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Quinoline‐Containing Calixarene Fluoroionophores: A Combined NMR, Photophysical and Modeling Study
Author(s) -
Casnati Alessandro,
Sansone Francesco,
Sartori Andrea,
Prodi Luca,
Montalti Marco,
Zaccheroni Nelsi,
Ugozzoli Franco,
Ungaro Rocco
Publication year - 2003
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.200390206
Subject(s) - chemistry , calixarene , quinoline , lanthanide , chromophore , acetonitrile , pyridine , metalation , metal ions in aqueous solution , alkoxy group , ligand (biochemistry) , photochemistry , inorganic chemistry , metal , stereochemistry , ion , medicinal chemistry , molecule , organic chemistry , biochemistry , alkyl , receptor
The 8‐alkoxy‐5‐chloroquinoline fluorophore was appended at the lower rim of a calix[4]arene triamide with two different orientations. In ligand 1 the quinoline part is linked to the calixarene skeleton through the pyridine C 2 atom, while in 2 it is linked through the phenolic oxygen atom of the chromophore. The binding properties of both ligands, investigated in chloroform and methanol solutions, indicate that they are efficient fluoroionophores, with selectivity for sodium and strontium ions among alkali and alkaline earth metal ions. Combined NMR, photophysical, and modeling studies disclosed the peculiar conformational and coordination features of monovalent and divalent metal ion complexes. Lanthanide metal ion complexes were prepared and studied in acetonitrile solution showing good luminescence in the case of Nd 3+ , Yb 3+ , and Er 3+ ions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)