Fluorescent porous film modified polymer optical fiber via Click chemistry: Stable dye dispersion and trace explosive detection

ACS Applied Materials and Interfaces

Volumn 7, Issue 1, 2015, Pages 241-249

  Ma, Jiajun ^a   Lv, Ling ^a   Zou, Gang ^a   Zhang, Qijin ^a  

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

Author keywords

click chemistry; explosive detection; fluorescent quenching; Poly(methyl methacrylate) optical fiber; porous film

Indexed keywords

ACRYLIC MONOMERS; AGGLOMERATION; AROMATIC COMPOUNDS; CROSSLINKING; ESTERS; EXPLOSIVES; EXPLOSIVES DETECTION; FIBERS; FLUORESCENCE; OPTICAL FIBERS; PLASTIC OPTICAL FIBERS; POLYMERIZATION; POLYMERS; PORPHYRINS; QUENCHING; SYNTHESIS (CHEMICAL);

CLICK CHEMISTRY; EXPLOSIVE DETECTION; FLUORESCENCE SELF-QUENCHING; FLUORESCENT QUENCHING; PHYSICO-CHEMICAL STABILITY; POLYHEDRAL OLIGOMERIC SILSESQUIOXANES; POROUS FILM; THIOL-ENE CLICK REACTIONS;

OPTICAL FILMS;

COLORING AGENT; EXPLOSIVE; GLASS FIBER; POLYMER;

CHEMISTRY; CLICK CHEMISTRY; FLUORESCENCE; POLYMERIZATION; POROSITY; SYNTHESIS;

CLICK CHEMISTRY; COLORING AGENTS; EXPLOSIVE AGENTS; FLUORESCENCE; OPTICAL FIBERS; POLYMERIZATION; POLYMERS; POROSITY;

EID: 84921322233     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am505950c     Document Type: Article

References (63)

1. Toal, S. J.; Trogler, W. C. Polymer Sensors for Nitroaromatic Explosives Detection J. Mater. Chem. 2006, 16, 2871-2883
2. Kartha, K. K.; Babu, S. S.; Srinivasan, S.; Ajayaghosh, A. Attogram Sensing of Trinitrotoluene with a Self-Assembled Molecular Gelator J. Am. Chem. Soc. 2012, 134, 4834-4841
3. Pushkarsky, M. B.; Dunayevskiy, I. G.; Prasanna, M.; Tsekoun, A. G.; Go, R.; Patel, C. K. N. High-Sensitivity Detection of TNT Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 19630-19634
4. Takáts, Z.; Cotte-Rodriguez, I.; Talaty, N.; Chen, H.; Cooks, R. G. Direct, Trace Level Detection of Explosives on Ambient Surfaces by Desorption Electrospray Ionization Mass Spectrometry Chem. Commun. 2005, 15, 1950-1952
5. Fayazi, M.; Ghanei-Motlagh, M.; Taher, M. A. Combination of Carbon Nanotube Reinforced Hollow Fiber Membrane Microextraction with Gas Chromatography-Mass Spectrometry for Extraction and Determination of Some Nitroaromatic Explosives in Environmental Water Anal. Methods. 2013, 5, 1474-1480
6. Piorek, B. D.; Lee, S. J.; Moskovits, M.; Meinhart, C. D. Free-Surface Microfluidics/Surface-Enhanced Raman Spectroscopy for Real-Time Trace Vapor Detection of Explosives Anal. Chem. 2012, 84, 9700-9705
7. Tam, M.; Hill, H. H. Secondary Electrospray Ionization-Ion Mobility Spectrometry for Explosive Vapor Detection Anal. Chem. 2004, 76, 2741-2747
8. Beyazkilic, P.; Yildirim, A.; Bayindir, M. Formation of Pyrene Excimers in Mesoporous Ormosil Thin Films for Visual Detection of Nitro-Explosives ACS Appl. Mater. Interfaces 2014, 6, 4997-5004
9. 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
10. 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
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. He, G.; Yan, N.; Yang, J.; Wang, H.; Ding, L.; Yin, S.; Fang, Y. Pyrene-Containing Conjugated Polymer-based Fluorescent Films for Highly Sensitive and Selective Sensing of TNT in Aqueous Medium Macromolecules 2011, 44, 4759-4766
13. 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
14. Farooq, A.; Al-Jowder, R.; Narayanaswamy, R.; Azzawi, M.; Roche, P. J.; Whitehead, D. E. Gas Detection using Quenching Fluorescence of Dye-Immobilised Silica Nanoparticles Sens. Actuators, B 2013, 183, 230-238
15. Pulido, C.; Esteban, Ó. Tapered Polymer Optical Fiber Oxygen Sensor Based on Fluorescence-Quenching of an Embedded Fluorophore Sens. Actuators, B 2013, 184, 64-69
16. Luo, Y.; Zhou, J.; Yan, Q.; Su, W.; Li, Z.; Zhang, Q.; Huang, J.; Wang, K. Optical Manipulable Polymer Optical Fiber Bragg Gratings with Azopolymer as Core Material Appl. Phys. Lett. 2007, 91, 071110
17. Mizuno, Y.; Hayashi, N.; Tanaka, H.; Nakamura, K.; Todoroki, S.-i. Observation of Polymer Optical Fiber Fuse Appl. Phys. Lett. 2014, 104, 043302
18. 3 Phen-doped Polymer Optical Fiber Opt. Lett. 2004, 29, 477-479
19. Luo, Y.; Zhang, Q.; Liu, H.; Peng, G.-D. Gratings Fabrication in Benzildimethylketal Doped Photosensitive Polymer Optical Fibers using 355 nm Nanosecond Pulsed Laser Opt. Lett. 2010, 35, 751-753
20. Hu, Z.; Miao, B.; Wang, T.; Fu, Q.; Zhang, D.; Ming, H.; Zhang, Q. Disordered Microstructure Polymer Optical Fiber for Stabilized Coherent Random Fiber Laser Opt. Lett. 2013, 38, 4644-4647
21. Ho, M.-L.; Wang, J.-C.; Wang, T.-Y.; Lin, C.-Y.; Zhu, J. F.; Chen, Y.-A.; Chen, T.-C. The Construction of Glucose Biosensor Based on Crystalline Iridium (III)-Containing Coordination Polymers with Fiber-Optic Detection Sens. Actuators, B 2014, 190, 479-485
22. MacCraith, B. D.; McDonagh, C. M.; O'Keeffe, G.; Keyes, E. T.; Vos, J. G.; O'Kelly, B.; McGilp, J. F. Fibre Optic Oxygen Sensor Based on Fluorescence Quenching of Evanescent-Wave Excited Ruthenium Complexes in Sol-Gel Derived Porous Coatings Analyst 1993, 118, 385-388
23. Tang, X.; Provenzano, J.; Xu, Z.; Dong, J.; Duan, H.; Xiao, H. Acidic ZSM-5 Zeolite-Coated Long Period Fiber Gating for Optical Sensing of Ammonia J. Mater. Chem. 2011, 21, 181-186
24. Zhao, Q.; Yin, M.; Zhang, A. P.; Prescher, S.; Antonietti, M.; Yuan, J. Hierarchically Structured Nanoporous Poly (Ionic Liquid) Membranes: Facile Preparation and Application in Fiber-Optic pH Sensing J. Am. Chem. Soc. 2013, 135, 5549-5552
25. Zhang, Y.; Xue, L.; Wang, T.; Yang, L.; Zhu, B.; Zhang, Q. High Performance Temperature Sensing of Single Mode-Multimode-Single Mode Fiber with Thermo-Optic Polymer as Cladding Of Multimode Fiber Segment IEEE Sens. J. 2014, 14, 1143-1147
26. 2 Dissolved in Water Appl. Phys. B: Lasers Opt. 2008, 90, 355-360
27. Van Bergen, S. K.; Bakaltcheva, I. B.; Lundgren, J. S.; Shriver-Lake, L. C. On-Site Detection of Explosives in Groundwater with a Fiber Optic Biosensor Environ. Sci. Technol. 2000, 34, 704-708
28. Cennamo, N.; D'Agostino, G.; Galatus, R.; Bibbo, L.; Pesavento, M.; Zeni, L. Sensors Based on Surface Plasmon Resonance in a Plastic Optical Fiber for The Detection of Trinitrotoluene Sens. Actuators, B 2013, 188, 221-226
29. El Hamzaoui, H.; Bigot, L.; Bouwmans, G.; Razdobreev, I.; Bouazaoui, M.; Capoen, B. From Molecular Precursors in Solution to Microstructured Optical Fiber: A Sol-Gel Polymeric Route Opt. Mater. Express. 2011, 1, 234-242
30. Chu, C.-S.; Lo, Y.-L. Optical Fiber Dissolved Oxygen Sensor Based on Pt (II) Complex and Core-Shell Silica Nanoparticles Incorporated with Sol-Gel Matrix Sens. Actuators, B 2010, 151, 83-89
31. Yeh, T.-S.; Chu, C.-S.; Lo, Y.-L. Highly Sensitive Optical Fiber Oxygen Sensor using Pt (II) Complex Embedded in Sol-Gel Matrices Sens. Actuators, B 2006, 119, 701-707
32. Fierke, M. A.; Olson, E. J.; Bühlmann, P.; Stein, A. Receptor-Based Detection of 2,4-Dinitrotoluene using Modified Three-Dimensionally Ordered Macroporous Carbon Electrodes ACS Appl. Mater. Interfaces 2012, 4, 4731-4739
33. 2 Monolayer Ordered Porous Films with Size-Tunable Surface Pores for Direct Application in Resistive-Type Gas Sensor ACS Appl. Mater. Interfaces 2014, 6, 1251-1257
34. Lee, D.; Kim, S.; Jeon, S.; Thundat, T. Direct Detection and Speciation of Trace Explosives using a Nanoporous Multi-Functional Microcantilever Anal. Chem. 2014, 86, 5077-5082
35. Vu, A.; Phillips, J.; Bühlmann, P.; Stein, A. Quenching Performance of Surfactant-Containing and Surfactant-Free Fluorophore-Doped Mesoporous Silica Films for Nitroaromatic Compound Detection Chem. Mater. 2013, 25, 711-722
36. Alves, F.; Scholder, P.; Nischang, I. Conceptual Design of Large Surface Area Porous Polymeric Hybrid Media Based on Polyhedral Oligomeric Silsesquioxane Precursors: Preparation, Tailoring of Porous Properties, and Internal Surface Functionalization ACS Appl. Mater. Interfaces 2013, 5, 2517-2526
37. Nischang, I.; Brüggemann, O.; Teasdale, I. Facile, Single-Step Preparation of Versatile, High-Surface-Area, Hierarchically Structured Hybrid Materials Angew. Chem., Int. Ed. 2011, 50, 4592-4596
38. Kiba, S.; Okawauchi, Y.; Yanagihara, T.; Murakami, M.; Shimizu, T.; Yamauchi, Y. Mesoporous Silica/Polymer Composites utilizing Intelligent Caps onto Mesopore Walls toward Practical Low-Dielectric Materials Chem. - Asian J. 2009, 4, 1798-1801
39. Milliman, H. W.; Boris, D.; Schiraldi, D. A. Experimental Determination of Hansen Solubility Parameters for Select POSS and Polymer Compounds as a Guide to POSS-Polymer Interaction Potentials Macromolecules 2012, 45, 1931-1936
40. Tuteja, A.; Choi, W.; Ma, M.; Mabry, J. M.; Mazzella, S. A.; Rutledge, G. C.; McKinley, G. H.; Cohen, R. E. Designing Superoleophobic Surfaces Science 2007, 318, 1618-1622
41. Chatterjee, S.; Ramakrishnan, S. Defect-Free Hyperbranched Polydithioacetal via Melt Polymerization ACS Macro Lett. 2012, 1, 593-598
42. Yang, T.; Long, H.; Malkoch, M.; Kristofer, E.; Berglund, L.; Hult, A. Characterization of Well-Defined Poly (Ethylene Glycol) Hydrogels Prepared by Thiol-Ene Chemistry J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 4044-4054
43. Jeong, E. Y.; Burri, A.; Lee, S. Y.; Park, S. E. Synthesis and Catalytic Behavior of Tetrakis (4-Carboxyphenyl) Porphyrin-Periodic Mesoporous Organosilica J. Mater. Chem. 2010, 20, 10869-10875
44. Gaspar, B.; Carreira, E. M. Mild Cobalt-Catalyzed Hydrocyanation of Olefins with Tosyl Cyanide Angew. Chem., Int. Ed. 2007, 46, 4519-4522
45. Khijwania, S. K.; Srinivasan, K. L.; Singh, J. P. An Evanescent-Wave Optical Fiber Relative Humidity Sensor with Enhanced Sensitivity Sens. Actuators, B 2005, 104, 217-222
46. 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
47. 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
48. 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
49. Sparks, B. J.; Hoff, E. F.; Xiong, L.; Goetz, J. T.; Patton, D. L. Superhydrophobic Hybrid Inorganic-Organic Thiol-ene Surfaces Fabricated via Spray-Deposition and Photopolymerization ACS Appl. Mater. Interfaces 2013, 5, 1811-1817
50. Northrop, B. H.; Coffey, R. N. Thiol-Ene Click Chemistry: Computational and Kinetic Analysis of the Influence of Alkene Functionality J. Am. Chem. Soc. 2012, 134, 13804-13817
51. Leung, A.; Shankar, P. M.; Mutharasan, R. A Review of Fiber-Optic Biosensors Sens. Actuators, B 2007, 125, 688-703
52. Sai, V.; Kundu, T.; Mukherji, S. Novel U-Bent Fiber Optic Probe for Localized Surface Plasmon Resonance Based Biosensor Biosens. Bioelectron. 2009, 24, 2804-2809
53. Gupta, B.; Dodeja, H.; Tomar, A. Fibre-Optic Evanescent Field Absorption Sensor Based on a U-Shaped Probe Opt. Quantum Electron. 1996, 28, 1629-1639
54. Ton, X. A.; Tse Sum Bui, B.; Resmini, M.; Bonomi, P.; Dika, I.; Soppera, O.; Haupt, K. A Versatile Fiber-Optic Fluorescence Sensor Based on Molecularly Imprinted Microstructures Polymerized in situ Angew. Chem., Int. Ed. 2013, 52, 8317-8321
55. Xue, Y.; Wang, H.; Yu, D.; Feng, L.; Dai, L.; Wang, X.; Lin, T. Superhydrophobic Electrospun POSS-PMMA Copolymer Fibres with Highly Ordered Nanofibrillar and Surface Structures Chem. Commun. 2009, 42, 6418-6420
56. Monticelli, O.; Fina, A.; Cozza, E. S.; Prato, M.; Bruzzo, V. POSS Vapor Phase Grafting: A Novel Method to Modify Polymer Films J. Mater. Chem. 2011, 21, 18049-18054
57. Yan, Z.; Xu, H.; Guang, S.; Zhao, X.; Fan, W.; Liu, X. Y. A Convenient Organic-Inorganic Hybrid Approach Toward Highly Stable Squaraine Dyes with Reduced H-Aggregation Adv. Funct. Mater. 2012, 22, 345-352
58. Chen, Q.; Xu, R.; Zhang, J.; Yu, D. Polyhedral Oligomeric Silsesquioxane (POSS) Nanoscale Reinforcement of Thermosetting Resin from Benzoxazine and Bisoxazoline Macromol. Rapid Commun. 2005, 26, 1878-1882
59. Quiroz-Segoviano, R. I.; Serratos, I. N.; Rojas-González, F.; Tello-Solís, S. R.; Sosa-Fonseca, R.; Medina-Juárez, O.; Menchaca-Campos, C.; García-Sánchez, M. A. On Tuning The Fluorescence Emission of Porphyrin Free Bases Bonded to the Pore Walls of Organo-Modified Silica Molecules 2014, 19, 2261-2285
60. Wirnsberger, G.; Stucky, G. D. Microring Lasing from Dye-Doped Silica/Block Copolymer Nanocomposites Chem. Mater. 2000, 12, 2525-2527
61. 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
62. Tao, S.; Li, G. Porphyrin-Doped Mesoporous Silica Films for Rapid TNT Detection Colloid Polym. Sci. 2007, 285, 721-728
63. 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