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Lanthanide Complexes of Polyacid Ligands derived from 2, 6‐bis(pyrazol‐1‐yl)pyridine, pyrazine, and 6, 6′‐bis(pyrazol‐1‐yl)‐2, 2′‐bipyridine: Synthesis and luminescence properties
Author(s) -
RodriguezUbis Juan Carlos,
Sedano Rosa,
Barroso Gemma,
Juanes Olga,
Brunet Ernesto
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800108
Subject(s) - chemistry , pyrazine , pyridine , acetic acid , lanthanide , luminescence , pyrazole , bipyridine , medicinal chemistry , 2,2' bipyridine , molecule , stereochemistry , crystallography , ion , crystal structure , organic chemistry , physics , optoelectronics
Abstract The synthesis of three novel pyrazole‐containing complexing acids, N,N,N′,N ′‐{2, 6‐bis[3‐(aminomethyl)pyrazol‐1‐yl]‐4‐methoxypyridine}tetrakis(acetic acid)( 1 ), N,N,N ′, N ′‐{2, 6‐bis[3‐(aminomethyl)pyrazol‐1‐yl]pyrazine}‐tetrakis(acetic acid) ( 2 ), and N,N,N ′, N ′‐{6, 6′‐bis[3‐(aminomethyl)pyrazol‐1‐yl]‐2, 2′‐bipyridine}tetrakis(acetic acid) ( 3 ) is described. Ligands 1–3 formed stable complexes with Eu III , Tb III , Sm III , and Dy III in H 2 O whose relative luminescence yields, triplet‐state energies, and emission decay lifetimes were measured. The number of H 2 O molecules in the first coordination sphere of the lanthanide ion were also determined. Comparison of data from the Eu III and Tb III complexes of 1–3 and those of the parent trisheterocycle N,N,N ′, N ′‐{2, 6‐bis[3‐(aminomethyl)pyrazol‐l‐yl]pyridine}tetrakis(acetic acid) showed that the modification of the pyridine ring for pyrazine or 2, 2′‐bipyridine strongly modify the luminescence properties of the complexes. MeO Substitution at C(4) of 1 maintain the excellent properties described for the parent compound and give an additional functional group that will serve for attaching the label to biomolecules in bioaffinity applications.