Crown Ether Annelated Tetrathiafulvalenes. 2

Article abstract of DOI:10.1021/jo00058a013

A synthetic procedure leading to derivatives of tetrathiafulvalene (TTF) incorporating polyether chains of various lengths, some nitrogen analogs, and a 2,6-bis(methylene)pyridine analog has been developed.These compounds possess cage-type structures which were confirmed by X-ray crystallography in four cases, two of which are reported herein for the first time.Structural and electronic features of these cage molecules were correlated to oxidation potentials by the use of semiempirical methods (MNDO-PM3).An investigation of the alkali metal ion affinity using PDMS revealed that these compounds are poor ligands.Finally, in one case, protonation of the core TTF was studied by NMR.