Rapid and Specific Aqueous-Phase Detection of Nitroaromatic Explosives with Inherent Porphyrin Recognition Sites in Metal-Organic Frameworks

ACS Applied Materials and Interfaces

Volumn 7, Issue 22, 2015, Pages 11956-11964

  Yang, Jian ^a   Wang, Zhe ^a   Hu, Kaili ^b   Li, Yongsheng ^a   Feng, Jianfang ^b   Shi, Jianlin ^a   Gu, Jinlou ^a  

^a East China University of Science and Technology   (China)

^b SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

aqueous phase; fluorescent sensors; metal organic frameworks; porphyrin; TNT detection

Indexed keywords

AGGLOMERATION; AROMATIC COMPOUNDS; CRYSTALLINE MATERIALS; EXPLOSIVES; FLUORESCENCE; GROUND STATE; ORGANOMETALLICS; PORPHYRINS; PROBES;

2 ,4 ,6-TRINITROTOLUENE; AQUEOUS PHASE; FLUORESCENT SENSORS; METAL ORGANIC FRAMEWORK; METALORGANIC FRAMEWORKS (MOFS); NITROAROMATIC COMPOUND; NITROAROMATIC EXPLOSIVES; PUBLIC SAFETY AND SECURITIES;

EXPLOSIVES DETECTION;

EID: 84935861879     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.5b01946     Document Type: Article

References (63)

1. Che, Y.; Gross, D. E.; Huang, H.; Yang, D.; Yang, X.; Discekici, E.; Xue, Z.; Zhao, H.; Moore, J. S.; Zang, L. Diffusion-Controlled Detection of Trinitrotoluene: Interior Nanoporous Structure and Low Highest Occupied Molecular Orbital Level of Building Blocks Enhance Selectivity and Sensitivity J. Am. Chem. Soc. 2012, 134, 4978 - 4982
2. Feng, H.-T.; Wang, J.-H.; Zheng, Y.-S. CH3-π Interaction of Explosives with Cavity of a TPE Macrocycle: The Key Cause for Highly Selective Detection of TNT ACS Appl. Mater. Interfaces 2014, 6, 20067 - 20074
3. Xu, S.; Lu, H.; Li, J.; Song, X.; Wang, A.; Chen, L.; Han, S. Dummy Molecularly Imprinted Polymers-Capped CdTe Quantum Dots for the Fluorescent Sensing of 2,4,6-Trinitrotoluene ACS Appl. Mater. Interfaces 2013, 5, 8146 - 8154
4. Garcia-Reyes, J. F.; Harper, J. D.; Salazar, G. A.; Charipar, N. A.; Ouyang, Z.; Cooks, R. G. Detection of Explosives and Related Compounds by Low-Temperature Plasma Ambient Ionization Mass Spectrometry Anal. Chem. 2011, 83, 1084 - 1092
5. Yang, L. B.; Chen, G.-Y.; Wang, J.; Wang, T. T.; Li, M.-Q.; Liu, J.-H. Sunlight Induced Formation of Silver-Gold Bimetallic Nanostructures on DNA Template for Highly Active Surface Enhanced Raman Scattering Substrates and Application in TNT/Tumor Marker Detection J. Mater. Chem. 2009, 19, 6849 - 6856
6. Zang, J.; Guo, C. X.; Hu, F.; Yu, L.; Li, C. M. Electrochemical Detection of Ultratrace Nitroaromatic Explosives using Ordered Mesoporous Carbon Anal. Chim. Acta 2011, 683, 187 - 191
7. Demirel, G. B.; Daglar, B.; Bayindir, M. Extremely Fast and Highly Selective Detection of Nitroaromatic Explosive Vapors using Fluorescent Polymer Thin Films Chem. Commun. (Cambridge, U. K.) 2013, 49, 6140 - 6142
8. 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
9. Goldman, E. R.; Medintz, I. L.; Whitley, J. L.; Hayhurst, A.; Clapp, A. R.; Uyeda, H. T.; Deschamps, J. R.; Lassman, M. E.; Mattoussi, H. A Hybrid Quantum Dot-Antibody Fragment Fluorescence Resonance Energy Transfer-Based TNT Sensor J. Am. Chem. Soc. 2005, 127, 6744 - 6751
10. Freeman, R.; Finder, T.; Bahshi, L.; Gill, R.; Willner, I. Functionalized CdSe/ZnS QDs for the Detection of Nitroaromatic or RDX Explosives Adv. Mater. 2012, 24, 6416 - 6421
11. Zhang, H.; Han, Y.; Guo, Y.; Dong, C. Porphyrin Functionalized Graphene Nanosheets-Based Electrochemical Aptasensor for Label-Free ATP Detection J. Mater. Chem. 2012, 22, 23900 - 23905
12. Rahman, M.; Harmon, H. J. Absorbance Change and Static Quenching of Fluorescence of Meso-tetra(4-sulfonatophenyl)porphyrin (TPPS) by Trinitrotoluene (TNT) Spectrochim. Acta, Part A 2006, 65, 901 - 906
13. Hikal, W. M.; Harmon, H. J. Early Events in 2,4,6-Trinitrotoluene (TNT) Degradation by Porphyrins: Binding of TNT to Porphyrin by Hydrophobic and Hydrogen Bonds J. Hazard. Mater. 2008, 154, 826 - 831
14. Tao, S.; Yin, J.; Li, G. High-Performance TNT Chemosensory Materials Based on Nanocomposites with Bimodal Porous Structures J. Mater. Chem. 2008, 18, 4872 - 4878
15. Rana, A.; Panda, P. K. Fluorescent Turn-Off Based Sensing of Nitrated Explosives using Porphyrins and Their Zn(II)-Derivatives RSC Adv. 2012, 2, 12164 - 12168
16. Muthukumar, P.; John, S. A. Highly Sensitive Detection of HCl Gas using a Thin Film of Meso-tetra(4-pyridyl)porphyrin Coated Glass Slide by Optochemical Method Sens. Actuators, B 2011, 159, 238 - 244
17. Zhou, H.; Baldini, L.; Hong, J.; Wilson, A. J.; Hamilton, A. D. Pattern Recognition of Proteins Based on an Array of Functionalized Porphyrins J. Am. Chem. Soc. 2006, 128, 2421 - 2425
18. Xu, Y.; Liu, Z.; Zhang, X.; Wang, Y.; Tian, J.; Huang, Y.; Ma, Y.; Zhang, X.; Chen, Y. A Graphene Hybrid Material Covalently Functionalized with Porphyrin: Synthesis and Optical Limiting Property Adv. Mater. 2009, 21, 1275 - 1279
19. Xu, Y.; Zhao, L.; Bai, H.; Hong, W.; Li, C.; Shi, G. Chemically Converted Graphene Induced Molecular Flattening of 5,10,15,20-Tetrakis(1-methyl-4-pyridinio)porphyrin and Its Application for Optical Detection of Cadmium(II) Ions J. Am. Chem. Soc. 2009, 131, 13490 - 13497
20. 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
21. Gai, F.; Zhou, T.; Zhang, L.; Li, X.; Hou, W.; Yang, X.; Li, Y.; Zhao, X.; Xu, D.; Liu, Y.; Huo, Q. Silica Cross-Linked Nanoparticles Encapsulating Fluorescent Conjugated Dyes for Energy Transfer-Based White Light Emission and Porphyrin Sensing Nanoscale 2012, 4, 6041 - 6049
22. Yildirim, A.; Acar, H.; Erkal, T. S.; Bayindir, M.; Guler, M. O. Template-Directed Synthesis of Silica Nanotubes for Explosive Detection ACS Appl. Mater. Interfaces 2011, 3, 4159 - 4164
23. Kitagawa, S.; Kitaura, R.; Noro, S. I. Functional Porous Coordination Polymers Angew. Chem., Int. Ed. 2004, 43, 2334 - 2375
24. Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Reticular Synthesis and the Design of New Materials Nature 2003, 423, 705 - 714
25. Férey, G. Hybrid Porous Solids: Past, Present, Future Chem. Soc. Rev. 2008, 37, 191 - 214
26. Kreno, L. E.; Leong, K.; Farha, O. K.; Allendorf, M.; Van Duyne, R. P.; Hupp, J. T. Metal-Organic Framework Materials as Chemical Sensors Chem. Rev. 2012, 112, 1105 - 1125
27. Chen, B.; Xiang, S.; Qian, G. Metal-Organic Frameworks with Functional Pores for Recognition of Small Molecules Acc. Chem. Res. 2010, 43, 1115 - 1124
28. Liu, D.; Lu, K.; Poon, C.; Lin, W. Metal-Organic Frameworks as Sensory Materials and Imaging Agents Inorg. Chem. 2014, 53, 1916 - 1924
29. Yang, J.; Dai, Y.; Zhu, X.; Wang, Z.; Li, Y.; Zhuang, Q.; Shi, J.; Gu, J. Metal-Organic Frameworks with Inherent Recognition Sites for Selective Phosphate Sensing through Their Coordination-Induced Fluorescence Enhancement Effect J. Mater. Chem. A 2015, 3, 7445 - 7452
30. Hu, Z.; Deibert, B. J.; Li, J. Luminescent Metal-Organic Frameworks for Chemical Sensing and Explosive Detection Chem. Soc. Rev. 2014, 43, 5815 - 5840
31. Yang, C.-X.; Ren, H.-B.; Yan, X.-P. Fluorescent Metal-Organic Framework MIL-53(Al) for Highly Selective and Sensitive Detection of Fe3+ in Aqueous Solution Anal. Chem. 2013, 85, 7441 - 7446
32. Jiang, H.-L.; Feng, D.; Wang, K.; Gu, Z.-Y.; Wei, Z.; Chen, Y.-P.; Zhou, H.-C. An Exceptionally Stable, Porphyrinic Zr Metal-Organic Framework Exhibiting pH-Dependent Fluorescence J. Am. Chem. Soc. 2013, 135, 13934 - 13938
33. Xiao, Y.; Cui, Y.; Zheng, Q.; Xiang, S.; Qian, G.; Chen, B. A Microporous Luminescent Metal-Organic Framework for Highly Selective and Sensitive Sensing of Cu2+ in Aqueous Solution Chem. Commun. (Cambridge, U. K.) 2010, 46, 5503 - 5505
34. 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 the Fast and Reversible Detection of High Explosives Angew. Chem., Int. Ed. 2009, 48, 2334 - 2338
35. 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
36. Nagarkar, S. S.; Joarder, B.; Chaudhari, A. K.; Mukherjee, S.; Ghosh, S. K. Highly Selective Detection of Nitro Explosives by a Luminescent Metal-Organic Framework Angew. Chem. 2013, 125, 2953 - 2957
37. Asha, K. S.; Bhattacharyya, K.; Mandal, S. Discriminative Detection of Nitro Aromatic Explosives by a Luminescent Metal-Organic Framework J. Mater. Chem. C 2014, 2, 10073 - 10081
38. Ye, J.; Zhao, L.; Bogale, R. F.; Gao, Y.; Wang, X.; Qian, X.; Guo, S.; Zhao, J.; Ning, G. Highly Selective Detection of 2,4,6-Trinitrophenol and Cu2+ Ion Based on a Fluorescent Cadmium-Pamoate Metal-Organic Framework Chem.-Eur. J. 2014, 20, 1 - 10
39. Tian, D.; Li, Y.; Chen, R.-Y.; Chang, Z.; Wang, G.-Y.; Bu, X.-H. A Luminescent Metal-Organic Framework Demonstrating Ideal Detection Ability for Nitroaromatic Explosives J. Mater. Chem. A 2014, 2, 1465 - 1470
40. Wang, G.-Y.; Song, C.; Kong, D.-M.; Ruan, W.-J.; Chang, Z.; Li, Y. Two Luminescent Metal-Organic Frameworks for the Sensing of Nitroaromatic Explosives and DNA Strands J. Mater. Chem. A 2014, 2, 2213 - 2220
41. Gole, B.; Bar, A. K.; Mukherjee, P. S. Multicomponent Assembly of Fluorescent-Tag Functionalized Ligands in Metal-Organic Frameworks for Sensing Explosives Chem.-Eur. J. 2014, 20, 13321 - 13336
42. Zhang, S.-R.; Du, D.-Y.; Qin, J.-S.; Bao, S.-J.; Li, S.-L.; He, W.-W.; Lan, Y.-Q.; Shen, P.; Su, Z.-M. A Fluorescent Sensor for Highly Selective Detection of Nitroaromatic Explosives Based on a 2D, Extremely Stable, Metal-Organic Framework Chem.-Eur. J. 2014, 20, 3589 - 3594
43. Zhao, S.-N.; Song, X.-Z.; Zhu, M.; Meng, X.; Wu, L.-L.; Song, S.-Y.; Wang, C.; Zhang, H.-J. Highly Thermostable Lanthanide Metal-Organic Frameworks Exhibiting Unique Selectivity for Nitro Explosives RSC Adv. 2015, 5, 93 - 98
44. Gole, B.; Bar, A. K.; Mukherjee, P. S. Fluorescent Metal-Organic Framework for Selective Sensing of Nitroaromatic Explosives Chem. Commun. (Cambrige, U. K.) 2011, 47, 12137 - 12139
45. Xu, H.; Liu, F.; Cui, Y.; Chen, B.; Qian, G. A Luminescent Nanoscale Metal-Organic Framework for Sensing of Nitroaromatic Explosives Chem. Commun. (Cambridge, U. K.) 2011, 47, 3153 - 3155
46. Hu, Z.; Pramanik, S.; Tan, K.; Zheng, C.; Liu, W.; Zhang, X.; Chabal, Y. J.; Li, J. Selective, Sensitive, and Reversible Detection of Vapor-Phase High Explosives via Two-Dimensional Mapping: A New Strategy for MOF-Based Sensors Cryst. Growth Des. 2013, 13, 4204 - 4207
47. Dey, N.; Samanta, S. K.; Bhattacharya, S. Selective and Efficient Detection of Nitro-Aromatic Explosives in Multiple Media including Water, Micelles, Organogel, and Solid Support ACS Appl. Mater. Interfaces 2013, 5, 8394 - 8400
48. Song, X.-Z.; Song, S.-Y.; Zhao, S.-N.; Hao, Z.-M.; Zhu, M.; Meng, X.; Wu, L.-L.; Zhang, H.-J. Single-Crystal-to-Single-Crystal Transformation of a Europium(III) Metal-Organic Framework Producing a Multi-responsive Luminescent Sensor Adv. Funct. Mater. 2014, 24, 4034 - 4041
49. Nagarkar, S. S.; Desai, A. V.; Ghosh, S. K. A Fluorescent Metal-Organic Framework for Highly Selective Detection of Nitro Explosives in the Aqueous Phase Chem. Commun. (Cambridge, U. K.) 2014, 50, 8915 - 8918
50. Joarder, B.; Desai, A. V.; Samanta, P.; Mukherjee, S.; Ghosh, S. K. Selective and Sensitive Aqueous-Phase Detection of 2,4,6-Trinitrophenol (TNP) by an Amine-Functionalized Metal-Organic Framework Chem.-Eur. J. 2014, 20, 1 - 6
51. Feng, D.; Chung, W.-C.; Wei, Z.; Gu, Z.-Y.; Jiang, H.-L.; Chen, Y.-P.; Darensbourg, D. J.; Zhou, H.-C. Construction of Ultrastable Porphyrin Zr Metal-Organic Frameworks through Linker Elimination J. Am. Chem. Soc. 2013, 135, 17105 - 17110
52. Morris, W.; Volosskiy, B.; Demir, S.; Gándara, F.; McGrier, P. L.; Furukawa, H.; Cascio, D.; Stoddart, J. F.; Yaghi, O. M. Synthesis, Structure, and Metalation of Two New Highly Porous Zirconium Metal-Organic Frameworks Inorg. Chem. 2012, 51, 6443 - 6445
53. Katz, M. J.; Brown, Z. J.; Colón, Y. J.; Siu, P. W.; Scheidt, K. A.; Snurr, R. Q.; Hupp, J. T.; Farha, O. K. A Facile Synthesis of UiO-66, UiO-67 and Their Derivatives Chem. Commun. (Cambridge, U. K.) 2013, 49, 9449 - 9451
54. Lu, K.; He, C.; Lin, W. Nanoscale Metal-Organic Framework for Highly Effective Photodynamic Therapy of Resistant Head and Neck Cancer J. Am. Chem. Soc. 2014, 136, 16712 - 16715
55. Zhang, T.; Lin, W. Metal-Organic Frameworks for Artificial Photosynthesis and Photocatalysis Chem. Soc. Rev. 2014, 43, 5982 - 5993
56. Liang, X.; Li, X.; Yue, X.; Dai, Z. Conjugation of Porphyrin to Nanohybrid Cerasomes for Photodynamic Diagnosis and Therapy of Cancer Angew. Chem. 2011, 123, 11826 - 11831
57. Wang, Y.; Ni, Y. Molybdenum Disulfide Quantum Dots as a Photoluminescence Sensing Platform for 2,4,6-Trinitrophenol Detection Anal. Chem. 2014, 86, 7463 - 7470
58. Lv, Y.-Y.; Xu, W.; Lin, F.-W.; Wu, J.; Xu, Z.-K. Electrospun Nanofibers of Porphyrinated Polyimide for the Ultra-Sensitive Detection of Trace TNT Sens. Actuators, B 2013, 184, 205 - 211
59. Tu, N.; Wang, L. Surface Plasmon Resonance Enhanced Upconversion Luminescence in Aqueous Media for TNT Selective Detection Chem. Commun. (Cambridge, U. K.) 2013, 49, 6319 - 6321
60. Zou, W.-S.; Sheng, D.; Ge, X.; Qiao, J.-Q.; Lian, H.-Z. Room-Temperature Phosphorescence Chemosensor and Rayleigh Scattering Chemodosimeter Dual-Recognition Probe for 2,4,6-Trinitrotoluene Based on Manganese-Doped ZnS Quantum Dots Anal. Chem. 2011, 83, 30 - 37
61. Ingram, A. J.; Dunlap, A. G.; DiPietro, R.; Muller, G. Speciation, Luminescence, and Alkaline Fluorescence Quenching of 4-(2-Methylbutyl)aminodipicolinic Acid (H2MEBADPA) J. Phys. Chem. A 2011, 115, 7912 - 7920
62. Ma, Y.; Li, H.; Peng, S.; Wang, L. Highly Selective and Sensitive Fluorescent Paper Sensor for Nitroaromatic Explosive Detection Anal. Chem. 2012, 84, 8415 - 8421
63. Rong, M.; Lin, L.; Song, X.; Zhao, T.; Zhong, Y.-X.; Yan, J.-W.; Wang, Y.; Chen, X. A Label-Free Fluorescence Sensing Approach for Selective and Sensitive Detection of TNP in Aqueous Solution using Graphitic Carbon Nitride Nanosheets Anal. Chem. 2015, 87, 1288 - 1296