Issue 19, 2018

A ratiometric hypochlorite sensor guided by PET controlled ESIPT output with real time application in commercial bleach

Abstract

A HydroxyBenzothiazolyl dihydroPyrazole conjugate (HBP) featuring a modified acetylphenylhydrazine species armed with an N–N single bond forbidden from rotating was designed and employed for the sensitive and selective detection of hypochlorite (OCl) anion. The probe exhibited weak fluorescence on account of photoinduced electron transfer (PET) from hydroxyphenyl dihydropyrazole moiety to benzothiazole which promptly changed upon OCl induced oxidation of the dihydropyrazole species to pyrazole enhancing excited state intramolecular proton transfer (ESIPT) in the hydroxybenzothiazole counterpart. This led to excellent ratiometric fluorescence changes in the probe that conclusively proved its effectiveness at sensing OCl. This unique, specific and fast oxidation was achieved selectively by OCl as evidenced by competition experiments with various other reactive oxygen species (ROS), reactive nitrogen species (RNS) and anions. The mechanism has been supported by 1H-NMR titration studies along with DFT calculations. Notably, the probe responded remarkably to hypochlorite present in commercial bleach. Finally, the probe proved amenable to OCl sensing in living matrices with no interference from trace amounts of ROS and RNS that inhabit living cells.

Graphical abstract: A ratiometric hypochlorite sensor guided by PET controlled ESIPT output with real time application in commercial bleach

Supplementary files

Article information

Article type
Paper
Submitted
06 Jul 2018
Accepted
03 Sep 2018
First published
03 Sep 2018

New J. Chem., 2018,42, 15990-15996

A ratiometric hypochlorite sensor guided by PET controlled ESIPT output with real time application in commercial bleach

A. Gangopadhyay, S. S. Ali, U. N. Guria, S. K. Samanta, R. Sarkar, P. Datta and A. K. Mahapatra, New J. Chem., 2018, 42, 15990 DOI: 10.1039/C8NJ03369B

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