Self-assembling, chromogenic receptors for the recognition of dicarboxylic acids

M. Scott Goodman, Andrew Hamilton, Jean Weiss

Research output: Contribution to journalArticle

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- and Cu(2)2+BF4-. These orange Cu(I) complexes are shown to bind (Ka > 104 M-1) to a variety of dicarboxylic acids in chloroform, with a slight preference for the C5-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- and 2:1 complexes for Cu(2)2+BF4-, with the dicarboxylic acid substrate hydrogen bonding simultaneously to an acylaminopyridine binding site on each ligand. For Cu(2)2+BF4-, 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 change in the receptors resulting from hydrogen bond formation with the substrate.

Original languageEnglish (US)
Pages (from-to)8447-8455
Number of pages9
JournalJournal of the American Chemical Society
Volume117
Issue number32
StatePublished - Aug 16 1995

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Chromogenics
Dicarboxylic Acids
Acids
Substrates
Ligands
Complexation
Binding sites
Hydrogen bonds
Bearings (structural)
Binding Sites
Glutamates
Phenanthrolines
Chemical shift
Hydrogen Bonding
Chloroform
Absorption spectra
Hydrogen
Chlorine compounds
Color
Nuclear magnetic resonance

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Self-assembling, chromogenic receptors for the recognition of dicarboxylic acids. / Goodman, M. Scott; Hamilton, Andrew; Weiss, Jean.

In: Journal of the American Chemical Society, Vol. 117, No. 32, 16.08.1995, p. 8447-8455.

Research output: Contribution to journalArticle

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