A chiral polymer‐based turn‐on fluorescent sensor for specific recognition of hydrogen sulfate

Abstract

Abstract A new kind of polymeric chemosensor containing chiral naphthaldimine moiety in the side chain was synthesized by the reversible addition‐fragmentation chain transfer polymerization of N ‐{[2‐(4‐vinylbenzyloxy)‐1‐naphthyl]‐methylene}‐( S )‐2‐phenylglycinol (VNP). The resulting polymers (PVNP) showed high selectivity for hydrogen sulfate relative to other anions including F − , Cl − , Br − , H 2 PO , CH 3 CO , and NO in tetrahydrofuran (THF) solution as judged from UV−vis, fluorescence, and circular dichroism spectrophotometric titrations. Compared with its monomer, the polymer has proven to be more attractive for detection of HSO in terms of sensitivity and reproducibility. Upon addition of the anion it gives remarkable spectral responses concomitant with detectable color change from colorless to pale yellow. Furthermore, the HSO ‐induced CD or fluorescence signal can be totally reversed with addition of base and eventually recovered the initial state, leading to a reproducible molecular switch with two distinguished “on” and “off” states. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012