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Synthesis and Chiral Recognition Properties of Novel Fluorescent Chemosensors for Amino Acid

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Abstract

The charge neutral chiral optical sensors 1a∼d containing thiourea and amide groups were synthesized by simple steps in good yields and their structures were characterized by IR, 1H NMR, 13C NMR, MS spectra and elemental analysis. The enantioselective recognition for α-phenylglycine and phenylglycinol was examined by fluorescence emission and UV-vis spectra. The fluorescence and UV-vis spectra changes of 1a were obvious when the enantiomers of α-phenylglycine anion were added, which exhibited that 1a has good enantioselective recognition ability towards α-phenylglycine.

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Acknowledgments

We thank the National Natural Science Foundation for financial support (Grant No. 20572080).

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Authors and Affiliations

  1. Department of Chemistry, Wuhan University, Wuhan, Hubei, 430072, People’s Republic of China

    Xiao-Huan Huang, Yong-Bing He, Chen-Guang Hu & Zhi-Hong Chen

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  1. Xiao-Huan Huang
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  2. Yong-Bing He
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  3. Chen-Guang Hu
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  4. Zhi-Hong Chen
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Correspondence to Yong-Bing He.

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Fig. S1

a Fluorescence spectra of receptor 1a (5 × 10−5 mol L−1) with l-Phol in DMSO. b Fluorescence spectra of receptor 1a (5 × 10−5 mol L−1) with d-Phol in DMSO. (DOC 126 kb)

Fig. S2

a Fluorescence spectra of receptor 1b (5 × 10−5 mol L−1) with l-Phol in DMSO. b Fluorescence spectra of receptor 1b (5 × 10−5 mol L−1) with d-Phol in DMSO. (DOC 147 kb)

Fig. S3

a Fluorescence spectra of receptor 1c (5 × 10−5 mol L−1) with l-Phe in DMSO. b Fluorescence spectra of receptor 1c (5 × 10−5 mol L−1) with d-Phe in DMSO. (DOC 106 kb)

Fig. S4

a Fluorescence spectra of receptor 1c (5×10−5 mol L−1) with l-Phol in DMSO. b Fluorescence spectra of receptor 1c (5 × 10−5 mol L−1) with d-Phol in DMSO. (DOC 124 kb)

Fig. S5

a Fluorescence spectra of receptor 1d (5 × 10−5 mol L−1) with l-Phe in DMSO. b Fluorescence spectra of receptor 1d (5 × 10−5 mol L−1) with d-Phe in DMSO. (DOC 112 kb)

Fig. S6

a UV–vis absorption spectra of receptor 1b (5 × 10−5 mol L−1) with l-Phe in DMSO. b UV–vis absorption spectra of receptor 1b (5 × 10−5 mol L−1) with d-Phe in DMSO. (DOC 70.5 kb)

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Huang, XH., He, YB., Hu, CG. et al. Synthesis and Chiral Recognition Properties of Novel Fluorescent Chemosensors for Amino Acid. J Fluoresc 19, 97–104 (2009). https://doi.org/10.1007/s10895-008-0385-3

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  • DOI: https://doi.org/10.1007/s10895-008-0385-3

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