A New Chiral Binaphthalene‐Based Fluorescence Polymer Sensor for the Highly Enantioselective Recognition of Phenylalaninol. Issue 47 (10th October 2013)

• Record Type: Journal Article
• Authors: Wei, Guo; Zhang, Shuwei; Dai, Chunhui; Quan, Yiwu; Cheng, Yixiang; Zhu, Chengjian
• Is Part Of: Chemistry. Volume 19:Issue 47(2013)
• Page Start: 16066
• Page End: 16071
• Publication Date: 2013-10-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201302726
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new (<italic>S</italic>)‐binaphthalene‐based polymer (<bold>P</bold>‐<bold>1</bold>) 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 (<bold>M</bold>‐<bold>1</bold>) with (<italic>S</italic>)‐2, 2′‐dimethoxy‐(1, 1′‐binaphthalene)‐3, 3′‐diamine (<bold>M</bold>‐<bold>2</bold>) through the formation of a Schiff base; the corresponding chiral polymer (<bold>P</bold>‐<bold>2</bold>) could be obtained by the reduction of polymer <bold>P</bold>‐<bold>1</bold> with NaBH₄. Chiral polymer <bold>P</bold>‐<bold>1</bold> exhibited a remarkable "turn‐on" fluorescence‐enhancement response towards (<sc>D</sc>)‐phenylalaninol and excellent enantioselective recognition behavior with enantiomeric fluorescence difference ratios (<italic>ef</italic>) as high as 8.99. More importantly, chiral polymer <bold>P</bold>‐<bold>1</bold> displays a bright blue fluorescence color change upon the addition of (<sc>D</sc>)‐phenylalaninol under a commercially available UV lamp, which can be clearly observed by the naked eye. On the contrary, chiral polymer <bold>P</bold>‐<bold>2</bold> showed weaker enantioselective fluorescence ability towards the enantiomers of phenylalaninol.</p> </abstract>