A New Chiral Binaphthalene‐Based Fluorescence Polymer Sensor for the Highly Enantioselective Recognition of Phenylalaninol |
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| Authors: | Guo Wei Shuwei Zhang Chunhui Dai Yiwu Quan Prof Dr Yixiang Cheng Prof Dr Chengjian Zhu |
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| Institution: | 1. Key Lab of Mesoscopic Chemistry of MOE, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093 (P.R. China), Fax: (+86)?2583686508;2. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093 (P.R. China), Fax: (+86)?2583686508 |
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| 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. |
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| Keywords: | binaphthalenes enantioselectivity molecular recognition polymers sensors |
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