Issue 4, 2020

Near-IR oxime-based solvatochromic perylene diimide probe as a chemosensor for Pd species and Cu2+ ions in water and live cells

Abstract

A near-IR perylene diimide probe (OPR-PDI) containing an oxime-propargyl hybrid moiety at the bay position, was designed and synthesized for detection of Pd species and Cu2+ ions in 90% water, the solid state and MG-63 live cells. The aggregation tendency of OPR-PDI in different polarity solvents transmits solvatochromic and fluorochromic properties to differentiate certain organic solvents. Supramolecular aggregates of OPR-PDI in 90% water act as a dual chemosensor for palladium (Pd) species via de-propargylation or hydrolysis of the Schiff-base and Cu2+ ions via complexation with the O/N binding site with a low limit of detection (LOD) of the order of 7.9 × 10−8 M and 3.4 × 10−7 M respectively. TLC strips coated with OPR-PDI can be applied for sensing of Pd0 and Cu2+ ions in the solid state at levels as low as 34.6 ng cm−2 and 10.5 ng cm−2. OPR-PDI imprinted TLC strips could be used as paper sheets for writing coloured alphabets using Pd0 and Cu2+ ions as ink. Moreover, MTT assay showed that OPR-PDI has very low cytotoxicity (IC50 = 230 μM), good permeability, biocompatibility and can be applied for bio-imaging of Pd species and Cu2+ ions in MG-63 cells. DFT calculations, and cyclic voltammetric (CV) and NMR titration studies have also been discussed.

Graphical abstract: Near-IR oxime-based solvatochromic perylene diimide probe as a chemosensor for Pd species and Cu2+ ions in water and live cells

Supplementary files

Article information

Article type
Paper
Submitted
19 Dec 2019
Accepted
07 Mar 2020
First published
10 Mar 2020

Photochem. Photobiol. Sci., 2020,19, 504-514

Near-IR oxime-based solvatochromic perylene diimide probe as a chemosensor for Pd species and Cu2+ ions in water and live cells

P. Sharma, S. Kaur, S. Kaur and P. Singh, Photochem. Photobiol. Sci., 2020, 19, 504 DOI: 10.1039/C9PP00487D

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