Dynamic switching between binding sites in the complexation of macrocyclic 'push-pull' chromophores to lanthanides

被引:13
作者
Coluccini, Carmine [1 ]
Pasini, Dario [1 ]
Righetti, Pierpaolo [1 ,2 ]
Griend, Douglas A. Vander [2 ]
机构
[1] Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
[2] Calvin Coll, Dept Chem & Biochem, Grand Rapids, MI 49546 USA
关键词
Macrocycles; Lanthanides; Hill equation; 'Push-pull' chromophores; Factor analysis; Spectrophotometric titration; Sivvu; BUILDING-BLOCKS; COOPERATIVITY; LIGAND; EXTTF;
D O I
10.1016/j.tet.2009.10.024
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
The introduction of a 1,3-diacetylpyridine moiety, as an additional binding niche in a macrocyclic receptor ligand containing a conjugated, push-pull malonate functionality, leads to, in addition to the 1:1 binding stoichiometry, the equilibrium formation of multiple complexes, specifically 1:2, 2:1, and 3:1 ligand:metal complexes with lanthanide trications. Various binding modes elicit distinctive responses in the visible region, which enhance the potential recognition of lanthanide ions. This paper also highlights the usefulness of a full factor analysis in the elucidation of complex binding phenomena. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10436 / 10440
页数:5
相关论文
共 30 条
[1]
Lanthanide(III) chelates for NMR biomedical applications [J].
Aime, S ;
Botta, M ;
Fasano, M ;
Terreno, E .
CHEMICAL SOCIETY REVIEWS, 1998, 27 (01) :19-29
[2]
Taking advantage of luminescent lanthanide ions [J].
Bünzli, JCG ;
Piguet, C .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (12) :1048-1077
[3]
PROBE-DEPENDENT COOPERATIVITY PATTERNS IN HILL-PLOTS [J].
BYERS, LD .
JOURNAL OF CHEMICAL EDUCATION, 1977, 54 (06) :352-354
[4]
Methanofullerenes from macrocyclic malonates [J].
Carano, M ;
Corvaja, C ;
Garlaschelli, L ;
Maggini, M ;
Marcaccio, M ;
Paolucci, F ;
Pasini, D ;
Righetti, PP ;
Sartori, E ;
Toffoletti, A .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (02) :374-384
[5]
Luminescent lanthanide complexes of a bis-bipyridine-phosphine-oxide ligand as tools for anion detection [J].
Charbonnière, LJ ;
Ziessel, R ;
Montalti, M ;
Prodi, L ;
Zaccheroni, N ;
Boehme, C ;
Wipff, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (26) :7779-7788
[6]
Push-Pull supramolecular chromophores supported on cyclopolymers [J].
Coluccini, Carmine ;
Metrangolo, Pierangelo ;
Parachini, Marco ;
Pasini, Dario ;
Resnati, Giuseppe ;
Righetti, Pierpaolo .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (15) :5202-5213
[7]
Pyridine-2,6-bis(oxazolines), helpful ligands for asymmetric catalysts [J].
Desimoni, G ;
Faita, G ;
Quadrelli, P .
CHEMICAL REVIEWS, 2003, 103 (08) :3119-3154
[8]
Assessment of cooperativity in self-assembly [J].
Ercolani, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (51) :16097-16103
[9]
Large exTTF-Based dendrimers. self-assembly and peripheral cooperative multiencapsulation of C60 [J].
Fernandez, Gustavo ;
Sanchez, Luis ;
Perez, Emilio M. ;
Martin, Nazario .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) :10674-10683
[10]
Garlaschelli L, 2002, EUR J ORG CHEM, V2002, P3385