title: Hg(2+) -induced in situ generated radical cation of (S)-BINOL-based polymer for highly enantioselective recognition of phenylalaninol.
abstract: Phenylalaninol enantiomers are one of the most important chiral compounds due to its presence in biologically active molecules and pharmaceutical products. In this paper, a novel chiral fluorescence polymer sensor incorporating (S)-BINOL and oligomeric aniline via a nucleophilic addition-elimination reaction is designed and synthesized. Polymer sensor exhibits "turn-off" fluorescence quenching response upon the addition of Hg(2+) , and "turn-on" moderate fluorescence enhancement behavior towards phenylalaninol enantiomers. Meanwhile, this kind of (S)-BINOL-based polymer sensor can exhibit highly selective enantioselective recognition response towards (L)-phenylalaninol upon the addition of Hg(2+) and the value of ef can reach as high as 5.4, which can be attributed to the formation of in situ generated radical cation arisen from oligomeric aniline moiety by Hg(2+) induction.
authors.affiliation: Key Laboratory of Mesoscropic Chemistry of MOE, School of Chemistry and Chemical Engineering, Nanjing University, No. 22, Hankou Road, Nanjing, 210093, China.
authors.forename: Jiemin
authors.initials: J
authors.lastname: Jiao
authors.forename: Fei
authors.initials: F
authors.lastname: Li
authors.forename: Shuwei
authors.initials: S
authors.lastname: Zhang
authors.forename: Yiwu
authors.initials: Y
authors.lastname: Quan
authors.forename: Wenhua
authors.initials: W
authors.lastname: Zheng
authors.forename: Yixiang
authors.initials: Y
authors.lastname: Cheng
authors.forename: Chengjian
authors.initials: C
authors.lastname: Zhu
mesh_terms: D002412:Cations / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D008628:Mercury / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000032:analysis; D011108:Polymers / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism
chemical_list: C406944:BINOL, naphthol; D002412:Cations; D005456:Fluorescent Dyes; D009284:Naphthols; D011108:Polymers; C012481:phenylalaninol; D010649:Phenylalanine; D008628:Mercury
keywords: enantioselectivity; fluorescence probe; molecular recognition; polymer; radical ions