Supramolecular Threaded Complexes from Fullerene–Crown Ether and π‐Extended TTF Derivatives

Abstract

Abstract A series of π‐extended TTFs (exTTFs) bearing one ( 8 , 16 , 19 ) or two ( 14 ) dibenzylammonium units have been threaded through a dibenzo‐24‐crown‐8 (DB24C8) ring covalently linked to a C 60 sphere. Whereas 8 and 14 were prepared in a multistep synthetic procedure involving Sonogashira cross‐coupling reactions affording rigid donors, exTTFs 16 and 19 were prepared by direct esterification reactions leading to more flexible systems. Complexation experiments carried out by 1 H NMR titration and fluorescence studies show the formation of stable supramolecular dyads with binding constants ranging from 10 3 to 10 4 M –1 . Although the UV/Vis and CV studies reveal the lack of interaction between the electroactive species (C 60 and exTTF) in the ground state, fluorescence data indicate the presence of an electronic interaction in the excited state. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)