In Situ Generated 1:1 Zn(II)-Containing Polymer Complex Sensor for Highly Enantioselective Recognition of N-Boc-Protected Alanine

A novel chiral ( S )-BINAM-based fluorescence polymer sensor was designed and synthesized by the polymerization of 5,5′-((2,5-dioctyloxy-1,4-phenylene)bis(ethyne-2,1-diyl)bis(2-hydroxy-3-(piperidin-1-ylmethyl)benzaldehyde ( M-1 ) with ( S )-2,2′-binaphthyldiamine ( S - BINAM, M-2 ) via Schiff’s base formation. The resulting chiral polymer sensor shows very weak fluorescence but exhibits the obvious fluorescence enhancement response toward Zn 2+ . The in situ generated 1:1 Zn(II)-containing complex of chiral polymer can serve as a fluorescence sensor for highly enantioselective recognition of N-Boc-protected alanine, and the value of enantiomeric fluorescence difference ratio ( ef ) can reach as high as 6.90. This is the first report on the in situ generated chiral polymer complex used as a fluorescence sensor for highly enantioselective recognition of N-Boc-protected alanine.