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<p>Two chiral covalent organic polymers (R)-COP and (S)-COP, respectively, were synthesized by Schiff base reaction using tri(4-formyl phenoxy)cyanurate (TFPC) and (1R,2R)-( +)-1,2-Diphenyl-1,2-ethanediamine or (1S,2S)-( +)-1,2-Diphenyl-1,2-ethanediamine as the building blocks. Electrochemical sensors (R)-COP/GCE and (S)-COP/GCE were prepared by coating the two chiral COPs on the surface of glassy carbon electrode (GCE) to detect tryptophan enantiomers. The results showed that both (R)-COP/GCE and (S)-COP/GCE could effectively recognize L-tryptophan (L-Trp) and D-tryptophan (D-Trp). The experimental results indicate that heterochiral interaction had an advantage over homogeneous ones between D-(or L-)Trp and R-(or S-)COP/GCE. Moreover, it was found that there is higher recognition efficiency for tryptophan on (R)-COP/GCE than on (S)-COP/GCE. The obtained (R)-COP/GCE and (S)-COP/GCE electrodes were also used for the determination of tryptophan enantiomer excess (ee), and a good linear relationships were found between the peak current and ee% of tryptophan for both (R)-COP/GCE and (S)-COP/GCE electrodes. Through the optimization of experimental conditions, it is found that there is a good linear relationship between the D-tryptophan concentration on (R)-COP/GCE electrode and the oxidation current in the concentration range of 1 ~ 50 µM and 50 ~ 300 µM D-tryptophan. The detection limit of D-tryptophan was 0.1 µM on (R)-COP/GCE.</p>

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Electrochemical enantioselective sensor for effective recognition of tryptophan isomers based on novel chiral triazinyl covalent organic polymer

  • 期刊论文

  • 发表日期：

    2025年4月29日

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  • Zhili Fang,
  • Xiaoguang Li,
  • Ying Nie,
  • Hui Zhang,
  • Wenyuan Xu,
  • Qixiang Nie

摘要

Two chiral covalent organic polymers (R)-COP and (S)-COP, respectively, were synthesized by Schiff base reaction using tri(4-formyl phenoxy)cyanurate (TFPC) and (1R,2R)-( +)-1,2-Diphenyl-1,2-ethanediamine or (1S,2S)-( +)-1,2-Diphenyl-1,2-ethanediamine as the building blocks. Electrochemical sensors (R)-COP/GCE and (S)-COP/GCE were prepared by coating the two chiral COPs on the surface of glassy carbon electrode (GCE) to detect tryptophan enantiomers. The results showed that both (R)-COP/GCE and (S)-COP/GCE could effectively recognize L-tryptophan (L-Trp) and D-tryptophan (D-Trp). The experimental results indicate that heterochiral interaction had an advantage over homogeneous ones between D-(or L-)Trp and R-(or S-)COP/GCE. Moreover, it was found that there is higher recognition efficiency for tryptophan on (R)-COP/GCE than on (S)-COP/GCE. The obtained (R)-COP/GCE and (S)-COP/GCE electrodes were also used for the determination of tryptophan enantiomer excess (ee), and a good linear relationships were found between the peak current and ee% of tryptophan for both (R)-COP/GCE and (S)-COP/GCE electrodes. Through the optimization of experimental conditions, it is found that there is a good linear relationship between the D-tryptophan concentration on (R)-COP/GCE electrode and the oxidation current in the concentration range of 1 ~ 50 µM and 50 ~ 300 µM D-tryptophan. The detection limit of D-tryptophan was 0.1 µM on (R)-COP/GCE.