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Supramolecular Threaded Complexes from Fullerene–Crown Ether and π‐Extended TTF Derivatives
Author(s) -
Illescas Beatriz M.,
Santos José,
Díaz Marta C.,
Martín Nazario,
Atienza Carmen M.,
Guldi Dirk M.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700226
Subject(s) - chemistry , supramolecular chemistry , sonogashira coupling , crown ether , fullerene , fluorescence , titration , covalent bond , excited state , polymer chemistry , ether , proton nmr , stereochemistry , photochemistry , organic chemistry , molecule , ion , palladium , physics , quantum mechanics , nuclear physics , catalysis
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)