Issue 21, 2016

Self-assembled vesicle and rod-like aggregates of functionalized perylene diimide: reaction-based near-IR intracellular fluorescent probe for selective detection of palladium

Abstract

Herein, we report design, synthesis, and self-assembly of perylene diimide (PDI) based near-IR intracellular probe (PS-PDI). PS-PDI molecules undergo aggregation to form self-assembled nanospheres and nanorods morphology in THF : H2O (1 : 1) and DMSO : H2O (1 : 9), respectively. The nanospheres have an open hole on surface reminiscent of vesicle structure (with a diameter of internal void in the range of 20–25 nm) whereas lengths of the nanorods extended up to few μm range. The Pd0 based depropargylation leads to de-aggregation of these PS-PDI aggregates into smaller spherical aggregates as evidenced by DLS, SEM, and TEM studies. Interestingly, these aggregates of PS-PDI in solution show highly sensitive behavior in the presence of Pd0 showing absorbance changes in NIR region (λmax = 710 nm) and quenching of emission at λem 630 nm (DMSO : H2O, 1 : 9) with a limit of detection = 6.6 × 10−9 M or at λem 564 nm (THF : H2O, 1 : 1) with limit of detection = 2.1 × 10−8 M. Time and concentration dependent kinetics profiles of PS-PDI aggregates revealed an impressive rate constant value of 0.4 s−1 and 0.21 s−1 (DMSO : H2O, 1 : 9), respectively in fluorescence and UV-Vis spectroscopy using 2 × 10−5 M concentration of Pd0. PS-PDI undergoes rapid internalization into HeLa cells with low cytotoxicity and was successfully used as an intracellular imaging reagent for Pd0 in live HeLa cells. For practical applications, we exploited these nano-aggregates of PS-PDI for estimation of Pd2+ in the presence of a NaBH4–PPh3 mixture, Pd0 in drug and environmental samples, and Pd2+ in urine samples with excellent selectivity and sensitivity.

Graphical abstract: Self-assembled vesicle and rod-like aggregates of functionalized perylene diimide: reaction-based near-IR intracellular fluorescent probe for selective detection of palladium

Supplementary files

Article information

Article type
Paper
Submitted
27 Kol 2016
Accepted
26 Mme 2016
First published
26 Mme 2016

J. Mater. Chem. B, 2016,4, 3750-3759

Self-assembled vesicle and rod-like aggregates of functionalized perylene diimide: reaction-based near-IR intracellular fluorescent probe for selective detection of palladium

P. Singh, L. S. Mittal, V. Vanita, K. Kumar, A. Walia, G. Bhargava and S. Kumar, J. Mater. Chem. B, 2016, 4, 3750 DOI: 10.1039/C6TB00512H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements