The synthesis of new calix[6]arene derivatives bearing anthracenyl and naphthyl fluorescent units at the lower rim is here reported. The threading abilities of these new derivatives toward dialkylammonium and bis(benzylalkylammonium) axles were investigated by NMR and fluorescence spectroscopy. A quenching of the fluorescence of the calix-wheels was observed upon threading with ammonium axles. Finally, DFT calculations evidenced that stabilizing C–H···π interactions are present between the axle and the anthracenyl or naphthyl group of the wheel, in addition to the usual H-bond interactions between the ammonium group of the axle and the oxygen atoms of the calix-wheel.
Threading fluorescent calixarene-wheels with ammonium axles
Talotta, Carmen
;Caruso, Tonino;De Rosa, Margherita
;Gaeta, Carmine;Soriente, Annunziata;Neri, Placido
2018
Abstract
The synthesis of new calix[6]arene derivatives bearing anthracenyl and naphthyl fluorescent units at the lower rim is here reported. The threading abilities of these new derivatives toward dialkylammonium and bis(benzylalkylammonium) axles were investigated by NMR and fluorescence spectroscopy. A quenching of the fluorescence of the calix-wheels was observed upon threading with ammonium axles. Finally, DFT calculations evidenced that stabilizing C–H···π interactions are present between the axle and the anthracenyl or naphthyl group of the wheel, in addition to the usual H-bond interactions between the ammonium group of the axle and the oxygen atoms of the calix-wheel.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
