Effects of single and double bonds in linkers on colorimetric and fluorescent sensing properties of polyving akohol grafting rhodamine hydrazides.

Abstract

Two rhodamine derivatives, N-mono-maleic acid amide-N'-rhodamine B hydrazide (MRBH) and N-mono-succinic acid amide-N'-rhodamine 6G hydrazide (SR6GH), were synthesized by amidation with maleic anhydride (MAH), succinic anhydride (SAH) and rhodamine B hydrazide, rhodamine 6G hydrazide, which were identified by FTIR, (1)H NMR and elemental analysis. Two water-soluble fluorescent materials (PVA-MRBH and PVA-SR6GH) were prepared via esterification reaction with N-mono-maleic acyl chloride amide-N'-rhodamine B hydrazide (MRBHCl) or N-mono-maleic acyl chloride amide-N'-rhodamine 6G hydrazide (SR6GHCl) and poly(vinyl alcohol) (PVA) in DMSO solution. The sensing behaviors of PVA-MRBH and PVA-SR6GH were explored by recording the fluorescence spectra in completely aqueous solution. Upon the addition of Cu(2+) and Fe(3+) ions to the aqueous solution of PVA-MRBH, visual color change from rose pink to amaranth and orange for Cu(2+) and Fe(3+) ions, respectively, and fluorescence quenching were observed. Titration of Cu(2+), Fe(3+), Cr(3+) or Hg(2+) into the aqueous solution of PVA-SR6GH, although they induced fluorescence enhancement, only Fe(3+) made the color changing from colorless to yellow. Moreover, other metal ions did not induce obvious changes to color and the fluorescence spectra.