Fluorescent chemosensor for metal ions based on optically active polybinaphthyls and 1,3,4-oxadiazole

Linear chiral polymers P-1 and P-2 were synthesized by the polymerization of (R)-5,5'-dibromo-6,6'-di(4-methylphenyl)-2,2'-bisoctoxy1,1'-binaphthyl (R-M-1) with 2,5-di(4-vinylphenyl)-1,3,4-oxadiazole (M-2) and 2,5-di(4-tributylstannylphenyl)-1,3,4-oxadiazole (M-3) via Heck and Stille cross-coupling reaction, respectively. The chiral conjugated polymer P-1 can show strong green-blue fluorescence, and the chiral polymer P-2 shows strong blue fluorescence. While the conjugated polymers P-1 and P-2 were used as fluorescent chemosensor for metal ions, their fluorescence can be efficiently quenched on the addition of different metal ions. The obvious quenching effect of the polymers P-1 and P-2 indicates that the intramolecular photoinduced electron transfer (PET) or photoinduced charge transfer (PCT) between the polymer backbone and receptor-ions in the main chain of fluorescent chemosensor can lead to the pronounced fluorescence quenching. The results also show that the chiral polymers P-1 and P-2 incorporating 1,3,4-oxadiazole moiety as the recognition site can act as a special fluorescent chemosensor for the appropriate detection of the sensitive and selective sense of metal ions. (c) 2007 Elsevier Ltd. All rights reserved.