Tautomerism as primary signaling mechanism in metal sensing: the case of amide group

The concept for sensing systems using the tautomerism as elementary signaling process has been further developed by synthesizing a ligand containing 4-(phenyldiazenyl)naphthalene-1-ol as a tautomeric block and an amide group as metal capturing antenna. Although it has been expected that the intramol...

Full description

Saved in:
Bibliographic Details
Published in:Beilstein journal of organic chemistry 2019-08, Vol.15 (1), p.1898-1906
Main Authors: Deneva, Vera, Dobrikov, Georgi, Crochet, Aurelien, Nedeltcheva, Daniela, Fromm, Katharina M, Antonov, Liudmil
Format: Article
Language:English
Subjects:
amide group
azo dye
Chemistry
Equilibrium
Full Research Paper
Hydrogen
Hydrogen bonding
Ligands
Metal ions
molecular sensor
Naphthalene
sidearm
Solvents
Tautomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The concept for sensing systems using the tautomerism as elementary signaling process has been further developed by synthesizing a ligand containing 4-(phenyldiazenyl)naphthalene-1-ol as a tautomeric block and an amide group as metal capturing antenna. Although it has been expected that the intramolecular hydrogen bonding (between the tautomeric hydroxy group and the nitrogen atom from the amide group) could stabilize the pure enol form in some solvents, the keto tautomer is also observed. This is a result from the formation of intramolecular associates in some solvents. Strong bathochromic and hyperchromic effects in the visible spectra accompany the 1:1 formation of complexes with some alkaline earth metal ions.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.15.185