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Arylene-vinylene Terpyridine Conjugates: Highly Sensitive, Reusable and Simple Fluorescent Probes for the Detection of Nitroaromatics

Abstract

A series of highly emissive arylene-vinylene conjugated 4'-(4-{2-[aryl]-ethenyl}phenyl)-2,2':6',2''-terpyridines (aryl = 4-methylphenyl, 4-fluorophenyl, 1-naphthyl, and 9-anthralyl in P1-P4 respectively) have been explored for the detection of nitroaromatic compounds (NACs). The synthesized push-pull fluorescent probes show remarkable sensitivity towards NACs in solution, vapor and contact mode as ‘turn-off’ sensor which can be visualized by naked eye. The photophysical studies reveal that the electron transfer occurs from the electron rich arylene-vinylene conjugated terpyridine to the electron deficient NACs through supramolecular complexation which is further illustrated from the time-resolved fluorescence and 1H NMR titration experiment. The arylene-vinylene conjugated terpyridines offer excellent sensitivity towards picric acid (PA) exhibiting nanomolar detection in contact mode, and ppm level detection in solution state with association constants in the range of 2.54-8.08×104 M-1. The HOMO-LUMO energy levels have been calculated from electrochemical and TDDFT studies to understand the efficacy and the mechanism of electron transfer from probe to NACs leading to fluorescence quenching. The reversibility, recyclability and contact mode detection of PA in nanomolar level demonstrates its practical utility as solid state kit for onsite detection of NAC explosives.

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Publication details

The article was received on 12 Sep 2017, accepted on 10 Oct 2017 and first published on 11 Oct 2017


Article type: Paper
DOI: 10.1039/C7TC04178K
Citation: J. Mater. Chem. C, 2017, Accepted Manuscript
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    Arylene-vinylene Terpyridine Conjugates: Highly Sensitive, Reusable and Simple Fluorescent Probes for the Detection of Nitroaromatics

    A. Sil, D. Giri and S. K. Patra, J. Mater. Chem. C, 2017, Accepted Manuscript , DOI: 10.1039/C7TC04178K

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