Amine detection with distyrylbenzenedialdehyde-based Knoevenagel adducts.
J Org Chem
; 80(10): 5159-66, 2015 May 15.
Article
em En
| MEDLINE
| ID: mdl-25867674
ABSTRACT
Eight acceptor-substituted distyrylbenzene (DSB) derivatives were obtained by postfunctionalization of dialdehyde precursor 1 using Knoevenagel condensation. Solubility in a water/THF 91 mixture was achieved through the addition of branched oligoethylene glycol side chains. The acceptor compounds discriminate primary and secondary amines in aqueous solution. The fluorescence responses were analyzed by the multivariate analysis of variance (MANOVA) protocol, a statistical tool. In contrast to 1, the adducts show reactivity toward secondary and aromatic amines. Nitroolefin 2f is the most active dosimeter molecule. Reaction with amines is completed after less than 3 min, and the limit of detection (LOD) is improved by a factor of 10. Propylenediamine can be detected at 75 µM. This is a 10-fold improvement for the detection limit when compared to the detection limit of the starting dialdehyde.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Tipo de estudo:
Diagnostic_studies
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2015
Tipo de documento:
Article