Pyrazoloanthrone-functionalized fluorescent copolymer for the detection and rapid analysis of nitroaromatics

Saravanan, S and Ahmad, R and Kasthuri, S and Pal, K and Raviteja, S and Nagaraaj, P and Hoogenboom, R and Nutalapati, V and Maji, S (2021) Pyrazoloanthrone-functionalized fluorescent copolymer for the detection and rapid analysis of nitroaromatics. In: Materials Chemistry Frontiers, 5 (1). pp. 238-248.

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Abstract

The development of sensors for rapid detection of chemical explosives with high sensitivity and selectivity is the focus of many research groups. In this work, we have developed a simple and straightforward synthesis of a block (co)polymer functionalized with pyrazoloanthrone (SP). The block (co)polymer was synthesized via reversible addition-fragmentation chain-transfer (RAFT) polymerization of 2-hydroxyethyl acrylate using a PEG-functionalized RAFT-agent. Subsequently, the SP was coupled to the poly(2-hydroxyethyl acrylate) block through DCC coupling. The structural and physicochemical properties of the (co)polymer were studied to explore its potential towards the detection of nitroaromatics as a model for explosives. A systematic comparison is made on the chemosensing behavior of the (co)polymer and three small molecule pyrazoloanthrone analogues with different functional groups (SP, SP-OH and SP-COOH). Fluorescence studies demonstrated a significant decrease in the fluorescence intensity of the four fluorophores in the presence of different nitroaromatics and showed unprecedented selectivity for 2,4,6 trinitrophenol (TNP). The Stern-Volmer rate constants (Ksv) of the SP-functionalized copolymer (Ksv = 9.74 � 104 M-1) showed an �3.7 times higher quenching rate constant than its monomer analog (SP) for TNP with a limit of detection (LOD) of 19 ppm. A static quenching mechanism with photoinduced electron transfer process, intermolecular hydrogen bonding and electrostatic interactions induce turn off fluorescence behavior. The interference studies with other nitroaromatics in an aqueous medium and real-time analysis in the solid-state methods demonstrate the potential of the block (co)polymer towards practical applications. © the Partner Organisations.

Item Type:	Journal Article
Publication:	Materials Chemistry Frontiers
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright to this article belongs to Royal Society of Chemistry
Keywords:	Aromatic compounds; Electron transport properties; Explosives; Fluorescence; Fluorophores; Hydrogen bonds; Physicochemical properties; Quenching; Rate constants, Fluorescence behaviors; Fluorescence intensities; Fluorescence studies; Intermolecular hydrogen bonding; Photoinduced electron-transfer process; Poly(2-hydroxyethyl acrylate); Quenching rate constant; Reversible addition-fragmentation chain transfer polymerization, Explosives detection
Department/Centre:	Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited:	02 Feb 2021 10:16
Last Modified:	02 Feb 2021 10:16
URI:	http://eprints.iisc.ac.in/id/eprint/67707

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