Issue 22, 2017

Axially chiral amino acid scaffolds as efficient fluorescent discriminators of methanol–ethanol

Abstract

We report a unique fluorescence sensor based on an axially chiral unnatural triazolyl aromatic amino acid scaffold (ArTAA) for discrimination of methanol from ethanol via a switch on fluorescence response. All three sensors, the simple scaffold (ArTAA), and the mono- (PyAm-ArTAA) and bis-pyrenyl- (Py2Am-ArTAA) amides, show similar sensitivity and detection limit ranging from 0.5–2.1 v/v% of ethanol. The solid films of these sensors are also found to be effective in sensing ethanol vapour via generation of a distinct and enhanced fluorescence signal. All our experimental results suggest the role of axial chirality of the hairpin-shaped scaffold in differential solvation guided H-bonding interaction and discriminating between ethanol and methanol with a switch-on fluorescence response.

Graphical abstract: Axially chiral amino acid scaffolds as efficient fluorescent discriminators of methanol–ethanol

Supplementary files

Article information

Article type
Paper
Submitted
02 Jun 2017
Accepted
05 Oct 2017
First published
05 Oct 2017

New J. Chem., 2017,41, 13391-13398

Axially chiral amino acid scaffolds as efficient fluorescent discriminators of methanol–ethanol

S. S. Bag and S. Jana, New J. Chem., 2017, 41, 13391 DOI: 10.1039/C7NJ01945A

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