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

✍ Scribed by Beatriz M. Illescas; José Santos; Marta C. Díaz; Nazario Martín; Carmen M. Atienza; Dirk M. Guldi

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 294 KB
• Volume: 2007
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200700226

✦ Synopsis

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)