Microwave-assisted synthesis of highly fluorescent nanoparticles of a melamine-based porous covalent organic framework for trace-level detection of nitroaromatic explosives

Journal of Hazardous Materials

Volumn 221-222, Issue , 2012, Pages 147-154

  Zhang, Wang ^a   Qiu, Ling Guang ^a   Yuan, Yu Peng ^a   Xie, An Jian ^a   Shen, Yu Hua ^a   Zhu, Jun Fa ^b  

^a ANHUI UNIVERSITY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Covalent organic frameworks; Explosive detection; Fluorescence quenching; Nanoparticles; Porous polymeric networks

Indexed keywords

2 ,4 ,6-TRINITROTOLUENE; COVALENT ORGANIC FRAMEWORKS; EXPLOSIVE DETECTION; FAST RESPONSE; FLUORESCENCE QUENCHING; FLUORESCENT NANOPARTICLES; HIERARCHICAL POROSITY; HIGH SENSITIVITY; LIGHT ELEMENTS; MICROWAVE ASSISTED SYNTHESIS; MICROWAVE-ASSISTED; NANO SCALE; NANOSCALED; NITROAROMATIC EXPLOSIVES; PICRIC ACID; POLYMERIC NETWORKS; REFLUX CONDITIONS; SENSING MATERIAL; TRACE-LEVEL DETECTION;

AROMATIC COMPOUNDS; CHEMICAL ELEMENTS; EXPLOSIVES; EXPLOSIVES DETECTION; FLUORESCENCE; NANOPARTICLES; ORGANIC SOLVENTS; POLYMERS; POROUS MATERIALS;

SYNTHESIS (CHEMICAL);

2,4,6 TRINITROPHENYLMETHYLNITRAMINE; AROMATIC NITRO COMPOUND; CARBONYL DERIVATIVE; EXPLOSIVE; MELAMINE; METAL ORGANIC FRAMEWORK; NANOPARTICLE; ORGANIC SOLVENT; PICRIC ACID; POLYMER; TRINITROTOLUENE; UNCLASSIFIED DRUG;

CHEMICAL BONDING; DETECTION METHOD; EXPLOSIVE; FLUORESCENCE; HEATING; MICROWAVE RADIATION; NANOTECHNOLOGY; ORGANIC NITROGEN COMPOUND; PARTICLE SIZE; PHENOLIC COMPOUND; POLYMER; POROSITY; POROUS MEDIUM; SOLVENT; TRINITROTOLUENE;

ABSORPTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; FLUORESCENCE; MICROWAVE RADIATION; NANOANALYSIS; PARTICLE SIZE; POROSITY; REACTION TIME; SENSITIVITY ANALYSIS; SYNTHESIS;

EXPLOSIVE AGENTS; FLUORESCENCE; LIMIT OF DETECTION; MICROSCOPY, ELECTRON, TRANSMISSION; MICROWAVES; NANOPARTICLES; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, INFRARED; TRIAZINES;

EID: 84861194121     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2012.04.025     Document Type: Article

References (68)

1. Fainberg A. Explosives detection for aviation security. Science 1992, 20:1531-1537.
2. Germain M.E., Knapp M.J. Optical explosives detection: from color changes to fluorescence turn-on. Chem. Soc. Rev. 2009, 38:2543-2555.
3. Singh S. Sensors - an effective approach for the detection of explosives. J. Hazard. Mater. 2007, 144:15-28.
4. Goodpaster J.V., McGuffin V.L. Fluorescence quenching as an indirect detection method for nitrated explosives. Anal. Chem. 2001, 73:2004-2011.
5. Olley D.A., Wren E.J., Vamvounis G., Fernee M.J., Wang X., Burn P.L., Meredith P., Shaw P.E. Explosive sensing with fluorescent dendrimers: the role of collisional quenching. Chem. Mater. 2011, 23:789-794.
6. Germain M.E., Vargo T.R., McClure B.A., Rack J.J., VanPatten P.G., Odoi M., Knapp M.J. Quenching mechanism of Zn (salicylaldimine) by nitroaromatics. Inorg. Chem. 2008, 47:6203-6211.
7. Meaney M.S., McGuffin V.L. Investigation of common fluorophores for the detection of nitrated explosives by fluorescence quenching. Anal. Chim. Acta 2008, 610:57-67.
8. Zhang K., Zhou H., Mei Q., Wang S., Guan G., Liu R., Zhang J., Zhang Z. Instant visual detection of trinitrotoluene particulates on various surfaces by ratiometric fluorescence of dual-emission quantum dots hybrid. J. Am. Chem. Soc. 2011, 133:8424-8427.
9. Salinas Y., Martínez-Máñez R., Marcos M.D., Sancenón F., Costero A.M., Parra M., Gil S. Optical chemosensors and reagents to detect explosives. Chem. Soc. Rev. 2012, 41:1261-1296.
10. Zhou Q., Swager T.M. Methodology for enhancing the sensitivity of fluorescent chemosensors: energy migration in conjugated polymers. J. Am. Chem. Soc. 1995, 117:7017-7018.
11. Yang J.-S., Swager T.M. Porous shape persistent fluorescent polymer films: an approach to TNT sensory materials. J. Am. Chem. Soc. 1998, 120:5321-5322.
12. Yang J.-S., Swager T.M. Fluorescent porous polymers films as TNT chemosensors: electronic and structural effects. J. Am. Chem. Soc. 1998, 120:11864-11873.
13. Sohn H., Sailor M.J., Magde D., Trogler W.C. Detection of nitroaromatic explosives based on photoluminescent polymers containing metalloles. J. Am. Chem. Soc. 2003, 125:3821-3830.
14. Toal S.J., Magde D., Trogler W.C. Luminescent oligo(tetraphenyl)silole nanoparticles as chemical sensors for aqueous TNT. Chem. Commun. 2005, 5465-5467.
15. Nie H., Zhao Y., Zhang M., Ma Y., Baumgarten M., Müllen K. Detection of TNT explosives with a new fluorescent conjugated polycarbazole polymer. Chem. Commun. 2011, 47:1234-1236.
16. Li J., Kendig C.E., Nesterov E.E. Chemosensory performance of molecularly imprinted fluorescent conjugated polymer materials. J. Am. Chem. Soc. 2007, 129:15911-15918.
17. Germain M.E., Knapp M.J. Discrimination of nitroaromatics and explosives mimics by a fluorescent Zn (salicylaldimine) sensor array. J. Am. Chem. Soc. 2008, 130:5422-5423.
18. Zhang C., Che Y., Yang X., Bunes B.R., Zang L. Organic nanofibrils based on linear carbazole trimer for explosive sensing. Chem. Commun. 2010, 46:5560-5562.
19. Shiraishi K., Sanji T., Tanaka M. Trace detection of explosive particulates with a phosphole oxide. ACS Appl. Mater. Interfaces 2009, 1:1379-1382.
20. Lee Y.H., Liu H., Lee J.Y., Kim S.H., Kim S.K., Sessler J.L., Kim Y., Kim S. Dipyrenylcalix[4]arene-a fluorescence-based chemosensor for trinitroaromatic explosives. Chem. Eur. J. 2010, 16:5895-5901.
21. Peng Y., Zhang A.-J., Dong M., Wang Y.-W. A colorimetric and fluorescent chemosensor for the detection of an explosive-2,4,6-trinitrophenol (TNP). Chem. Commun. 2011, 47:4505-4507.
22. 2+ nanocrystals for fluorescence detection of trace TNT explosive. Anal. Chem. 2008, 80:3458-3465.
23. 2 trigonal cages from preorganized metalloligands incorporating octahedral metal centers and fluorescent detection of nitroaromatics. Inorg. Chem. 2011, 50:1506-1512.
24. Lan A., Li K., Wu H., Olson D.H., Emge T.J., Ki W., Hong M., Li J. A luminescent microporous metal-organic framework for fast and reversible detection of high explosives. Angew. Chem. Int. Ed. 2009, 48:2334-2338.
25. Pramanik S., Zheng C., Zhang X., Emge T.J., Li J. New microporous metal-organic framework demonstrating unique selectivity for detection of high explosives and aromatic compounds. J. Am. Chem. Soc. 2011, 133:4153-4155.
26. Xu H., Liu F., Cui Y., Chen B., Qian G. A luminescent nanoscale metal-organic framework for sensing of nitroaromatic explosives. Chem. Commun. 2011, 47:3153-3155.
27. Gole B., Bar A.K., Mukherjee P.S. Fluorescent metal-organic framework for selective sensing of nitroaromatic explosives. Chem. Commun. 2011, 47:12137-12139.
28. Li R., Yuan Y.-P., Qiu L.-G., Zhang W., Zhu J-F. A rational self-sacrificing template route to metal-organic framework nanotubes and reversible vapor-phase detection of nitroaromatic explosives. Small 2012, 8:225-230.
29. Yuan Y.-P., Wang W., Qiu L.-G., Peng F.-M., Jiang X., Xie A.-J., Shen Y.-H., Tian X.-Y., Zhang L.-D. Surfactant-assisted facile synthesis of fluorescent zinc benzenedicarboxylate metal-organic framework nanorods with enhanced nitrobenzene explosives detection. Mater. Chem. Phys. 2011, 131:358-361.
30. D S.-B., Wang W., Qiu L.-G., Yuan Y.-P., Peng F.-M., Jiang X., Xie A.-J., Shen Y.-H., Zhu J.-F. Surfactant-assisted synthesis of lanthanide metal-organic framework nanorods and their fluorescence sensing of nitroaromatic explosives. Mater. Lett. 2011, 65:1385-1387.
31. Toal S.J., Trogler W.C. Polymer sensors for nitroaromatic explosives detection. J. Mater. Chem. 2006, 16:2871-2883.
32. Yildirim A., Budunoglu H., Deniz H., Guler M.O., Bayindir M. Template-free synthesis of organically modified silica mesoporous thin films for TNT sensing. ACS Appl. Mater. Interfaces 2010, 2:2892-2897.
33. Liu Y., Mills R.C., Boncella J.M., Schanze K.S. Fluorescent polyacetylene thin film sensor for nitroaromatics. Langmuir 2001, 17:7452-7455.
34. Mastalerz M. The next generation of shape-persistent zeolite analogues: covalent organic frameworks. Angew. Chem. Int. Ed. 2008, 47:445-447.
35. Maly K.E. Assembly of nanoporous organic materials from molecular building blocks. J. Mater. Chem. 2009, 19:1781-1787.
36. Uribe-Romo F.J., Hunt J.R., Furukawa H., Klöck C., O'Keeffe M., Yaghi O.M. A crystalline imine-linked 3-D porous covalent organic framework. J. Am. Chem. Soc. 2009, 131:4570-4571.
37. Furukawa H., Yaghi O.M. Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications. J. Am. Chem. Soc. 2009, 131:8875-8883.
38. Han S.S., Furukawa H., Yaghi O.M., Goddard W.A. Covalent organic frameworks as exceptional hydrogen storage materials. J. Am. Chem. Soc. 2008, 130:11580-11581.
39. Klontzas E., Tylianakis E., Froudakis G.E. Hydrogen storage in lithium-functionalized 3-D covalent-organic framework materials. J. Phys. Chem. C 2009, 113:21253-21257.
40. Wan S., Guo J., Kim J., Ihee H., Jiang D. A belt-shaped, blue luminescent, and semiconducting covalent organic framework. Angew. Chem. Int. Ed. 2008, 47:8826-8830.
41. Schwab M.G., Fassbender B., Spiess H.W., Thomas A., Feng X., Müllen K. Catalyst-free preparation of melamine-based microporous polymer networks through Schiff base chemistry. J. Am. Chem. Soc. 2009, 131:7216-7217.
42. Kappe C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 2004, 43:6250-6284.
43. Roberts B.A., Strauss C.R. Toward rapid, green, predictable microwave-assisted synthesis,. Acc. Chem. Res. 2005, 38:653-661.
44. Campbell N.L., Clowes R., Ritchie L.K., Cooper A.I. Rapid microwave synthesis and purification of porous covalent organic frameworks. Chem. Mater. 2009, 21:204-206.
45. Zhang W., Li C., Yuan Y.P., Qiu L.G., Xie A.J., Shen Y.H., Zhu J.-F. Highly energy- and time-efficient synthesis of porous triazine-based framework: microwave-enhanced ionothermal polymerization and hydrogen uptake. J. Mater. Chem. 2010, 20:6413-6415.
46. Pérez-Ramírez J., Verboekend D., Bonilla A., Abelló S. Zeolite catalysts with tunable hierarchy factor by pore-growth moderators. Adv. Funct. Mater. 2009, 19:3972-3979.
47. Lakowicz J.R. Principles of Fluorescence Spectroscopy 2006, Springer, New York, USA. 3rd ed.
48. Hong Y., Lam J.W.Y., Tang B.Z. Aggregation-induced emission. Chem. Soc. Rev. 2011, 40:5361-5388.
49. Qiu L.-G., Li Z.-Q., Wu Y., Wang W., Xu T., Jiang X. Facile synthesis of nanocrystals of a microporous metal-organic framework by an ultrasonic method and selective sensing of organoamines. Chem. Commun. 2008, 3642-3644.
50. Saxena A., Fujiki M., Rai R., Kwak G. Fluoroalkylated polysilane film as a chemosensor for explosive nitroaromatic compounds. Chem. Mater. 2005, 17:2181-2185.
51. Lu P., Lam J.W.Y., Liu J., Jim C.K.W., Yuan W., Xie N., Zhong Y., Hu Q., Wong K.S., Cheuk K.K.L., Tang B.Z. Aggregation-induced emission in a hyperbranched poly(silylenevinylene) and superamplification in its emission quenching by explosives. Macromol. Rapid Commun. 2010, 31:834-839.
52. Shanmugaraju S., Joshi S.A., Mukherjee P.S. Fluorescence and visual sensing of nitroaromatic explosives using electron rich discrete fluorophores. J. Mater. Chem. 2011, 21:9130-9138.
53. Li Z., Dong Y.Q., Lam J.W.Y., Sun J., Qin A., Häußler M., Dong Y.P., Sung H.H.Y., Williams L.D., Kwok H.S., Tang B.Z. Functionalized siloles: versatile synthesis, aggregation-induced emission, and sensory and device applications. Adv. Funct. Mater. 2009, 19:905-917.
54. Liu T., Ding L., He G., Yang Y., Wang W., Fang Y. Photochemical stabilization of terthiophene and its utilization as a new sensing element in the fabrication of monolayer-chemistry-based fluorescent sensing films. ACS Appl. Mater. Interfaces 2011, 3:1245-1253.
55. Du H., He G., Liu T., Ding L., Fang Y. Preparation of pyrene-functionalized film with a benzene ring in spacer and sensitive detection to picric acid in aqueous phase. J. Photochem. Photobiol. A: Chem. 2011, 217:356-362.
56. Xu B., Wu X., Li H., Tong H., Wang L. Selective detection of TNT and picric acid by conjugated polymer film sensors with donor-acceptor architecture. Macromolecules 2011, 44:5089-5092.
57. Sanchez J.C., DiPasquale A.G., Rheingold A.L., Trogler W.C. Synthesis, luminescence properties, and explosives sensing with 1,1-tetraphenylsilole- and 1,1-silafluorene-vinylene polymers. Chem. Mater. 2007, 19:6459-6470.
58. 3 acceptor and its fluorescent detection of nitroaromatics. Organometallics 2008, 27:316-319.
59. He G., Peng H., Liu T., Yang M., Zhang Y., Fang Y. A novel picric acid film sensor via combination of the surface enrichment effect of chitosan films and the aggregation-induced mission effect of sililes. J. Mater. Chem. 2009, 19:7347-7353.
60. Ni R., Tong R.-B., Guo C.-C., Shen G.-L., Yu R.-Q. An anthracene/porphyrin dimer fluorescence energy transfer sensing system for picric acid. Talanta 2004, 63:251-257.
61. Sohn H., Calhoun R.M., Sailor M.J., Trogler W.C. Detection of TNT and picric acid on surfaces and in seawater by using photoluminescent polysiloles. Angew. Chem. Int. Ed. 2001, 40:2104-2105.
62. Dasary S.S.R., Singh A.K., Senapati D., Yu H., Ray P.C. Gold nanoparticle based label-free SERS probe for ultrasensitive and selective detection of trinitrotoluene. J. Am. Chem. Soc. 2009, 131:13806-13812.
63. Charles P.T., Dingle B.M., Bergen S.V., Gauger P.R., Patterson C.H., Kusterbeck A.W. Enhanced biosensor performance for on-site field analysis of explosives in water using solid-phase extraction membranes. Field Anal. Chem. Technol. 2008, 42:7405-7410.
64. Rose A., Zhu Z., Madigan C.F., Swager T.M., Bulović V. Sensitivity gains in chemosensing by lasing action in organic polymers. Nature 2005, 434:876-879.
65. Apodaca D.C., Pernites R.B., Del Mundo F.R., Advincula R.C. Detection of 2,4-dinitrotoluene (DNT) as a model system for nitroaromatic compounds via molecularly imprinted short-alkyl-chain SAMs. Langmuir 2011, 27:6768-6779.
66. Content S., Trogler W.C., Sailor M.J. Detection of nitrobenzene, DNT, and TNT vapors by quenching of porous silicon photoluminescence. Chem. Eur. J. 2000, 6:2205-2213.
67. Zhang X., Qiu X., Lu R., Zhou H., Xue P., Liu X. Phenothiazine-based oligomers as novel fluorescence probes for detecting vapor-phase nitro compounds. Talanta 2010, 82:1943-1949.
68. Stringer R.C., Gangopadhyay S., Grant S.A. Detection of nitroaromatic explosives using a fluorescent-labeled imprinted polymer. Anal. Chem. 2010, 82:4015-4019.