Amino acid derivatives of tetrathiafulvalene and their N- H···O peptide bond dipoles-templated solid state assemblies

Abstract

We report on a series of amino acid derivatives of tetrathiafulvalene as well as on the structure-directing abilities of their peptide residues in the crystalline solid state to stabilize patterns of interactions such as β strands and sheet motifs. Characteristic hydrogen-bonding motifs are indeed identified within ethylenedithiotetrathiafulvalene (EDT-TTF) and dimethyltetrathiafulvalene (Me2-TTF) based compounds 1-5. Esters 1-3 contain hydrogen-bond acceptors, namely carbonyl groups, as well as one strong (NH) and one weak (C sp 2-H) hydrogen-bond donor. In addition to the hydrogen-bonded sets of ester derivatives, acids 4 and 5 present the carboxylic acid moiety, which acts as both a hydrogen-bond donor and acceptor. EDT-TTF-CO-GlyOH has been previously used to afford a new type of hydrogen-bonded acid/zwitterion (1:1) hybrid admixture of redox peptidics. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.