Catechol-appended TTF derivatives

Abstract

abstract EDT-TTF-CONHCatOH, a catechol-appended TTF derivative, 5 was synthesized through a straightforwardstrategy. The electronic absorption and the electrochemical investigations as well as molecular orbitalcalculations for compounds 4 and 5 have been performed. The electrochemical measurements of 5 indi-cate that it is a suitable candidate for the formation of zwitterionic molecular solids and also two-com-ponent radical cation salts. The crystal structure of compound 5 reveals supramolecular dimersassembled via a set of O–H O hydrogen bonds between the catechol and amide units. 2013 Elsevier Ltd. All rights reserved. Tetrathiafulvalene (TTF) and its many derivatives have been thesubject of numerous studies due to their use as precursors formolecular conductors and superconductors. 1 This is mainly dueto their strong electron donating which results in two sequentialand reversible oxidation processes, affording radical cation (TTF + )and dication (TTF 2+ ) species. 2 It is well known that intermolecularinteractions play a significant role in controlling the electronicstate, molecular arrangements, and solid-state physical propertiesof these crystalline materials. Thus, efforts have been devoted todirect the intermolecular interactions in both the neutral, closed-shell molecules as well as in the corresponding charge transfercomplexes and radical cation salts.