Polymer‐based fluorescence sensors incorporating chiral binaphthyl and benzo[2,1,3]thiadiazole moieties for Hg2+ detection

Abstract

AbstractThree chiral polymers P‐1, P‐2, and P‐3 could be obtained by the polymerization of (R)‐6,6′‐dibutyl‐3,3′‐diiodo‐2, 2′‐binaphthol (R‐M‐1), (R)‐6,6′‐dibutyl‐3,3′‐diiodo‐2,2′‐bisoctoxy‐1,1′‐binaphthyl (R‐M‐2), and (R)‐6,6′‐dibutyl‐3,3′‐diiodo‐2,2′‐bis (diethylaminoethoxy)‐1,1′‐binaphthyl (R‐M‐3) with 4,7‐diethynyl‐benzo[2,1,3]‐thiadiazole (M‐1) via Pd‐catalyzed Sonogashira reaction, respectively. P‐1, P‐2, and P‐3 can show pale red, blue–green, and orange fluorescence. The responsive optical properties of these polymers on various metal ions were investigated by fluorescence spectra. Compared with other cations, such as Co2+, Ni2+, Ag+, Cd2+, Cu2+, and Zn2+, Hg2+ can exhibit the most pronounced fluorescence response of these polymers. P‐1 and P‐2 show obvious fluorescence quenching effect upon addition of Hg2+, on the contrary, P‐3 shows fluorescence enhancement. Three polymer‐based fluorescent sensors also show excellent fluorescence response for Hg2+ detection without interference from other metal ions. The results indicate that these kinds of tunable chiral polybinaphthyls can be used as fluorescence sensors for Hg2+ detection. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 997–1006, 2010