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Titolo:
SELF-ASSEMBLING, CHROMOGENIC RECEPTORS FOR THE RECOGNITION OF DICARBOXYLIC-ACIDS
Autore:
GOODMAN MS; HAMILTON AD; WEISS J;
Indirizzi:
UNIV PITTSBURGH,DEPT CHEM PITTSBURGH PA 15260 UNIV PITTSBURGH,DEPT CHEM PITTSBURGH PA 15260 UNIV STRASBOURG 1,INST LE BEL,CNRS,URA 405 F-67000 STRASBOURG FRANCE
Titolo Testata:
Journal of the American Chemical Society
fascicolo: 32, volume: 117, anno: 1995,
pagine: 8447 - 8455
SICI:
0002-7863(1995)117:32<8447:SCRFTR>2.0.ZU;2-U
Fonte:
ISI
Lingua:
ENG
Soggetto:
CONVERGENT FUNCTIONAL-GROUPS; CHARGE-TRANSFER ABSORPTION; MOLECULAR RECOGNITION; SYNTHETIC RECEPTOR; PHOTOPHYSICAL PROPERTIES; METAL-CATIONS; BINDING; COMPLEX; COPPER(I); DERIVATIVES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
67
Recensione:
Indirizzi per estratti:
Citazione:
M.S. Goodman et al., "SELF-ASSEMBLING, CHROMOGENIC RECEPTORS FOR THE RECOGNITION OF DICARBOXYLIC-ACIDS", Journal of the American Chemical Society, 117(32), 1995, pp. 8447-8455

Abstract

The synthesis of ligands (2,9-disubstituted phenanthrolines) bearing one or two acylaminopyridine binding sites, compounds 1 and 2 respectively, is described. Each ligand can assemble on a Cu(I) template, forming two different receptors for dicarboxylic acids, Cu(1)(2)(BF4-)-B-and Cu(2)(2)(BF4-)-B-+. These orange Cu(I) complexes are shown to bind (K-a > 10(4) M(-1)) to a variety of dicarboxylic acids in chloroform, with a slight preference for the C-5-dicarboxylic acids, glutaric and N-CBz-glutamic acids, over shorter and longer substrates. Complexation is analyzed both by NMR chemical shift changes and UV-visible absorption changes. The data indicate formation of 1:1 complexes for Cu(1)(2)(BF4-)-B-+ and 2:1 complexes for Cu(2)(2)(BF4-)-B-+, with the dicarboxylic acid substrate hydrogen bonding simultaneously to an acylaminopyridine binding site on each ligand. For Cu(2)(2)(BF4-)-B-+, the complexation event results in large shifts in the visible absorption bands and a color change from orange to red. The change in the visible absorbance, and therefore the chromogenicity, was found to be substrate dependent. The chromogenic effect is explained by a conformational changein the receptors resulting from hydrogen bond formation with the substrate.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 01:33:55