Salen-Based Chiral Fluorescence Polymer Sensor for Enantioselective Recognition of 伪-Hydroxyl Carboxylic Acids

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• 作者：Fengyan Song ; Guo Wei ; Lu Wang ; Jiemin Jiao ; Yixiang Cheng ; Chengjian Zhu
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：May 18, 2012
• 年：2012
• 卷：77
• 期：10
• 页码：4759-4764
• 全文大小：383K
• 年卷期：v.77,no.10(May 18, 2012)
• ISSN：1520-6904

文摘

(R,R)-Salen-based chiral polymer P-1 was synthesized by the polymerization of 5,5鈥?((2,5-dibutoxy-1,4-phenylene)bis(ethyne-2,1-diyl))bis(2-hydroxy-3-(piperidin-1-ylmethyl) benzaldehyde (M-1) with (1R,2R)-cyclohexane-1,2-diamine (M-2) via nucleophilic addition鈥?elimination reaction, and (R,R)-salan-based polymer P-2 could be obtained by the reduction reaction of P-1 with NaBH₄. (R,R)-Salen-based chiral polymer P-1 can exhibit greater fluorescence enhancement response toward (l)-伪-hydroxyl carboxylic acids, and the value of enantiomeric fluorescence difference ratio (ef) can reach as high as 8.41 for mandelic acid and 6.55 for lactic acid. On the contrary, (R,R)-salan-based chiral polymer P-2 shows obvious fluorescence quenching response toward 伪-hydroxyl carboxylic acids. Most importantly, (R,R)-salen-based polymer P-1 can display bright blue fluorescence color change in the presence of (l)-伪-hydroxyl carboxylic acids under a commercially available UV lamp, which can be clearly observed by the naked eyes.