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Design and synthesis of bis-coumarinyl methanes from 4-hydroxy-coumarin and aldehydes catalysed by Amberlyst 15 via dual C–C coupling: introducing coumarin based thin film organic nano-materials for memory devices

Research on Chemical Intermediates volume 48, pages 4963–4985 (2022)Cite this article

Abstract

An efficient one pot synthesis of various bis-coumarinyl methane derivatives was investigated by condensing a series of aldehydes with 4-hydroxy coumarin in the presence of Amberlyst 15 catalyst under refluxing conditions in ethanol–water (1:1). This one pot domino Knoevenagel condensation/Micheal addition reaction provides excellent yield of bis-coumarinyl methane derivatives with lots of advantages like shorter reaction time, eco-friendly reaction medium, simple work up, recyclability of the catalyst and chromatography-free purification. Moreover, the synthesized compound was exploited to develop bis-coumarinyl methylene-based nanostructured materials of special interests which were investigated by UV–Vis, fluorescence spectroscopy, imaging in scanning electron microscope and atomic force microscope. Our UV–Vis and fluorescence study indicated that some of the organic compounds are organized as H-aggregate in the thin film. We also investigated I–V characteristics of the thin film of some of the selective compounds which showed write-once-read-more memory switching behaviour onto the thin film under investigations.

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Acknowledgements

One of the authors (SM) gratefully acknowledged the Department of Science and Technology (DST), Govt. of India for providing 400 MHz NMR under DST-FIST programme (No SR/FST/CSI-263/2015) and Central Instrumentation Centre (CIC) Tripura University for other Instrumental facilities.

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Authors and Affiliations

  1. Department of Chemistry, Tripura University, Suryamaninagar, 799 022, India

    Abhijit Rudra Paul & Swapan Majumdar

  2. Department of Physics, Tripura University, Suryamaninagar, 799 022, India

    Surajit Sarkar & Syed Arshad Hussain

  3. Department of Chemistry, Ram Thakur College, Agartala, 799 003, India

    Jewel Hossain

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Rudra Paul, A., Sarkar, S., Hossain, J. et al. Design and synthesis of bis-coumarinyl methanes from 4-hydroxy-coumarin and aldehydes catalysed by Amberlyst 15 via dual C–C coupling: introducing coumarin based thin film organic nano-materials for memory devices. Res Chem Intermed 48, 4963–4985 (2022). https://doi.org/10.1007/s11164-022-04841-3

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