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Phys Chem Chem Phys. 2012 Dec 21;14(47):16229-35. doi: 10.1039/c2cp42836a. Epub 2012 Nov 8.

A redox active proton transfer and hydrogen-bonding system of tetrathiafulvalene-dicarboxylic acid and pyridine bases.

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  • 1Department of Chemistry & Key Laboratory of Organic Synthesis of Jiangsu Province, Soochow University, Suzhou 215123, P. R. China.

Abstract

Hydrogen bonds are important in supramolecular chemistry and responsible for proton transfer processes. This manuscript reports new hydrogen-bonding systems of redox-active acid-base assemblies consisting of dimethylthio-tetrathiafulvalene dicarboxylic acid (H(2)L) coupled with pyridine (py), 2,2'-bipyridine (2,2'-bpy), and 4,4'-bipyridine (4,4'-bpy). The (1)H NMR chemical shifts of the pyridines and the redox potential shifts of the tetrathiafulvalene moiety indicate that proton-transfer and strong hydrogen-bonding interactions exist between the acid and the bases in aprotic solvents. The results of cyclic voltammetry show a two-step square reaction with a redox and proton transfer coupled mechanism. The nature of the hydrogen bonds was characterized by X-ray single crystal analysis. In contrast to the mono-carboxyl-py system, in this ortho-substituted dicarboxyl-py system one proton of the H(2)L transfers completely from the carboxyl to the py group. The conjugated intramolecular and intermolecular hydrogen bonds are responsible for the proton transfer.

PMID:
23138356
[PubMed]
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