Fluorescent chemosensor for Ag(I) based on amplified fluorescence quenching of a new phthalocyanine bearing derivative of benzofuran

Abstract

A fluorescent chemosensor for Ag(I) as a new family of peripherally functionalized zinc-phthalocyanine, 2(3),9(10),16(17),23(24)-tetrakis-{6-(-benzofuran-2-carboxylate)-hexylthio} phthalocyaninatozinc(II) [Zn[Pc(beta-S(CH2)(6)OCOBz-furan)(4)], (ZnPcBzF). (3), which was derivated from 6-(3,4-dicyanophenylthio)-hexyl-2-benzofuranate (BzF), (2), has been synthesized and fully characterized by elemental analysis, FT-IR, H-1 and C-13 NMR, MS (ESI and Maldi-TOF). An optical silver ion (Ag(l)) sensor based on the fluorescence quenching of benzofuran moiety and ZnPc core was developed. Both absorbance and fluorescence spectra of ZnPcBzF, (3) exhibit distinct changes in visible region in response to treatment with Ag(l) ion in solution. Such properties make compound ZnPcBzF, (3) intriguing candidates for incorporation into the transducer layer in optically based chemical sensors. (C) 2009 Elsevier Ltd. All rights reserved.