Skip to main content
SpringerLink
Log in

Anion binding properties for pyrophosphate derived from a 2,6-diamidopyridinedipyrromethane macrocycle

  • Short Communication
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

A 2,6-diamidopyridinedipyrromethane macrocyclic receptor was prepared by a Schiff base condensation reaction. The structures of the free macrocycle and its complex with H2P2O72− were analyzed by single crystal X-ray diffraction (SC-XRD). The stability constants for the binding of the receptor with tetrabutylammonium salts of HP2O73− were determined by isothermal titration calorimetry using acetonitrile solutions. According to the titration data, the receptor exhibited high affinity with HP2O73−. The crystal structure analysis demonstrated that the neutral sandwich-type pyrophosphate complex was formed via the protonation of the macrocyclic receptor.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

References

  • Aldakov D, Palacios MA, Anzenbacher P Jr (2005) Benzothiadiazoles and dipyrrolyl quinoxalines with extended conjugated chromophores-fluorophores and anion sensors. Chem Mater 17:5238–5241

    Article  CAS  Google Scholar 

  • Anzenbacher P Jr, Jursíková K, Sessler JL (2000) Second generation calixpyrrole anion sensors. J Am Chem Soc 122:9350–9351

    Article  CAS  Google Scholar 

  • Busschaert N, Caltagirone C, Rossom WV, Gale PA (2015) Applications of supramolecular anion recognition. Chem Rev 115:8038–8155

    Article  CAS  Google Scholar 

  • Ghosh K, Sarkar AR, Samadder A, Khuda-Bukhsh AR (2012) Pyridinium-based fluororeceptors as practical chemosensors for hydrogen pyrophosphate (HP2O73-) in semiaqueous and aqueous environments. Org Lett 14(17):4314–4317

    Article  CAS  Google Scholar 

  • Gonzáez L, Zapata F, Caballero A, Molina P, Arellano CRD, Alkorta I, Elguero J (2016) Host-guest chemistry: oxoanion recognition based on combined charge-assisted C-H or halogen-bonding interactions and anion·anion interactions mediated by hydrogen bonds. Chem Eur J 22:7533–7544

    Article  Google Scholar 

  • He Q, Kelliher M, Bähring S, Lynch VM, Sesser JL (2017) A Bis-calix[4]pyrrole enzyme mimic that constrains two oxoanions in close proximity. J Am Chem Soc 139:7140–7143

    Article  CAS  Google Scholar 

  • Hossain MA, Llinares JM, Powell D, James KB (2001) Multiple hydrogen bond stabilization of a sandwich complex of sulfate between two macrocyclic tetraamides. Inorg Chem 40:2936–2937

    Article  CAS  Google Scholar 

  • Ji L, Yang Z, Zhao Y, Sun M, Cao L, Yang XJ, Wang YY, Wu B (2016) Sandwich phosphate complexes of macrocyclic tris(urea) ligands and their rotation around the anion. Chem Comm 52:7310–7313

    Article  CAS  Google Scholar 

  • Katsiaouni S, Dechert S, Briñas RP, Brückner C, Meyer F (2008) Schiff base macrocycles containing pyrroles and pyrazoles. Chem Eur J 14:4823–4835

    Article  CAS  Google Scholar 

  • Kim SK, Singh NJ, Kwon J, Hwang IC, Park SJ, Kim KS, Yoon J (2006) Fluorescent imidazolium receptors for the recognition of pyrophosphate. Tetrahedron 62:6065–6072

    Article  CAS  Google Scholar 

  • Kubik S (2017) Anion recognition in aqueous media by cyclopeptides and other synthetic receptors. Acc Chem Res 50:2870–2878

    Article  CAS  Google Scholar 

  • Li Y, Pink M, Karty JA, Flood AH (2008) Dipole-promoted and size-dependent cooperativity between pyridyl-containing triazolophanes and halides leads to persistent sandwich complexes with iodide. J Am Chem Soc 130:17293–17295

    Article  CAS  Google Scholar 

  • Mahanta SP, Kumar BS, Baskaran S, Sivasankar C, Panda PK (2012) Colorimetric sensing of fluoride ion by new expanded Calix[4]pyrrole through anion-π interaction. Org Lett 14(2):548–551

    Article  CAS  Google Scholar 

  • Mungalpara D, Valkonen A, Rissanen K, Kubik S (2017) Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties. Chem Sci 8:6005–6013

    Article  CAS  Google Scholar 

  • Nishizawa S, Kato Y, Teramae N (1999) Fluorescence sensing of anions via intramolecular excimer formation in a pyrophosphate-induced self-assembly of a pyrene-functionalized guanidinium receptor. J Am Chem Soc 121:9463–9464

    Article  CAS  Google Scholar 

  • Özkar S, Ülkü D, Yıldrım LT, Biricik N, Gümgüm BJ (2004) Crystal and molecular structure of bis(acetylacetone)ethylenediimine: intramolecular ionic hydrogen bonding in solid state. Mol Struct 688:207–211

    Article  Google Scholar 

  • Ronaghi M, Karamohamed S, Petterson B, Uhlén M, Nyrén P (1996) Real-time DNA sequencing using detection of pyrophosphate release. Anal Biochem 242:84–89

    Article  CAS  Google Scholar 

  • Sessler JL, Katayev E, Pantos GD, Ustynyuk YA (2004) Synthesis and study of a new diamidodipyrromethane macrocycle. An anion receptor with a high sulfate-to-nitrate binding selectivity. Chem Commun 11:1276–1277

    Article  Google Scholar 

  • Sessler JL, Katayev E, Pantos GD, Scherbakov P, Reshetova MD, Khrustalev VN, Lynch VM, Ustynyuk YA (2005) Fine tuning the anion binding properties of 2,6-Diamidopyridine dipyrromethane hybrid macrocycles. J Am Chem Soc 127:11442–11446

    Article  CAS  Google Scholar 

  • Sessler JL, Gross DE, Cho WS, Lynch VM, Schmidtchen FP, Bates GW, Light ME, Gale PA (2006) Calix[4]pyrrole as a chloride anion receptor: solvent and countercation effects. J Am Chem Soc 128:12281–12288

    Article  CAS  Google Scholar 

  • Sessler JL, Cai J, Gong HY, Yang X, Arambula JF, Hay BP (2010) A pyrrolyl-based triazolophane: a macrocyclic receptor with CH and nh donor groups that exhibits a preference for pyrophosphate anions. J Am Chem Soc 132(40):14058–14060

    Article  CAS  Google Scholar 

  • Thordarson P (2011) Determining association constants from titration experiments in supramolecular chemistry. Chem Soc Rev 40:1305–1323

    Article  CAS  Google Scholar 

  • Xu S, He M, Yu H, Cai X, Tan X, Lu B, Shu B (2001) A Quantitative method to measure telomerase activity by bioluminescence connected with telomeric repeat amplification protocol. Anal Biochem 299:188–193

    Article  CAS  Google Scholar 

  • Yu X, Clegg JK, Zhang YQ, Xue SF, Tao Z, Zhu QJ, Lindoy LF, Wei G (2015) Adducts of aqua complexes of Ln3+ with ortho-tetramethyl substituted cucurbituril: Potential applications for isolation of heavier lanthanides. Polyhedron 91:150–154

    Article  CAS  Google Scholar 

  • Zhu Q, Sun YK, Na FS, Wei J, Xu S, Li YL, Guo F (2019) Fabrication of CdS/titanium-oxo-cluster nanocomposites based on a Ti32 framework with enhanced photocatalytic activity for tetracycline hydrochloride degradation under visible light. Appl Catal B 254:541–550

    Article  CAS  Google Scholar 

  • Zhu Q, Sun YK, Xu S, Li YL, Lin XL, Qin YL (2020) Rational design of 3D/2D In2O3 nanocube/ZnIn2S4 nanosheet heterojunction photocatalyst with large-area “high-speed channels” for photocatalytic oxidation of 2,4-dichlorophenol under visible light. J Hazard Mater 382:121098

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank the National Natural Science Foundation of China (No.21961007), the Technology Project of Guizhou Province (QKH[2018]5781-51) and the ‘Chun-Hui’ Fund of Chinese Ministry of Education ([2019]1383) for financial support.

Author information

Authors and Affiliations

  1. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, 550025, People’s Republic of China

    Rui Yi, Xing-Li Liu, Zheng-He Tang, Chao Huang, Bi-Xue Zhu & Chun Zhu

Authors
  1. Rui Yi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xing-Li Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zheng-He Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Chao Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bi-Xue Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Chun Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Bi-Xue Zhu or Chun Zhu.

Additional information

Publisher's Note

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

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yi, R., Liu, XL., Tang, ZH. et al. Anion binding properties for pyrophosphate derived from a 2,6-diamidopyridinedipyrromethane macrocycle. Chem. Pap. 75, 4405–4411 (2021). https://doi.org/10.1007/s11696-021-01554-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-021-01554-6

Keywords

Search

Navigation