CONVERGENT SYNTHESIS OF RIGID MACROCYCLES CONTAINING ONE OR 2 TETRATHIAFULVALENE UNITS

The synthesis of rigid tetrathiafulvalenenophanes containing one or tw o tetrathiafulvalene units is presented, together with a stepwise conv ergent synthesis of macrocyclic bis-tetrathiafulvalenes via several op en dimeric tetrathiafulvalenes. These systems were investigated by cyc lic voltammetry, which revealed that intramolecular interaction betwee n the electroactive units only took place if the units were fixed in a rigid conformation. The X-ray structure of 10a confirmed the cis conf iguration of a concave molecule, which is packed in antiparallel stack s.