Fluorescent molecular sensing of amino acids bearing an aromatic residue

被引：47

作者：

Fabbrizzi, L ^{[1
]}

Licchelli, M ^{[1
]}

Perotti, A ^{[1
]}

Poggi, A ^{[1
]}

Rabaioli, G ^{[1
]}

Sacchi, D ^{[1
]}

Taglietti, A ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Gen, I-27100 Pavia, Italy

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2001年 / Royal Society of Chemistry卷 / 11期

关键词：

D O I：

10.1039/b105480p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tetra-amino tripodal ligand, 3, containing two anthracene subunits, has been prepared through a multi-step synthesis and its solution properties have been studied by potentiometric and spectrofluorimetric techniques. The zine(II) complex, [Zn-II(3)](2+), which displays the typical emission of anthracene derivatives. interacts with natural amino acids, showing a particular affinity towards phenylalanine and tryptophan. This selective behaviour of the complex derives from its ability to establish two kinds of interaction: (i) a metal-ligand interaction between the zinc(ii) ion and the amino acid's carboxylate group; (ii) a pi -stacking interaction involving the aromatic moieties positioned on the complex and on the amino acid, inducing an extra stability of the adducts with tryptophan and phenylalanine (7-8 kJ mol(-1)). The formation of the 1 : 1 adduct with tryptophan is signalled by a strong fluorescence quenching while no effect on the emission intensity has been observed in all other cases.

引用

页码：2108 / 2113

页数：6

共 42 条

[1] A ditopic tetradentate pyridyl amine ligand containing an anthracene fragment:: fluorescence intensity and 'closed' vs.'open' species formation in the presence of Cu2+, as a function of pH [J].