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Synthesis of Homo‐ and Heteroditopic 8‐Hydroxyquinoline Ligands
Author(s) -
Albrecht Markus,
Osetska Olga,
Fröhlich Roland
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.200700513
Subject(s) - chemistry , claisen rearrangement , quinoline , supramolecular chemistry , metathesis , ligand (biochemistry) , salt metathesis reaction , aryl , chelation , 8 hydroxyquinoline , stereochemistry , ether , combinatorial chemistry , organic chemistry , molecule , polymerization , alkyl , biochemistry , receptor , polymer
Abstract The Claisen rearrangement is a versatile reaction for the preparation of either isobutenylidene‐ or n ‐butenylidene‐bridged bis(8‐hydroxyquinoline) ligands for supramolecular chemistry. The Hiratani–double‐Claisen rearrangement of the appropriate isobutenylidene bis(aryl) ethers enables the formation of either symmetrical or unsymmetrical ligand systems with two tridentate or one bi‐ and one tridentate quinoline‐based chelating units. Claisen rearrangement of quinoline allyl ether followed by Grubbs metathesis affords the symmetric ligand with an elongated spacer between the chelates. The described ligands are of interest for the self‐assembly of homo‐ and heterodinuclear near‐IR‐emitting lanthanide complexes.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)