Issue 4, 2017

Fluorescein hydrazone-based supramolecular architectures, molecular recognition, sequential logic operation and cell imaging

Abstract

A fluorescein hydrazone (FDNS) is prepared by the coupling of fluorescein hydrazide with 3,5-dinitrosalicylaldehyde. It is well characterized using spectroscopic (IR, UV-visible, 1H, 13C NMR, ESI-MS) techniques and X-ray crystallography. FDNS is embedded with several H-bonding domains which provide interesting intra and inter molecular H-bonded networks. Its crystal packing along the b crystallographic axis using H-bonding interactions provides a fascinating helical structure. It detects Cu2+ ions selectively over many relevant ions and displays a novel peak at λmax = 495 nm. The significant enhancement in its fluorescence is observed with a peak at λem = 517 nm on addition of Hg2+ ions, which is quenched upon the addition of S2− ions. The sensing of Hg2+ ions by FDNS follow a hydrolysis pathway whereas the binding of Cu2+ ions with FDNS provides a colour change. The addition of a solution of tetrabutylammoniumcyanide in methanol to a corresponding solution of FDNS caused a turn to a green colour immediately. But on keeping the solution at room temperature for 72 h, red coloured crystals are obtained. The crystals were authenticated by X-ray crystallography. It was found to be a new compound FKCN in which a tetrabutylammonium cation is co-crystallized with deprotonated FDNS. Its supramolecular assembly via H-bonding provides an interesting ladder type architecture. FDNS displays chronological logic gate-based detection of several ions (Cu2+, Hg2+, EDTA, and S2−) at ppm levels. The real sample analysis, live cell imaging and portable paper strip based detection of Cu2+ and Hg2+ ions via an obvious colour change endows FDNS with great economic significance in recognition processes.

Graphical abstract: Fluorescein hydrazone-based supramolecular architectures, molecular recognition, sequential logic operation and cell imaging

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
03 nov 2016
Accepted
01 dez 2016
First published
12 jan 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 2264-2272

Fluorescein hydrazone-based supramolecular architectures, molecular recognition, sequential logic operation and cell imaging

K. Tripathi, A. Rai, A. K. Yadav, S. Srikrishna, N. Kumari and L. Mishra, RSC Adv., 2017, 7, 2264 DOI: 10.1039/C6RA26255D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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