Organic Optoelectronic Materials for Trace Explosive Sensing

doi:10.7517/j.issn.1674-0475.2012.03.161

Abstract

Abstract: Detection of trace explosives is of great concern for homeland security, battlefield protection, and industrial and environmental safety control. Fluorescence quenching based sensing has proven to be one of the most promising approaches for trace explosives detection. This review is focused on examples reported by Porf. Ling Zang's group and Prof. William Trogler's group related to fluorescence quenching sensors based on one-dimensional small molecular nanomaterials, fluorescent coordination polymers (or metal-organic frameworks) and polysiloles. It is also introduced the use of organic semiconductors, such as phthalocyanine thin films and perylene diimide nanowires, to construct electronic sensors for trace explosive sensing.

Key words: explosive sensing, sensor, fluorescent compounds, trace detection

CLC Number:

ZHANG Cheng-yi, ZANG Ling. Organic Optoelectronic Materials for Trace Explosive Sensing[J]. Imaging Science and Photochemistry, 2012, 30(3): 161-174.

References

[1] Krausa M, Reznev A A. Vapour and Trace Detection of Explosives for Anti-Terrorism Purposes[M]. Boston: Kluwer Academic Publishers,2003.
[2] Marshall M,Oxley J C. Aspects of Explosives Detection[M]. Boston: Elsevier,2009.
[3] Germain M E, Knapp M J. Optical explosives detection: from color changes to fluorescence turn-on[J]. Chem. Soc. Rev., 2009, 38: 2543-2555.
[4] Toal S J, Trogler W C. Polymer sensors for nitroaromatic explosives detection[J]. J. Mater. Chem., 2006, 16: 2871-2883.
[5] Salinas Y, Martinez-Manez R, Marcos M D, Sancenon F, Costero A M, Parra M, Gil S. Optical chemosensors and reagents to detect explosives[J]. Chem. Soc. Rev., 2012, 41: 1261-1296.
[6] Yinon J. Forensic and Environmental Detection of Explosives[M]. New York: Wiley, 1999.
[7] Yinon J,Zitrin S. Modern Methods and Applications in Analysis of Explosives[M]. New York: John Wiley,1996.
[8] Moore D S. Instrumentation for trace detection of high explosives[J]. Rev. Sci. Instrum., 2004, 75:2499-2512.
[9] Sanchez J C, Trogler W C. Polymerization of a boronate-functionalized fluorophore by double transesterification: applications to fluorescence detection of hydrogen peroxide vapor[J]. J. Mater. Chem., 2008, 18:5134-5141.
[10] Xu M, Bunes B R, Zang L. Paper-based vapor detection of hydrogen peroxide: colorimetric sensing with tunable interface[J]. ACS Applied Materials & Interfaces, 2011, 3:642-647.
[11] Rhykerd C L, Hannum D W, Murray D W,Parmeter J E.Guide for the Selection of Commerial Explosives Detection Systems for Law Enforcement Applications[M]. Sandia National Laboratories, 1999.
[12] Martinez H P. Luminescent Organosilicon Polymers and Sol-Gel Synthesis of Nano-Structured Silica[M]. San Diego: University of California, 2011.
[13] Caygill J S, Davis F,Higson S P J. Current trends in explosive detection techniques[J]. Talanta, 2012, 88: 14-29.
[14] Senesac L,Thundat T G. Nanosensors for trace explosive detection[J]. Mater. Today, 2008, 11: 28-36.
[15] Thomas S W,Joly G D,Swager T M. Chemical sensors based on amplifying fluorescent conjugated polymers[J]. Chem. Rev.， 2007, 107：1339-1386.
[16] McQuade D T, Pullen A E, Swager T M.Conjugated polymer-based chemical sensors[J]. Chem. Rev., 2000, 100: 2537-2574.
[17] Yang J S, Swager T M. Porous shape persistent fluorescent polymer films:an approach to TNT sensory materials[J]. J. Am. Chem. Soc., 1998, 120: 5321-5322.
[18] Yang J S, Swager T M. Fluorescent porous polymer films as TNT chemosensors:electronic and structural effects[J]. J. Am. Chem. Soc., 1998, 120: 11864-11873.
[19] Zang L, Che Y, Moore J S. One-dimensional self-assembly of planar π-conjugated molecules: adaptable building blocks for organic nanodevices[J]. Acc. Chem. Res., 2008, 41: 1596-1608.
[20] Naddo T, Che Y, Zhang W, Balakrishnan K,Yang X,Yen M, Zhao J, Moore J S,Zang L. Detection of explosives with a fluorescent nanofibril film[J]. J. Am. Chem. Soc., 2007, 129: 6978-6979.
[21] Che Y, Yang X,Loser S, Zang L. Expedient vapor probing of organic amines using fluorescent nanofibers fabricated from an n-type organic semiconductor[J]. Nano Lett., 2008, 8:2219-2223.
[22] Zhang C,Che Y, Yang X, Bunes B R, Zang L. Organic nanofibrils based on linear carbazole trimer for explosive sensing[J]. Chem. Commun., 2010, 46: 5560-5562.
[23] Wang X, McHale R. Metal-containing polymers: building blocks for functional (nano)materials[J]. Macromol. Rapid Commun., 2010, 31: 331-350.
[24] Leong W L, Vittal J J. One-dimensional coordination polymers: complexity and diversity in structures, properties, and applications[J]. Chem. Rev., 2010, in press.
[25] Farrusseng D, Aguado S, Pinel C. Metal-organic frameworks: opportunities for catalysis[J]. Angew. Chem. Int. Ed., 2009, 48: 7502-7513.
[26] 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[J]. Angew. Chem. Int. Ed., 2009, 48： 2334-2338.
[27] Allendorf M D, Bauer C A, Bhakta R K, Houk R J T. Luminescent metal-organic frameworks[J]. Chem. Soc. Rev., 2009, 38: 1330-1352.
[28] 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]. J. Am. Chem. Soc., 2011, 133: 4153-4155.
[29] Zhang C, Che Y, Zhang Z, Yang X, Zang L. Fluorescent nanoscale zinc(Ⅱ)-carboxylate coordination polymers for explosive sensing[J]. Chem. Commun., 2011, 47:2336-2338.
[30] Zhang X, Ballem M A, Ahreén M, Suska A, Bergman P, Uvdal K. Nanoscale Ln(III)-carboxylate coordination polymers (Ln=Gd, Eu, Yb): temperature-controlled guest encapsulation and light harvesting[J]. J. Am. Chem. Soc., 2010, 132: 10391-10397.
[31] Hui J K H, MacLachlan M J. Metal-containing nanofibers via coordination chemistry[J]. Coord. Chem. Rev., 2010, 254: 2363-2390.
[32] Horcajada P, Chalati T, Serre C,Gillet B, Sebrie C,Baati T, Eubank J F,Heurtaux D, Clayette P, Kreuz C, Chang J S,Hwang Y K, Marsaud V, Bories P N,Cynober L, Gil S, Ferey G,Couvreur P, Gref R.Porous metal-organic-framework nanoscale carriers as a potential platform for drug delivery and imaging[J]. Nat. Mater., 2010, 9: 172-178.
[33] 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[J]. Chem. Mater., 2007, 19: 6459-6470.
[34] Sanchez J C, Urbas S A, Toal S J, DiPasquale A G, Rheingold A L, Trogler W C. Catalytic hydrosilylation routes to divinylbenzene bridged silole and silafluorene polymers. applications to surface imaging of explosive particulates[J]. Macromolecules, 2008, 41: 1237-1245.
[35] Toal S J, Magde D,Trogler W C. Luminescent oligo(tetraphenyl)silole nanoparticles as chemical sensors for aqueous TNT[J]. Chem. Commun., 2005, 5465-5467.
[36] Toal S J, Jones K A, Magde D, Trogler W C. Luminescent silole nanoparticles as chemoselective sensors for Cr(VI)[J]. J. Am. Chem. Soc., 2005, 127: 11661-11665.
[37] Sohn H, Sailor M J, Magde D, Trogler W C. Detection of nitroaromatic explosives based on photoluminescent polymers containing metalloles[J]. J. Am. Chem. Soc., 2003, 125: 3821-3830.
[38] 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[J]. Angew. Chem., 2001, 113: 2162-2163.
[39] Sanchez J C, Trogler W. C. Efficient blue-emitting silafluorene-fluorene-conjugated copolymers: selective turn-off/turn-on detection of explosives[J]. J. Mater. Chem., 2008, 18: 3143-3156.
[40] Trogler W.Chemical Sensing with Semiconducting Metal Phthalocyanines[M]. Mingos D M P,Day P, Dahl J P, Eds. Springer Berlin/Heidelberg, 2012. Vol. 142, pp 91-117.
[41] Bohrer F I, Colesniuc C N, Park J, Schuller I K, Kummel A C, Trogler W C. Selective detection of vapor phase hydrogen peroxide with phthalocyanine chemiresistors[J]. J. Am. Chem. Soc., 2008, 130: 3712-3713.
[42] Che Y, Yang X, Liu G, Yu C, Ji H, Zuo J, Zhao J, Zang L. Ultrathin n-type organic nanoribbons with high photoconductivity and application in optoelectronic vapor sensing of explosives[J]. J. Am. Chem. Soc., 2010, 132: 5743-5750.
[43] Zang's group webpage. http:∥www.eng.utah.edu/~lzang/.
[44] Trogler's group webpage. http:∥chem-faculty.ucsd.edu/trogler/.
[45] Swager's group. http:∥web.mit.edu/tswager/www/.
[46] FIDO explosive detector. http:∥gs.flir.com/products/icx-detection/explosives/fido/.
[47] RedX Defense. http:∥www.redxdefense.com.
[48] Vaporsens. http:∥www.vaporsens.com/.