title: A new chiral binaphthalene-based fluorescence polymer sensor for the highly enantioselective recognition of phenylalaninol.
abstract: A new (S)-binaphthalene-based polymer (P-1) was synthesized by the polymerization of 5,5'-((2,5-dibutoxy-1,4-phenylene)bis(ethyne-2,1-diyl))bis(2-hydroxy-3-(piperidin-1-ylmethyl) benzaldehyde (M-1) with (S)-2,2'-dimethoxy-(1,1'-binaphthalene)-3,3'-diamine (M-2) through the formation of a Schiff base; the corresponding chiral polymer (P-2) could be obtained by the reduction of polymer P-1 with NaBH4 . Chiral polymer P-1 exhibited a remarkable "turn-on" fluorescence-enhancement response towards (D)-phenylalaninol and excellent enantioselective recognition behavior with enantiomeric fluorescence difference ratios (ef) as high as 8.99. More importantly, chiral polymer P-1 displays a bright blue fluorescence color change upon the addition of (D)-phenylalaninol under a commercially available UV lamp, which can be clearly observed by the naked eye. On the contrary, chiral polymer P-2 showed weaker enantioselective fluorescence ability towards the enantiomers of phenylalaninol.
authors.affiliation: Key Lab of Mesoscopic Chemistry of MOE, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093 (P.R. China), Fax: (+86) 2583686508.
authors.forename: Guo
authors.initials: G
authors.lastname: Wei
authors.forename: Shuwei
authors.initials: S
authors.lastname: Zhang
authors.forename: Chunhui
authors.initials: C
authors.lastname: Dai
authors.forename: Yiwu
authors.initials: Y
authors.lastname: Quan
authors.forename: Yixiang
authors.initials: Y
authors.lastname: Cheng
authors.forename: Chengjian
authors.initials: C
authors.lastname: Zhu
mesh_terms: D009281:Naphthalenes / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000032:analysis; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet / Q000295:instrumentation*; D013237:Stereoisomerism
chemical_list: D009281:Naphthalenes; D011108:Polymers; D012545:Schiff Bases; C012481:phenylalaninol; C031721:naphthalene; D010649:Phenylalanine
keywords: binaphthalenes; enantioselectivity; molecular recognition; polymers; sensors