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RESEARCH ARTICLE
Contents Vol 65(10)

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
+ Author Affiliations
- Author Affiliations

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 https://doi.org/10.1071/CH12155
Submitted: 14 March 2012  Accepted: 20 May 2012   Published: 26 June 2012

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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