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Research Article

Chiral carbon dots from glucose by room temperature alkali-assisted synthesis for electrocatalytic oxidation of tryptophan enantiomers

Mengling Zhang1,2, Xing Fan3, Xin Du2, Yurong Ma2, Xiting Wang2, Hui Huang2, Yang Liu2, Youyong Li1,2( ), Zhenhui Kang1,2( )
Macao Institute of Materials Science and Engineering (MIMSE), MUST-SUDA Joint Research Center for Advanced Functional Materials, Macau University of Science and Technology, Taipa, Macao 999078, China
Institute of Functional Nano and Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-based Functional Materials and Devices, Joint International Research Laboratory of Carbon-Based Functional Materials and Devices, Soochow University, Suzhou 215123, China
Research Center for Carbon-based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871, China
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Graphical Abstract

Chiral carbon dots (LCDs and DCDs) were synthesized by base-catalyzed aldol reaction from chiral glucose. The obtained LCDs and DCDs have stereo-selective electrocatalytic activity toward tryptophan enantiomers (L-Trp and D-Trp), which is due to the different absorption (hydrogen bond interaction) of chiral CDs with the tryptophan enantiomers.

Abstract

Chiral catalysis is one of the most direct and effective approach to obtain pure optical enantiomers. Chiral carbon dots (CDs) as carbon-based chiral catalysts show great potential in chiral catalysis. Herein, we report a facile one step base-catalyzed aldol condensation to fabricate the chiral CDs from glucose at ambient temperature and pressure. The formation of chiral CDs involves the processes of isomerization and aldol condensation. These chiral CDs have been demonstrated that they have selective capacity for electrocatalytic oxidization of tryptophan enantiomers. L type of CDs (LCDs) is more likely to catalyze L-tryptophan (Trp) than D-Trp with the selective factor (IL/ID) of 1.60, whereas the D type of CDs (DCDs) tends to catalyze D-Trp (IL/ID: 0.63). Theoretical calculations combined with various contrast experiments (temperature and pH) demonstrate that the selectively electrocatalytic capacity of chiral CDs toward Trp isomers is due to the different hydrogen-bond interactions between chiral CDs and Trp.

Keywords

chiral carbon dotssynthesis mechanismelectrocatalysischiral catalysis

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Nano Research
Volume 16 Issue 7,
July 2023
Pages 8929-8936
DOI: 10.1007/s12274-023-5601-6
Cite this article:
Zhang M, Fan X, Du X, et al. Chiral carbon dots from glucose by room temperature alkali-assisted synthesis for electrocatalytic oxidation of tryptophan enantiomers. Nano Research, 2023, 16(7): 8929-8936. https://doi.org/10.1007/s12274-023-5601-6
Topics:
Carbon quantum dotsCatalyst selectivity ElectrocatalystsGraphene quantum dots

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Received: 18 January 2023
Revised: 08 February 2023
Accepted: 21 February 2023
Published: 18 April 2023
© Tsinghua University Press 2023
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