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p-Sulfonatocalix[8]arene and vitamin C complexation: assessment of photophysical, pKa and antioxidant property

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Abstract

Mode of inclusion complexation of p-sulfonatocalix[8]arene and ascorbic acid in aqueous solution has been investigated in acidic pH based by UV–visible, fluorescence, FT-IR, 1H-NMR and HR-MS spectroscopic studies. Addition of ascorbic acid solution to p-sulfonatocalix[8]arene enhances the fluorescence intensity of p-Sulfonatocalix[8]arene with blue shift in absorption spectra. Hypsochromic shift in absorbance maxima and hyperchromic shift in emission maxima indicates that ascorbic acid experiences less polar microenvironment when bind with SCX8. Binding site and stoichiometry are examined by 1H-NMR and HR-MS techniques. Binding constant (K = 0.42 × 102 M−1) for the inclusion complex is calculated. For complexation, forces like electrostatic attraction, hydrogen bonding and hydrophobic environment of p-sulfonatocalix[8]arene cavity play important role. p-sulfonatocalix[8]arene shows upward pKa shift after binding with Ascorbic acid. The antioxidant property of ascorbic acid has been investigated which shows enhancement by 57% upon complexation with p-sulfonatocalix[8]arene.

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Notes

  1. Kinetic experiments were performed as reported on Ref. 40; the stock solutions of compound (SCX8) were prepared in MeOH. The stoichiometric factors n were calculated (with [DPPH] > [Antioxidant]) from the following equation: n = (DA515/e515)/[Antioxidant] where DA515 is the absorbance difference between the initial and stationary state of DPPH solution, €515 = 10,865 M− 1 cm− 1, and [Antioxidant] is the concentration of antioxidant in cuvette at time zero. The rate constants k1 were thereby obtained from the decay traces using the initial rates at 298 K.

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Acknowledgements

We are thankful to Dr. Pooja J. Doshi, Biochemistry division, Department of chemistry, S. P. Pune University, Pune for measurement of Antioxidant property. We are also thankful to Dr. S. K. Sarkar for his guidance and help for the revision of this manuscript. Thanks are due to Department of Chemistry, S. P. Pune University, Pune for providing facility of NMR, FT-IR, HR-MS.

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  1. Department of Chemistry, Savitribai Phule Pune University, Pune, 411007, India

    Vrashali S. Kalyani & Dipalee D. Malkhede

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Kalyani, V.S., Malkhede, D.D. p-Sulfonatocalix[8]arene and vitamin C complexation: assessment of photophysical, pKa and antioxidant property. J Incl Phenom Macrocycl Chem 87, 179–189 (2017). https://doi.org/10.1007/s10847-016-0689-x

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