Skip to main content
Log in

Hairpin-like structure and Jahn–Teller distortions in adenosine monophosphate copper coordination polymers: synthesis and chirality

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

Nucleotides are fundamental units that make up nucleic acids and can be utilized to create functional materials with specific structures. The Jahn–Teller distortions provide information about the orientation of ligands that are coordinated with copper(II) in coordination materials. Herein, we are going to report two coordination polymers [Cu(AMP)(bpe)(H2O)3]·11H2O (1) and [Cu(AMP)(bpe)(H2O)3]·8H2O constructed by combining bipyridyl ethylene (bpe), adenosine monophosphate (AMP), and copper(II) ions, which were analyzed using single-crystal X-ray diffraction, FTIR, TGA, and chiral dichroism spectroscopy. The coordination polymers were examined to study their structural details related to hairpin-like structure and Jahn–Teller distortions. It was observed that the AMP’s chirality, or the way it twists, is maintained when AMP is combined with copper through noncovalent interactions. Our results indicate that the chirality of AMP with copper can be well preserved and delivered to its supramolecular architecture through noncovalent interactions. This research work sheds light on the self-assembly of purine nucleotide hairpins in coordination polymers and their characterization. To the best of our knowledge, Jahn–Teller distortion and hairpin-like structures in nucleotide coordination polymers have been discussed rarely. Nucleotide coordination polymers can be used for potential applications in the fields such as fluorescent detection, medicine, artificial data storage, and energy devices.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  • Abdelaal A et al (2023) Data-driven framework for real-time rheological properties prediction of flat rheology synthetic oil-based drilling fluids. ACS omega

  • Alkhamis K et al (2023) Synthesis and investigation of bivalent thiosemicarbazone complexes: conformational analysis, methyl green DNA binding and in-silico studies. Arab J Sci Eng 48(1):273–290

    Article  CAS  Google Scholar 

  • Al-Wasidi AS et al (2023) Functionalization of silica nanoparticles by 5-chloro-8-quinolinol as a new nanocomposite for the efficient removal and preconcentration of Al3+ ions from water samples. ACS omega

  • Armentano D et al (2007) A new octanuclear copper(II)− nucleoside wheel. J Am Chem Soci 129(10):2740–2741

    Article  CAS  Google Scholar 

  • Berardan D et al (2017) Controlled Jahn-Teller distortion in (MgCoNiCuZn) O-based high entropy oxides. J Alloys Compd 704:693–700

    Article  CAS  Google Scholar 

  • Bruno R et al (2017) Cytosine nucleobase ligand: a suitable choice for modulating magnetic anisotropy in tetrahedrally coordinated mononuclear CoII compounds. Inorg Chem 56(4):1857–1864

    Article  CAS  PubMed  Google Scholar 

  • Conradie J (2019) Jahn-Teller effect in high spin d4 and d9 octahedral metal-complexes. Inorganica Chim Acta 486:193–199

    Article  CAS  Google Scholar 

  • Fleming AM, Burrows C (2019) Interplay of guanine oxidation and G-quadruplex folding in gene promoters. J Am Chem Soc 142:1115–1136

    Article  Google Scholar 

  • Freitag R, Conradie J (2013) Understanding the Jahn-Teller effect in octahedral transition-metal complexes: a molecular orbital view of the Mn (β-diketonato) 3 complex. J Chem Edu 90(12):1692–1696

    Article  CAS  Google Scholar 

  • Georgopoulou AN et al (2017) Dynamic versus static character of the magnetic Jahn-Teller effect: magnetostructural studies of [Fe3O (O2CPh) 6 (Py) 3] ClO4· py. Inorg Chem 56(2):762–772

    Article  CAS  PubMed  Google Scholar 

  • Gui D et al (2018) Jahn-Teller effect on framework flexibility of hybrid organic–inorganic perovskites. J Phys Chem 9(4):751–755

    CAS  Google Scholar 

  • Halcrow M (2013) Jahn-Teller distortions in transition metal compounds, and their importance in functional molecular and inorganic materials. Chem Soc Rev 42(4):1784–1795

    Article  CAS  PubMed  Google Scholar 

  • Imaz I et al (2011) Metal–biomolecule frameworks (MBioFs). ChemComm 47(26):7287–7302

    CAS  Google Scholar 

  • Iqbal MJ et al (2021a) Studies on the structure and chirality of A-motif in adenosine monophosphate nucleotide metal coordination complexes. CrystEngComm 23(23):4175–4180

    Article  CAS  Google Scholar 

  • Iqbal MJ et al (2021b) PH controlled the supramolecular assemblies of two guanosine monophosphate cadmium metal coordination complexes: structure and chirality. https://doi.org/10.21203/rs.3.rs-968925/v1

  • Joyce G, Szostak J (2018) Protocells and RNA self-replication. Cold Spring Harb 10(9):a034801

    Article  Google Scholar 

  • Livshits M et al (2020) Trifluoromethylated phenanthroline ligands reduce excited-state distortion in homoleptic copper (I) complexes. Inorg Chem 59(5):2781–2790

    Article  CAS  PubMed  Google Scholar 

  • Long S et al (2020) Jahn-Teller driven electronic instability in thermoelectric tetrahedrite. Adv Funct Mater 30(12):1909409

    Article  CAS  Google Scholar 

  • Martins L et al (2020) Evaluating the performance of a non-bonded Cu2+ model including Jahn−Teller effect into the binding of tyrosinase inhibitors. Int J Mol Sci 21(13):4783

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mogharbel A et al (2023) Green synthesis and characterization of new carbothioamide complexes; cyclic voltammetry and DNA/methyl green assay supported by silico ways versus DNA-polymerase. Arab J Chem 16(7):104807

    Article  CAS  Google Scholar 

  • Mohanty S, Mukherjee S (2022) Effect of Jahn-Teller distortion on microstructural and dielectric properties of La based double perovskites. J Alloys Compd 892:162204

    Article  CAS  Google Scholar 

  • Ouyang F et al (2021) Synthesis, structures and magnetic properties of copper(II) complexes with 1, 2, 3-triazole derivate as ligand: a single-crystal-to-single-crystal transformation from mononuclear to polymeric complex of copper(II). Transit Met Chem 46:315–322

    Article  CAS  Google Scholar 

  • Pu F et al (2018) Nucleobases, nucleosides, and nucleotides: versatile biomolecules for generating functional nanomaterials. Chem Soc Rev 47(4):1285–1306

    Article  CAS  PubMed  Google Scholar 

  • Qiu Q et al (2017) Cytosine-cytosine base-pair mismatch and chirality in nucleotide supramolecular coordination complexes. Eur Chem 23(30):7201–7206

    Article  CAS  Google Scholar 

  • Rák Z et al (2018) Evidence for Jahn-Teller compression in the (Mg Co, Ni, Cu, Zn) O entropy-stabilized oxide: a DFT study. Mater Lett 217:300–303

    Article  Google Scholar 

  • Sahoo J et al (2016) Coordinatively unsaturated lanthanide (III) helicates: luminescence sensors for adenosine monophosphate in aqueous media. Angew Chem Int Ed 55(33):9625–9629

    Article  CAS  Google Scholar 

  • Sanchez-Movellan I et al (2020) Local structure and excitations in systems with CuF 6 4 units: lack of Jahn-Teller effect in the low symmetry compound Na2CuF4. Phys Chem Phys 22(15):7875–7887

    Article  CAS  Google Scholar 

  • Song W et al (2021) Controllable synthesis of two adenosine 5′-monophosphate nucleotide coordination polymers via pH regulation: crystal structure and chirality. Dalton Trans 50(13):4713–4719

    Article  CAS  PubMed  Google Scholar 

  • Sui H et al (2019) siRNA containing a unique 5-nucleotide motif acts as a quencher of IFI16-mediated innate immune response. Mol Immunol 114:330–340

    Article  CAS  PubMed  Google Scholar 

  • Sukhikh A et al (2018) Jahn-teller effect in the [CuEn3] CrO4 structure. J Struct Chem 59(3):657–663

    Article  CAS  Google Scholar 

  • Takaeva M et al (2021) Preparation of solutions of copper and nickel en and dien complexes-an illustration of the Jahn-Teller effect. J Phys Conf Ser 1889:022072

    Article  CAS  Google Scholar 

  • Xu L et al (2018) Continuously tunable nucleotide/lanthanide coordination nanoparticles for DNA adsorption and sensing. ACS Omega 3(8):9043–9051

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhou P, Hui L (2011) Chirality delivery from a chiral copper(II) nucleotide complex molecule to its supramolecular architecture. Dalton Trans 40(18):4834–4837

    Article  CAS  PubMed  Google Scholar 

  • Zhou P et al (2015) Supramolecular self-assembly of nucleotide–metal coordination complexes: from simple molecules to nanomaterials. Coord Chem Rev 292:107–143

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China. I acknowledge that Rizwan Shoukat performed this work in the framework of the international Ph.D. in Innovation Sciences and technologies at the Università degli Studi di Cagliari, Italy.

Author information

Authors and Affiliations

Authors

Contributions

All authors are contributed to this work.

Corresponding authors

Correspondence to Muhammad Javed Iqbal or Hui Li.

Ethics declarations

Conflict of interest

There is no competing interest in this work.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 7420 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Iqbal, M.J., Shoukat, R., Talha, K. et al. Hairpin-like structure and Jahn–Teller distortions in adenosine monophosphate copper coordination polymers: synthesis and chirality. Chem. Pap. 77, 5687–5699 (2023). https://doi.org/10.1007/s11696-023-02888-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-023-02888-z

Keywords

Navigation