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Inclusion induced water solubility and binding investigation of acenaphthene-1,2-dione with p-sulfonatocalix[4]arene

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Abstract

An increase in the water solubility of acenaphthene-1,2-dione (AD) with p-sulfonatocalix[4]arene (p-SC4) is studied by means of simple method using UV chamber and analysed quantitatively using LC. The host guest interaction of AD with p-SC4 is studied using UV–visible absorption and emission spectral studies. The electrochemical properties of AD in the presence of p-SC4 is investigated using cyclic voltammetry method. The mode of binding is investigated using 1H NMR and ROESY techniques. Computational modelling shows that there are various kinds of non-covalent interactions favour the stability of the complexes. The presence of bond critical points between phenyl rings of p-SC4 and AD molecules are confirmed through density functional theory (DFT) and atoms in molecules approaches. Our study clearly reveals that there is strong charge transfer process between p-SC4 (SO3 group) and AD (aryl C-H…O) molecule during the inclusion process. In addition to this, dispersion interaction plays a vital role in the AD absorption on p-SC4 moiety which is confirmed through BE calculations and bond critical points between aromatic clouds.

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Acknowledgements

We acknowledge the financial support of Department of science and Technology (DST INSPIRE) [Project number—IFA14/ CH-147], India and M. Senthilkumaran thanks to DST-PURSE Scheme (No. SR/PURSE Phase 2/38 (G)) for financial assistance. We also thank the financial support from RUSA 2.0 Grant sanctioned vide Letter No. F. 24-51/2014-U, Policy (TNMulti-Gen), Dept. of Edn. Govt. of India, Dt. 09.10.2018.

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Authors and Affiliations

  1. Department of Industrial Chemistry, Alagappa University, Karaikudi, Tamilnadu, India

    Marimuthu Senthilkumaran, Chokalingam Saravanan, Bosco Christin Maria Arputham Ashwin & Paulpandian Muthu Mareeswaran

  2. Department of Chemistry, Pioneer Kumaraswamy College, Nagercoil, Tamilnadu, India

    Bosco Christin Maria Arputham Ashwin

  3. Department of Chemistry, School of Sciences, Tamilnadu Open University, Chennai, India

    Poovan Shanmugavelan

  4. Department of Chemistry, SRM Institute of Science and Technology, Kattankulathur, Tamilnadu, India

    Muthuramalingam Prakash

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  1. Marimuthu Senthilkumaran
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Senthilkumaran, M., Saravanan, C., Ashwin, B.C.M.A. et al. Inclusion induced water solubility and binding investigation of acenaphthene-1,2-dione with p-sulfonatocalix[4]arene. J Incl Phenom Macrocycl Chem 98, 105–115 (2020). https://doi.org/10.1007/s10847-020-01017-7

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