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Fullerene Ylidene Malonate Supramolecular Triads
Author(s) -
Garlaschelli Luigi,
Messina Ivano,
Pasini Dario,
Righetti Pier Paolo
Publication year - 2002
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 - 10.1002/1099-0690(200210)2002:20<3385::aid-ejoc3385>3.0.co;2-v
Subject(s) - chemistry , malonate , dimethyl malonate , supramolecular chemistry , moiety , diethyl malonate , benzaldehyde , knoevenagel condensation , cyclohexenone , malonic acid , aldol condensation , polymer chemistry , organic chemistry , molecule , enantioselective synthesis , catalysis
This paper describes the synthesis and characterization of novel covalently bound fullerene ylidene malonate dyads in which the linker between the two units is a di‐, tri‐, or tetraethylene glycol unit. The synthesis involves a stepwise, convergent addition of the two components to bis(malonate crown ethers) of increasing overall dimensions through (i) Knoevenagel condensation with (dimethylamino)benzaldehyde and (ii) subsequent Bingel functionalization of the free malonate moiety with C 60 . These dyads have been spectroscopically characterized and studied by UV/Vis spectroscopy. Their ability to form stable complexes with europium triflate, thus forming a complex three‐component supramolecular system with UV/Vis absorption characteristics clearly dependent on the overall distance between the interacting units, has been assessed quantitatively. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)