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Nanoporous AlSBA-15 catalysed Claisen–Schmidt condensation for the synthesis of novel and biologically active chalcones

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Abstract

Mesoporous AlSBA-15 catalysts (nSi/nAl ratios of 41, 129 and 210) were synthesized by sol–gel method. These materials were characterized by XRD, N2 sorption, FTIR, TPD-NH3, FESEM, EDX, and TEM analysis. XRD analysis of AlSBA-15 catalysts confirmed the existence of well-ordered crystalline structure having p6mm symmetry. N2 sorption isotherm of AlSBA-15 catalysts showed a type IV adsorption isotherm with H1 hysteresis loops. SEM analysis of AlSBA-15 (41) indicated worm-like particle morphology with a size range of 3 μm with co-occurrence of smaller particles of size ca. 1 μm. TEM analysis of AlSBA-15 (41) showed existence of uniform array of tubular nano-channels. The catalytic application of AlSBA-15 catalysts was tested on industrially important chalcones synthesis via Claisen–Schmidt condensation reaction in environment friendly approach. The reaction parameters such as time, temperature, nSi/nAl ratio, catalyst amount, and catalyst stability were investigated. AlSBA-15 (41) catalyst showed an excellent catalytic performance with 98% 1-tetralone conversion with 100% selectivity of compound 1c (91% yield) within 120 min AlSBA-15 (129) and AlSBA-15 (210) catalysts. The anti-oxidant activity of the synthesised chalcones were investigated by various in-vitro procedures, including radical scavenging potentials-1, 1-diphenyl-2-picryl-hydrazil, hydrogen peroxide scavenging, and ferric reducing potential assay. The new chalcone derivatives synthesised in this work showed a very good antioxidant activity and some were found to be more active than the parent chalcones, (E)-3-(4-hydroxy-3-methoxyphenyl)-1-phenylprop-2-en-1-one (compound 8c), and standard antioxidant (curcumin).

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Acknowledgement

One of the authors (G. Chandrasekar) is grateful to the Deanship of Scientific Research of Imam Abdulrahman Bin Faisal University for the financial support under the project (2019-036-Sci).

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Authors and Affiliations

  1. Basic and Applied Scientific Research Center, College of Science, Imam Abdhulrahman Bin Faisal University, P.O. Box 31441, Dammam, Saudi Arabia

    Govindasamy Chandrasekar

  2. Chemistry Division, School of Advanced Sciences, Vellore Institute of Technology, Chennai, India

    Palani Elamathi & M.M. Balamurali

Authors
  1. Palani Elamathi
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  2. Govindasamy Chandrasekar
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  3. M.M. Balamurali
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Correspondence to Govindasamy Chandrasekar or M.M. Balamurali.

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Elamathi, P., Chandrasekar, G. & Balamurali, M. Nanoporous AlSBA-15 catalysed Claisen–Schmidt condensation for the synthesis of novel and biologically active chalcones. J Porous Mater 27, 817–829 (2020). https://doi.org/10.1007/s10934-019-00854-3

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