Tetrathiafulvalenophanes and their catenanes

Abstract

Monomacrocycles of the two electron donors tetrathiafulvalene (TTF) and 1,5-dioxynaphthalene have been prepared, together with three symmetric TTF-containing bismacrocycles, two of which have been prepared by a two-step deprotection–cyclization approach. By utilizing the donor–acceptor interactions of these donors with the dipyridinium dication of 1,1′-[1,4-phenylenebis(methylene)]bis-4,4′-bipyri dinium bis(hexafluorophosphate), [2]catenanes were synthesized. In the case of one of the bismacrocycles it was possible to isolate a minor amount of a bis[2]catenane. The catenanes were characterized by ¹ H NMR spectroscopy, electrospray mass spectroscopy (ESMS) and their fragmentation in the gas phase was also analysed by collisional activation (ESMS/MS). Also, one tetramacrocyclic compound, the first TTF-based ribbon compound, has been synthesized. This compound shows complex electrochemical properties.