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Reversible adsorption and storage of secondary explosives from water using a Tröger’s base-functionalised Polymer

Abstract

A Tröger’s base-functionalised covalent organic polymer (TB-COP) was synthesized and used as a molecular fil-ter/adsorbent for the efficient removal of picric acid (PA) from water through the use of weak and reversible supramolecular interactions such as hydrogen bonding and π−π interactions. The TB-COP was readily synthesised in quantitative yield using a one-pot metal-free polymerization reaction strategy between a semi-flexible aromatic triamine [L; benzene-1,3-5-tricarboxylic acid-tris-(4-amino-phenyl-amide)] and di-methoxymethane. The molecular structure, physicochemical and morphological characteristics of TB-COP were analyzed by using various spectroscopic and imaging techniques. Thermogravimetric analysis showed TB-COP to be thermally stable up to 380°C; while the calculated Brunauer-Emmett-Teller (BET) surface area was found to be 34 m2 g-1 at 273 K. The picric acid adsorption study of activated TB-COP showed excellent adsorption capacity of ca. 90% within 60 minutes of contact time at 298 K (Langmuir isotherm model: KL = 0.0541±6 L mg-1, R2 = 0.9962); the adsorption efficiency being shown to improve with increasing temperature. The extraction of PA was also clearly visible to the naked eye, where the yellow colored PA solution became transparent upon addition of TB-COP. Other interfering phenolic organic pollutants showed poor to moderate adsorption efficiency. Importantly, TB-COP could be used to store PA over a long period of time in a safe manner, without any leakage or any significant loss in extraction efficiency. Moreover, the polymer could be reused for several adsorption cycles, as PA could be released back into solution by simply changing the pH of the aqueous media. This makes TB-COP an extremely promising material for the selective and efficient removal of picric acid from water, as well as TB-COP can be considered as being a ‘fast’ and naked eye colorimetric indicator for such analytes.

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Publication details

The article was received on 17 Aug 2017, accepted on 09 Nov 2017 and first published on 09 Nov 2017


Article type: Paper
DOI: 10.1039/C7TA07292A
Citation: J. Mater. Chem. A, 2017, Accepted Manuscript
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    Reversible adsorption and storage of secondary explosives from water using a Tröger’s base-functionalised Polymer

    T. Gunnlaugsson, S. Shanmugaraju, D. Umadevi, A. J. Savyasachi, K. Byrne, M. Ruether, W. Schmitt and G. W. Watson, J. Mater. Chem. A, 2017, Accepted Manuscript , DOI: 10.1039/C7TA07292A

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