Abstract

Chiral supramolecules have great potential for use in chiral recognition, sensing, and catalysis. Particularly, chiral supramolecular biocoordination polymers (SBCPs) provide a versatile platform for characterizing biorelated processes such as chirality transcription. Here, we selectively synthesize homochiral and heterochiral SBCPs, composed of chiral naphthalene diimide ligands and Zn ions, from enantiomeric and mixed R-ligands and S-ligands, respectively. Notably, we find that the chiral self-sorted SBCPs exhibit multifunctional properties, including photochromic, photoluminescent, photoconductive, and chemiresistive characteristics, thus can be used for various sensors. Specifically, these materials can be used for detecting hazardous amine materials due to the electron transfer from the amine to the SBCP surface and for enantioselectively sensing a chiral species naproxen due to the different binding energies with regard to their chirality. These results provide guidelines for the synthesis of chiral SBCPs and demonstrate their versatility and feasibility for use in various sensors covering photoactive, chemiresistive, and chiral sensors.

Highlights

  • Chiral supramolecules have great potential for use in chiral recognition, sensing, and catalysis

  • H2AlaNDI homochiral ligands were synthesized from 1,4,5,8-naphthalenetetracarboxylic dianhydride (NTCDA) and L-alanine or D-alanine, which were refluxed for 12 h in pyridine[31], and a NDI ligand with alanine termini (AlaNDI)-Zn supramolecular biocoordination polymers (SBCPs) were synthesized using a solvothermal reaction between the ligands and zinc iodide in N,N-dimethylformamide (DMF) in a sealed stainless-steel tube with a Teflon liner at 120 °C for 72 h with yields of 29, 27, and 21% for (S)-AlaNDI-Zn, (R)-AlaNDIZn, and (Rac)-AlaNDI-Zn, respectively

  • Single-crystal X-ray diffraction (XRD) analysis revealed that (S)-AlaNDI-Zn and (R)-AlaNDI-Zn crystallize as a monoclinic P21 space group from pure enantiomers

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Summary

Introduction

Chiral supramolecules have great potential for use in chiral recognition, sensing, and catalysis. Unlike the common strategies for photoswitchable CPs that use reversible structural or geometrical changes of the ligand upon light irradiation[28], the developed AlaNDI-Zn SBCPs include photochromic and redox ligand NDI, which can be reversibly converted between a radical state and a neutral state by turning the light on and off, respectively.

Results
Conclusion

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