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Novel optically active 2D materials based on λ-zirconium phosphate and chiral monocarboxylic acids: Synthesis and characterization

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Abstract

Five novel chiral 2D materials with general formula λ-ZrPO4(OH)1-x(RCOO)x(dmso) have been prepared by covalent anchoring of five different chiral carboxylic acids to the sheets of λ-zirconium phosphate (λ-ZrP), namely (S)-(+)-Mandelic acid (MAN), (R)-(−)-α-Methoxyphenylacetic acid (MPA), (S)-(+)-Ibuprofen (IBU), (S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid (MMN) and (−)-Menthyloxyacetic acid (MEN). The synthesized materials were characterized by X-ray diffractometry, FT-IR spectrophotometry, elemental and thermogravimetric analyses and polarimetry. The X-ray diffraction patterns revealed that the interlayer separations increase from 1.02 nm (pure λ-ZrP) to 1.31–2.31 nm as a result of the incorporation of the mentioned acids within the interlayer gallery. The polarimetry measurements showed that the synthesized materials have appreciable optical activities suggesting they could have protentional applications in the field of chiral separation techniques.

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References

  1. Alhendawi, H.M.: Synthesis and structural characterization of a new chiral porous hybrid organic-inorganic material based on γ-zirconium phosphates and L-(+)-phosphoserine. J. Solid State Chem. 201, 24–28 (2013)

    Article  CAS  Google Scholar 

  2. Brunet, E., Alhendawi, H.M., Alonso, M., Cerro, C., Jiménez, L., Juanes, O., Mata, M.J., Salvador, A., Victoria Rodríguez, M., Rodríguez-Payán, E., Rodríguez-Ubis, J.C.: The Use of laminar inorganic salts to make organic molecules display new properties at the supramolecular level in the solid state. J. Phys. 232, 128–136 (2010)

    Google Scholar 

  3. Brunet, E., Alhendawi, H.M., Juanes, O., Rodríguez-Ubis, J.C.: The quest for relationships between conformation and chiroptical properties: from solution to solid state. J. Mex. Chem. Soc. 53(3), 155–162 (2009)

    CAS  Google Scholar 

  4. Brunet, E., Mata, M.J., Juanes, O., Alhendawi, H.M., Cerro, C., Rodríguez-Ubis, J.C.: Solid-state reshaping of nanostructured crystals: supramolecular chirality of layeredm materials derived from polyethylenoxa-pillared zirconium phosphate. Tetrahedron 17(3), 347–354 (2006)

    Article  CAS  Google Scholar 

  5. Brunet, E.: Asymmetric induction under confinement. Chirality 14, 135–143 (2002)

    Article  CAS  Google Scholar 

  6. Leibovitch, M., Olovsson, G., Scheffer, J.R., Trotter, J.: An investigation of the yang photocyclization reaction in the solid state: asymmetric induction studies and crystal structure-reactivity relationships. J. Am. Chem. Soc. 120, 12755–12769 (1998)

    Article  CAS  Google Scholar 

  7. Sellergren, B., Karmalkar, R.N., Shea, K.J.: Enantioselective ester hydrolysis catalysed by imprinted polymers. J. Org. Chem. 65, 4009–4027 (2000)

    Article  CAS  Google Scholar 

  8. Rivera, J.M., Rebek, J., Jr.: Chiral space in a unimolecular capsule. J. Am. Chem. Soc. 122, 7811–7812 (2000)

    Article  CAS  Google Scholar 

  9. Jayaraman, S., Uppili, S., Natarajan, A., Joy, A., Chong, K.C.W., Netherton, M.R., Zenova, A., Scheffer, J.R., Ramamurthy, V.: The influence of chiral auxiliaries is enhanced within zeolites. Tetrahedron Lett. 41, 8231–8235 (2000)

    Article  CAS  Google Scholar 

  10. Yan, Z.H., Li, D., Yin, X.B.: Review for chiral-at-metal complexes and metal-organic framework enantiomorphs. Sci. Bull. 62, 1344–1354 (2017)

    Article  CAS  Google Scholar 

  11. Han, X., Zhang, J., Huang, J., Wu, X., Yuan, D., Liu, Y., Cui, Y.: Chiral induction in covalent organic frameworks. Nat. Commun. 9, 1294–1304 (2018)

    Article  Google Scholar 

  12. Clearfield, A., Stynes, J.A.: The preparation of crystalline zirconium phosphate and some observation on its ion exchange behavior. J. Inorg. Nucl. Chem. 26, 117–129 (1964)

    Article  CAS  Google Scholar 

  13. Clearfield, A., Blessing, R.H., Stynes, J.A.: New crystalline phase of zirconium phosphate possessing ion-exchange properties. J. Inorg. Nucl. Chem. 30, 2249–2258 (1968)

    Article  CAS  Google Scholar 

  14. Poojary, D.M., Zhang, B., Clearfield, A.: Synthesis and crystal structure of a new layered zirconium phosphate compound, Zr(PO4)F(OSME2). J. Chem. Soc. Dalton Trans. 16, 2453–2456 (1994)

    Article  Google Scholar 

  15. Alberti, G., Bartocci, M., Santarelli, M., Vivani, R.: Zirconium phspahte chloride dimethyl sulfoxide, a reactive precursor of a large family of layered compounds. Inorg. Chem. 36, 3574–3575 (1997)

    Article  CAS  Google Scholar 

  16. Alberti, G., Masci, S., Vivani, R.: Layered zirconium phosphate chloride dimethyl sulfoxide as a two-dimensional exchanger of anionic ligands. Part I. Substitution of chloride with inorganic monodentate ligands. Inorg Chem 41, 1913–1919 (2002)

    Article  CAS  Google Scholar 

  17. Alhendawi, H.M.: Synthesis and structural characterization of zirconium phosphate adipate dimethyl sulfoxide: a new lambda-type organic-inorganic layered material. J. Chem. Sci. 126(4), 975–979 (2014)

    Article  CAS  Google Scholar 

  18. Alhendawi, H.M., Brunet, E., Juanes, O., Hammouda, H., Idhair, S., Rodríguez Payán, E., Victoria, R.M.: New soft porous frameworks based on lambda-zirconium phosphate and aliphatic dicarboxylates: synthesis and structural characterization. J. Phys. Chem. Solids 86, 95–100 (2015)

    Article  CAS  Google Scholar 

  19. Alhendawi, H.M.: Lambda-zirconium phosphate covalently pillared with 1,4-biphenyldicarboxylate: a new rigid mesoporous framework. J. Incl. Phenom. Macrocycl. Chem. 85, 187–192 (2016)

    Article  CAS  Google Scholar 

  20. Alhendawi, H.M., Brunet, E., Juanes, O., Idhair, S., Hammouda, H., Rodríguez Payán, E., Victoria, R.M.: Functionalization of lambda-zirconium phosphate with ethylenediaminetetraacetic acid: synthesis, characterization and applications. J. Chem. Sci. 120(6), 1721–1727 (2014)

    Article  Google Scholar 

  21. Caneschi, A., Gatteschi, D., Sangregorio, C., Vaz, M.G.F., Costantino, U., Nocchetti, M., Vivani, R.: Intercalation of a nitronyl nitroxide radical into layered inorganic host. Preparation and physico-chemical characterization. Iorg. Chim. Acta 338, 127–132 (2002)

    Article  CAS  Google Scholar 

  22. Vivani, R., Masci, S., Alberti, G.: Anionic ligand exchange on ZrPO4Cl(dmso): alkoxide and carboxylate derivatives. Inorg. Chem. 43, 368–374 (2004)

    Article  CAS  Google Scholar 

  23. Alhendawi, H.M., Brunet, E., Hammouda, H., Rodríguez-Payan, E.: Intercalation of primary alkylamines into lambda-zirconium phosphate. Lambda-type materials with extended interlayer separation. J. Porous Mater. 23(6), 1519–1526 (2016)

    Article  CAS  Google Scholar 

  24. Poojary, D.M., Shpeizer, B., Clearfield, A.: X-ray powder structure and Rietveld refinement of γ-zirconium phosphate, Zr(PO4)(H2PO4).2H2O. J. Chem. Soc. Dalton Trans. 1, 111–113 (1995)

    Article  Google Scholar 

  25. Alberti, G., Vivani, R., Marmottini, F., Zappelli, P.: Microporous solids based on pillared metal(IV) phosphate and phosphonate. J. Porous Mater. 5, 205–220 (1998)

    Article  CAS  Google Scholar 

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The authors are thankful to the Qatar Charity for financial support.

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Correspondence to Hussein Alhendawi.

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Alhendawi, H., Brunet, E., Payán, E.R. et al. Novel optically active 2D materials based on λ-zirconium phosphate and chiral monocarboxylic acids: Synthesis and characterization. J Incl Phenom Macrocycl Chem 99, 217–226 (2021). https://doi.org/10.1007/s10847-021-01043-z

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