns in laterally grafted rods. Chem, 46(4896) : .

[41] Guo Z.,Lei T.,Jin Z. .2013 .T‑Shaped DonorAcceptor Molecules for Low-Loss Red-Emission Optical Waveguide. , 15(3530) : .

[42] Thomsen V.,Schatzlein D.,Mercuro D. .2003 .Limits of detection in spectroscopy. Spectroscopy, 18(112) : .

[43] Xu X.,Wu H.,Li H. .2011 .Selective detection of TNT and picric acid by conjugated polymer film sensors with donor-acceptor architecture. Macromolecules, 44(5089) : .

[44] M. Bai S.,Huang S.,Xu S. .2015 .Fluorescent Nanosensors via Photoinduced Polymerization of Hydrophobic Inorganic Quantum Dots for the Sensitive and Selective Detection of Nitroaromatics. Anal. Chem, 87(2383) : .

Citations

Downloads

Views