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A New Chiral Binaphthalene‐Based Fluorescence Polymer Sensor for the Highly Enantioselective Recognition of Phenylalaninol
Author(s) -
Wei Guo,
Zhang Shuwei,
Dai Chunhui,
Quan Yiwu,
Cheng Yixiang,
Zhu Chengjian
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302726
Subject(s) - enantioselective synthesis , fluorescence , enantiomer , polymer , polymerization , benzaldehyde , naked eye , schiff base , chemistry , photochemistry , diamine , materials science , combinatorial chemistry , polymer chemistry , stereochemistry , organic chemistry , catalysis , optics , physics
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 NaBH 4 . 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.