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N-2-Propenyl-(5-dimethylamino)-1-naphthalene Sulfonamide, a Novel Fluorescent Monomer for the Molecularly Imprinted Polymer-Based Detection of 2,4-Dinitrotoluene in the Gas Phase
Nicholas W.
Turner A B,
Clovia I.
Holdsworth A,
Adam
McCluskey C and
Michael C.
Bowyer A D
A
Centre for Organic Electronics, Chemistry Building, School of Environmental and Life Sciences, University of Newcastle, Callaghan, NSW 2308, Australia.
B
Current address: Department of Chemistry and Analytical Sciences, Open University, Walton Hall, Milton Keynes, MK7 6AA, United Kingdom.
C
Centre for Chemical Biology, Chemistry Building, School of Environmental and Life Sciences, University of Newcastle, Callaghan, NSW 2308, Australia.
D
Corresponding author. Email: Michael.Bowyer@newcastle.edu.au
Australian Journal of Chemistry
65(10)
1405-1412 http://dx.doi.org/10.1071/CH12155
Submitted: 14 March 2012 Accepted: 20 May 2012 Published:
26
June
2012
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Abstract
Fluorescent molecularly imprinted polymers (MIP) specific for 2,4-dinitrotoluene (DNT) have been synthesised using a novel monomer N-2-propenyl-(5-dimethylamino)-1-naphthalene sulfonamide. Three formats of the polymer were produced: a traditional bulk monolith ground into particles, a flexible, but highly cross-linked plasticiser-modified free standing membrane, and a hybrid material consisting of particles embedded in a poly(acrylonitrile) phase inversed film. Within all materials, a clearly defined imprinting effect was observed upon exposure to DNT vapour at room temperature. In all cases, preferential rebinding of DNT to the molecularly imprinted materials (3–5 times) over their non-imprinted (NIP) equivalents was evident within <10 min of contact with the DNT vapour stream. Fluorographic images of the fluorescent polymers showed the DNT binding-induced quenching to be significantly higher in the MIP material than in the non-imprinted control polymer. 
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References
[1]
R. G. Ewing, D. A. Atkinson, G. A. Eiceman, G. J. Ewing, Talanta 2001, 54, 515.
| CrossRef | CAS | 
[2]
FIDO Technical Overview Pamphlet. Available at: http://gs.flir.com/uploads/file/products/brochures/fido%20technical%20overview.pdf (accessed 11 November 2011).
[3]
S. Toal, W. C. Trogler, J. Mater. Chem. 2006, 16, 2871.
| CrossRef | CAS |
[4]
A. McCluskey, C. I. Holdsworth, M. C. Bowyer, Org. Biomol. Chem. 2007, 5, 3233.
| CrossRef | CAS |
[5]
C. Alexander, H. S. Andersson, L. I. Andersson, R. J. Ansell, N. Kirsch, I. A. Nicholls, J. O’Mahony, M. Whitcombe, J. Mol. Recognit. 2006, 19, 106.
| CrossRef | CAS |
[6]
N. W. Turner, C. W. Jeans, K. R. Brain, C. J. Allender, V. H. Hlady, D. W. Britt, Biotechnol. Prog. 2006, 22, 1474.
| CAS |
[7]
D. S. Moore, Rev. Sci. Instrum. 2004, 75, 2499.
| CrossRef | CAS |
[8]
C. Xie, B. Liu, Z. Wang, D. Gao, G. Guan, Z. Zhang, Anal. Chem. 2008, 80, 437.
| CrossRef | CAS |
[9]
C. Xie, Z. Zhang, D. Wang, G. Guan, D. Gao, J. Liu, Anal. Chem. 2006, 78, 8339.
| CrossRef | CAS |
[10]
D. Gao, Z. Zhang, M. Wu, C. Xie, G. Guan, D. Wang, J. Am. Chem. Soc. 2007, 129, 7859.
| CrossRef | CAS |
[11]
M. Riskin, R. Tel-Vered, T. Bourenko, E. Granot, I. Willner, J. Am. Chem. Soc. 2008, 130, 9726.
| CrossRef | CAS |
[12]
N. R. Walker, M. J. Linman, M. M. Timmers, S. L. Dean, C. M. Burkett, J. A. Llloyd, J. D. Keelor, B. M. Baughman, P. L. Edminston, Anal. Chim. Acta 2007, 593, 82.
| CrossRef | CAS |
[13]
G. Bunte, J. Hurttlen, H. Pontius, K. Hartlieb, H. Krause, Anal. Chim. Acta 2007, 591, 49.
| CrossRef | CAS |
[14]
M.-J. Ju, D.-H. Yang, N. Takahara, K. Hayashi, K. Toko, S.-W. Lee, T. Kunitake, Chem. Commun. (Camb.) 2007, 2630.
| CrossRef | CAS |
[15]
P. Turkewitsch, B. Wandelt, G. D. Darling, W. S. Powell, Anal. Chem. 1998, 70, 2025.
| CrossRef | CAS |
[16]
Y. Liao, W. Wang, B. Wang, Bioorg. Chem. 1999, 27, 463.
| CrossRef | CAS |
[17]
T. Takeuchi, T. Mukawa, J. Matsui, M. Higashi, K. D. Shimuzu, Anal. Chem. 2001, 73, 3869.
| CrossRef | CAS |
[18]
W. Wang, S. Gao, B. Wang, Org. Lett. 1999, 1, 1209.
| CrossRef | CAS |
[19]
S. Subrahmanyam, S. A. Piletsky, E. V. Piletska, B. N. Chen, R. Day, A. P. F. Turner, Adv. Mater. 2000, 12, 722.
| CrossRef | CAS |
[20]
S. McNiven, I. Karube, in Molecularly Imprinted Polymers: Man-Made Mimics of Antibodies and their Applications in Analytical Chemistry, (Ed. B. Sellergren) 2001, Volume 23, p. 467 (Elsevier: Amsterdam).
[21]
D. L. Rathbone, A. Bains, Biosens. Bioelectron. 2005, 20, 1438.
| CrossRef | CAS |
[22]
I. Chianella, M. Lotierzo, S. A. Piletsky, I. E. Tothill, B. Chen, K. Karim, A. P. F. Turner, Anal. Chem. 2002, 74, 1288.
| CrossRef | CAS |
[23]
N. W. Turner, M. Whitcombe, M. Malecha, K. Karim, C. Baggiani, S. A. Piletsky, Biosens. Bioelectron. 2004, 20, 1060.
| CrossRef | CAS |
[24]
Molecular Imprinting of Polymers, (Eds S. A. Piletsky, A.Turner) 2006 (Landes Bioscience: Austin, TX).
[25]
D. L. Rathbone, G. Yi, Anal. Chim. Acta 2001, 435, 129.
| CrossRef | CAS |
[26]
T. A. Sergeyeva, O. O. Brovko, E. V. Piletska, S. A. Piletsky, L. A. Goncharova, L. V. Karabanova, L. M. Sergeyeva, A. V. El’skaya, Anal. Chim. Acta 2007, 582, 311.
| CrossRef | CAS |
[27]
T. A. Sergeyeva, S. A. Piletsky, A. A. Brovko, E. A. Slinchenko, L. M. Sergeyeva, A. V. El’skaya, Anal. Chim. Acta 1999, 392, 105.
| CrossRef | CAS |
[28]
T. A. Sergeyeva, S. A. Piletsky, A. A. Brovko, E. A. Slinchenko, L. M. Sergeyeva, T. L. Panasyuk, A. V. El’skaya, Analyst (Lond.) 1999, 124, 331.
| CrossRef | CAS |
[29]
B. Sellergren, Trends Analyt. Chem. 1999, 18, 164.
| CrossRef | CAS |
[30]
B. Sellergren, in Molecularly Imprinted Polymers: Man-Made Mimics of Antibodies and their Applications in Analytical Chemistry, (Ed. B. Sellergren) 2001, Volume 23, p. 113 (Elsevier: Amsterdam).
[31]
X. Kan, Q. Zhao, Z. Zhang, Z. Wang, J.-J. Zhu, Talanta 2008, 75, 22.
| CrossRef | CAS |
[32]
Q. Yao, Y. Zhou, J. Inorg. Organomet. P. 2009, 19, 215.
| CrossRef | CAS |
[33]
Q. Yao, Y. Zhou, Y. Sun, X. Ye, J. Inorg. Organomet. P. 2008, 18, 477.
| CrossRef | CAS |
[34]
K. Takeda, T. Kobayashi, J. Membr. Sci. 2006, 275, 61.
| CrossRef | CAS |
[35]
N. W. Turner, C. Brisbane, N. Holmes, A. B. McGeachie, C. I. Holdsworth, M. C. Bowyer, A. McCluskey, Effect of Template on Formation of Phase-Inversed Molecularly Imprinted Films. Contributed paper presented at MIP2008 – the 5th International Workshop on Molecular Imprinting, Kobe University, 7–11 September 2008.
[36]
M. Bompart, L. A. Gheber, Y. De Wilde, K. Haupt, Biosens. Bioelectron. 2009, 25, 568.
| CrossRef | CAS |
[37]
K. Hunter, in Polyamine Protocols, (Ed. D. M. L. Morgan) 1998, Volume 79, p. 119 (Humana Press: New York, NY).
[38]
P. Ceroni, I. Laghi, M. Maestri, V. Blazani, S. Gestermann, M. Gorka, F. Vogtle, New J. Chem. 2002, 26, 66.
| CrossRef | CAS |
[39]
J. H. Rothman, W. C. Still, Bioorg. Med. Chem. Lett. 1999, 9, 509.
| CrossRef | CAS |
[40]
T. K. Wang, M. S. Fuh, J. Chromatogr. B 1996, 686, 285.
| CrossRef | CAS |
[41]
S. Caddick, J. D. Wilden, D. B. Judd, J. Am. Chem. Soc. 2004, 126, 1024.
| CrossRef | CAS |
[42]
S. A. Piletsky, K. Karim, I. E. Piletska, C. J. Day, K. W. Freebairn, C. H. Legge, A. P. F. Turner, Analyst 2001, 126, 1826.
| CrossRef | CAS |
[43]
V. L. Nixon, M. Levasseur, M. McDougall, K. T. Jones, Curr. Biol. 2002, 12, 746.
| CrossRef | CAS |
[44]
A. Reis, M. Levasseur, H.-Y. Chang, D. J. Elliot, K. T. Jones, EMBO Rep. 2006, 7, 1040.
| CrossRef | CAS |
|
|
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