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    Achiral double-decker phthalocyanine assemble into helical nanofibers for electrochemically chiral recognition of tryptophan

    Year: 2021

    Journal: Colloid Surf. A-Physicochem. Eng. Asp., Volume 613, MAR 20

    Authors: Jiang, Yuying; Chen, Xin; Xiao, Zuoxu; Wang, Tianyu; Chen, Yanli

    Organizations: Natural Science Foundation of China [21631003, 21471015, 21671017, 21474118, 21773006]; Major Science and Technology Program for Water Pollution Control and Treatment [2017ZX07402001]; Beijing Municipal Commission of Education; University of Science and Technology Beijing [FRF-BR-16-008A]

    Keywords: Supramolecular chirality; Chiral recognition; Double-decker phthalocyanines; Interfacial assembly; Helical nanofibers

    Due to the unique role of homochirality in our life, efficiently sensing chiral biomolecules is essential for the health and well-being of people. However, electrochemically chiral recognition based on the assemblies of achiral building blocks was still rarely developed. Herein, depending on the co-assembly of achiral double-decker phthalocyanines (EuPc2-8) with poly-L-lysine at the air/water interface, discrimination enantiomers of tryptophan (Trp) even quantitatively can be achieved. The air/water interfacial assembly of achiral double-decker phthalocyanines (EuPc2-8) with poly-L-lysine forms long helical nanofibers with single-molecule-sized diameters, as well as optical activity. The nanostructures and different properties of EuPc2-8/poly-L-lysine helical nanofibers have been thoroughly characterized. The electrochemically chiral recognition of tryptophan is attributed to the unequal interactions between tryptophan enantiomers and EuPc2-8/poly-L-lysine co-assemblies, as verified by the calculated combination energy of EuPc2-8/poly-L-lysine with L- or D-Trp molecules. Therefore, the enrichment of L-Trp molecules rather than D-Trp molecules within EuPc2-8/poly-L-lysine assemblies can be achieved due to subtle features of double-decker phthalocyanines co-assemblies with supramolecular chirality, which results in electrochemically chiral discrimination. These results open new approach for developing efficient and low-cost electrochemically chiral sensor based on the assembly of achiral building blocks.
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