New Macrobicycles Containing a Tetralactam Moiety: Template Synthesis and Study of their Binding with Lanthanides

The synthesis of macrobicyclic cryptands 1, 2 from an 18-membered diazatetralactam and 6,6′-bis(bromomethyl)-2,2′-bipyridine or 2,6-bis(3-bromomethyl-1-pyrazolyl)pyridine has been investigated using various metal carbonates. The analysis of the distribution products by gel permeation chromatography...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 17; pp. 2673 - 2681
Main Authors Azéma, Joëlle, Galaup, Chantal, Picard, Claude, Tisnès, Pierre, Ramos, Patricia, Juanes, Olga, Rodrı́guez-Ubis, Juan Carlos, Brunet, Ernesto
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.04.2000
Elsevier
Subjects
amides
Chemistry
Chemistry, Organic
cryptands
lanthanides
Physical Sciences
Science & Technology
template effects
amides
cryptands
template effects
lanthanides
2,2'-BIPYRIDINE
NUCLEAR-MAGNETIC-RESONANCE
HYDROLYSIS
LUMINESCENCE PROPERTIES
COORDINATION
ELECTROSPRAY MASS-SPECTROMETRY
EUROPIUM(III) COMPLEXES
LIGANDS
DIAZATETRALACTAMS
UNITS
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Summary:The synthesis of macrobicyclic cryptands 1, 2 from an 18-membered diazatetralactam and 6,6′-bis(bromomethyl)-2,2′-bipyridine or 2,6-bis(3-bromomethyl-1-pyrazolyl)pyridine has been investigated using various metal carbonates. The analysis of the distribution products by gel permeation chromatography showed that macrocyclization process was markedly conditioned by cation template effects. Optimum yields were obtained for Li + and Na + in the preparation of 1 and 2, respectively. The cryptate structure of the corresponding complexes of Ln(III) (Ln=Eu, Tb, Gd) is discussed on the basis of spectroscopic and photophysical data.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00164-2