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Citation: BAI Lei, HUO Shu-Hui, HAN Zhen-Gang, CHEN Jing. Bifunctional Squaramide Fluorescent Probes for Chiral Recognition[J]. Chinese Journal of Analytical Chemistry, ;2019, 47(8): 1219-1226. doi: 10.19756/j.issn.0253-3820.191056 shu

Bifunctional Squaramide Fluorescent Probes for Chiral Recognition

College of Chemistry and Chemical Engineering, Northwest Normal University, Key Laboratory of Bioelectrochemistry & Environmental Analysis of Gansu Province, Lanzhou 730070, China

Received Date: 26 January 2019
Revised Date: 28 May 2019

Fund Project: This work was supported by the National Natural Science Foundation of China (No. 21462036), the Natural Science Foundation of Gansu Province, China(Nos. 18JR3RA085, 145RJYA239) and the Research Projects for the Gansu Universities (No. 2015A-027).

Four chiral bifunctional squaramide fluorescent probes were synthesized, including new compounds 1 and 3, and known compounds 2 and 4, and their structure were confirmed by ¹H NMR, ¹³C NMR and HRMS spectra. The fluorescence chiral recognition effects of these four probes on Boc-phenylalanine, phenylalanine, phenylglycine, proline, valine, tartaric acid, mandelic acid, and binaphthol were systematically investigated by fluorescence spectroscopy. By combinatorial screening, it was found that the probe 4 had good recognition effect on valine. Further research showed that the fluorescence peak showed a sharp blue shift and the fluorescence intensity was greatly reduced after addition of L-valine at 1:2 molar ratio of probe 4 to valine. By contrast, there was no obvious change on the fluorescence intensity after addition of D-valine, and the fluorescence intensity ratio (I_D/I_L) value was up to 1.35. Based on this, a two-chiral-centers recognition mechanism was proposed. The tertiary amine and squaramide group of the probe 4 separately combined with one molecule of L-valine by electrostatic and hydrogen bonding interactions.
- Chiral recognition,
- Fluorescence probe,
- Squaramide,
- Bifunctional,
- Non-derivative amino acid
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