The Influence of the Amide Linkage in the Fe-III-Binding Properties of Catechol-Modified Rosamine Derivatives

• Tipo: Artigo em Revista Científica Internacional
• Data: 2015

Autores

Queiros, C (Autor) Outra; Leite, A (Autor) Outra; Couto, MGM (Autor) Outra; Cunha Silva, L (Autor) FCUP; Barone, G (Autor) Outra; de Castro, B (Autor) FCUP; Maria Rangel (Autor) ICBAS; Silva, AMN (Autor) Outra; Silva, AMG (Autor) Outra

Revista

Título: Chemistry - A European Journal

Vol. 21

Páginas: 15692-15704

ISSN: 0947-6539

Editora: Wiley-Blackwell

Indexação

ISI Web of Knowledge - 8 Citações

Scopus - 8 Citações

Outras Informações

ID Authenticus: P-00G-TBJ

DOI: 10.1002/chem.201502093

Abstract (EN): The two new fluorescent ligands RosCat1 and RosCat2 contain catechol receptors connected to rosamine platforms through an amide linkage and were synthesized by using microwave-assisted coupling reactions of carboxyl- or amine-substituted rosamines with the corresponding catechol units and subsequent deprotection. RosCat1 possesses a reverse amide, whereas RosCat2 has the usual oriented amide bond (HNCO vs. CONH, respectively). The ligands were characterized by means of NMR spectroscopy, mass-spectrometry, and DFT calculations and X-ray crystallography studies for RosCat1. The influence of the amide linkage on the photophysical properties of the fluorescent ligands was assessed in different solvents and showed a higher fluorescence quantum yield for RosCat1. The coordination chemistry of these ligands with a Fe-III center has been rationalized by mass-spectrometric analysis and semiempirical calculations. Octahedral Fe-III complexes were obtained by the chelation of three RosCat1 or RosCat2 ligands. Interestingly, the unconventional amide connectivity in RosCat1 imposes the formation of an eight-membered ring on the chelate complex through a salicylate-type mode of coordination.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 13