Issue 10, 2016

Novel pyrene containing monomeric and dimeric supramolecular AIEE active nano-probes utilized in selective “off–on” trivalent metal and highly acidic pH sensing with live cell applications

Abstract

Two novel pyrene containing monomeric and dimeric Schiff base derivatives PCS1 and PCS2 have been synthesized via one-pot reaction and their nano-J-type aggregation induced emission enhancement (AIEE) was well demonstrated using UV-Vis/PL, transmission electron microscopy (TEM), dynamic light scattering (DLS), time resolved photoluminescence (TRPL), and live cell imaging studies. In contrast to PCS2, PCS1 in CH3CN exhibits fluorescence “off–on” sensor selectivity towards transition trivalent metal ions (Fe3+, Cr3+ and Al3+) among other metals, via PET inhibition with excimer PCS1–PCS1* formation. The 2 : 1 stoichiometry of PCS1⋯M3+ (M = Fe/Cr/Al) sensor complexes was calculated from Job's plots based on their PL titrations. In addition, the binding sites of PCS1⋯M3+ sensor complexes were well recognised from the 1H NMR titrations and supported by ESI(+ve) mass and FTIR analysis. Additionally, fluorescence reversibilities of PCS1⋯M3+ were observed via consequent addition of M3+ ions and PMDTA, respectively. Furthermore, the detection limits (LODs) and the association constant (Ka) values of PCS1⋯M3+ complexes were calculated using standard deviation and linear fittings. Likewise, quantum yield (Φ) measurements, TEM analysis, determination of the effect of pH, density functional theory (DFT) and time resolved photoluminescence (TRPL) studies were performed for the PCS1⋯M3+ sensor complexes. More importantly, confocal fluorescence microscopy imaging of Raw264.7 cells showed that PCS1 could be used as an effective fluorescent probe for detecting transition trivalent metal ions (Fe3+, Cr3+, and Al3+) in living cells. Impressively, both PCS1 and PCS2 showed “off–on” sensing at highly acidic pH values (1–3) with live cell applications.

Graphical abstract: Novel pyrene containing monomeric and dimeric supramolecular AIEE active nano-probes utilized in selective “off–on” trivalent metal and highly acidic pH sensing with live cell applications

Supplementary files

Article information

Article type
Paper
Submitted
10 Nov 2015
Accepted
08 Feb 2016
First published
08 Feb 2016

J. Mater. Chem. C, 2016,4, 2056-2071

Author version available

Novel pyrene containing monomeric and dimeric supramolecular AIEE active nano-probes utilized in selective “off–on” trivalent metal and highly acidic pH sensing with live cell applications

M. Shellaiah, T. Simon, V. Srinivasadesikan, C. Lin, K. W. Sun, F. Ko, M. Lin and H. Lin, J. Mater. Chem. C, 2016, 4, 2056 DOI: 10.1039/C5TC03738G

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