Issue 8, 2014

Characterization of phenomena occurring at the interface of chiral conducting surfaces

Abstract

The ability of the chiral electrode based on L-leucine functionalized terthiophene (poly(1)-Pt) to recognize and detect biomolecules has been studied as a function of hydrogen bonding between the chiral surface and a free L-leucine methyl ester. We characterized electrochemically the formation of hydrogen bonds by cyclic voltammetry (CV). The results show that the capacitive current of the chiral electrode poly(1)-Pt decreased by 30% due to hydrogen bonding between the chiral electrode and the free added L-leucine methyl ester. The origin of the hydrogen bonds on poly(1)-Pt has been confirmed by attenuated total reflection Fourier transform infrared (ATR-FTIR) using trifluoroacetic acid (CF3COOH) as free H-bonding species. The ATR-FTIR spectrum exhibits functionalities of free CF3COOH that form hydrogen bonds with the chiral conducting surface of poly(1)-Pt. Due to the insolubility of poly(1), NMR studies were performed on the parent monomers. The chemical shift of the amide proton in the 1H-NMR of the L-leucine functionalized terthiophene (1) shifted after addition of L-leucine methyl ester. Similar trends were observed for the carboxylic carbonyl of L-leucine methyl ester-terthiophene 2 in the 13C-NMR. In addition to the change in the 13C chemical shift, there is a considerable change in the spin–lattice relaxation time of the carbonyl carbon in 2 due to the formation of hydrogen bonds between the –COOH of 2 and the imidazole.

Graphical abstract: Characterization of phenomena occurring at the interface of chiral conducting surfaces

Article information

Article type
Paper
Submitted
29 Mar 2014
Accepted
14 May 2014
First published
15 May 2014

New J. Chem., 2014,38, 3379-3385

Author version available

Characterization of phenomena occurring at the interface of chiral conducting surfaces

M. Chahma, C. D. McTiernan and S. A. Abbas, New J. Chem., 2014, 38, 3379 DOI: 10.1039/C4NJ00489B

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