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Perylene-functionalized graphene sheets modified with chitosan for voltammetric discrimination of tryptophan enantiomers

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Abstract

A composite was prepared from graphene functionalized with 3,4,9,10-perylene tetracarboxylic acid and chitosan (rGO-PTCA-chitosan) by a chemical method. It involves non-covalent functionalization of rGO with PTCA followed by amidation reaction with chitosan. Scanning electron microscopy, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy and electrochemical methods were used to characterize the composites. By combining the chiral features of chitosan and the excellent electrochemical behaviors of rGO-PTCA, a graphene-based material with enantioselectivity was constructed for electrochemical chiral recognition of tryptophan (Trp) enantiomers. A glassy carbon electrode (GCE) modified with rGO-PTCA-chitosan had a higher recognition capability for L-Trp than for D-Trp. Best operated at a working voltage near 0.78 V (vs. SCE), the enantioselectivity coefficient is 3.0. The sensor has a linear response in the 1 mM to 10 mM Trp concentration range and a 1.2 μM detection limit (at S/N = 3) for L-Trp, and of 3.0 μM to D-Trp. The sensor was successfully used to detect Trp enantiomers in real samples, and a recognition mechanism is presented.

Schematic presentation of a composoie prepared by graphene functionalized with 3,4,9,10-perylene tetracarboxylic acid and chitosan (rGO-PTCA-chitosan) via a chemical method. It involves non-covalent functionalization of rGO with PTCA followed by amidation reaction with chitosan and voltammetric determination of tryptophan enantiomers.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (51262027), the State Key Laboratory of Solidification Processing in NWPU (SKLSP201754), the Science and Technology Project Gansu Province (17YF1GA017), the Research Project of Higher Education in Gansu Province (2017A-002) and the Science and Technology Project Gansu Province (17JR5RA082).

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Authors and Affiliations

  1. Research Center of Gansu Military and Civilian Integration Advanced Structural Materials, Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, 730070, China

    Xing Yang, Xiaohui Niu, Zunli Mo, Ruibin Guo, Nijuan Liu, Pan Zhao & Zhenyu Liu

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  1. Xing Yang
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  2. Xiaohui Niu
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  3. Zunli Mo
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  4. Ruibin Guo
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  6. Pan Zhao
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Correspondence to Zunli Mo.

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Yang, X., Niu, X., Mo, Z. et al. Perylene-functionalized graphene sheets modified with chitosan for voltammetric discrimination of tryptophan enantiomers. Microchim Acta 186, 333 (2019). https://doi.org/10.1007/s00604-019-3442-5

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