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9-mesityl-10-methylacridinium perchlorate (Mes-Acr-Me+ClO4−) as a novel metal-free donor–acceptor (D–A) photocatalyst: visible-light-induced access to tetrahydrobenzo[b]pyran scaffolds through a single-electron transfer (SET) pathway

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Abstract

A green radical synthetic approach for the production of tetrahydrobenzo[b]pyran scaffolds, which utilizes a Knoevenagel–Michael cyclocondensation reaction of aldehydes, malononitrile, and dimedone, has been devised. This innovative technique has been designed to achieve environmental sustainability. A novel single-electron transfer photocatalyst was employed for the synthesis in an aqueous ethanol solution under an air atmosphere at room temperature and stimulated with blue LED illumination serving as a renewable energy source. The objective of this undertaking is to cultivate a metal-free donor–acceptor (D–A) photocatalyst that is highly affordable and universally accessible. 9-Mesityl-10-methylacridinium perchlorate (Mes-Acr-Me+ClO4−) is recognized for its expeditious and effortless applicability, high efficiency in yielding products, low energy consumption, and commendable eco-friendliness. This capability facilitates the investigation into the temporal alterations of environmental and chemical constituents. A research inquiry was conducted with the primary objective of determining the turnover number and turnover frequency associated with tetrahydrobenzo[b]pyran scaffolds. Furthermore, the attainment of cyclization at a gram-scale level offers substantiation for its feasibility as a viable solution for industrial implementation.

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Fig. 1
Fig. 2
Scheme 1
Scheme 2

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Acknowledgements

This work is financially supported by Iran National Science Foundation (INSF) (No. 4015618), financially supported by Iran’s National Elites Foundation (No. 4015618), and also, Shiraz University of Medical Sciences.

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The authors received no specific funding for this work.

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Authors and Affiliations

  1. Department of Medical Nanotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical Sciences, Shiraz, Iran

    Farzaneh Mohamadpour & Ali Mohammad Amani

  2. Facultad de Arquitectura y Urbanismo, Universidad UTE Calle Rumipamba S/N y Bourgeois, 170147, Quito, Ecuador

    Hesam Kamyab

  3. Department of Biomaterials, Saveetha Dental College and Hospital, Saveetha Institute of Medical and Technical Sciences, Chennai, 600 077, India

    Hesam Kamyab

  4. Faculty of Chemical and Energy Engineering, Faculty of Engineering, Process Systems Engineering Centre (PROSPECT), Universiti Teknologi Malaysia, Skudai, Johor, Malaysia

    Hesam Kamyab

  5. Engineering Department, Razak Faculty of Technology and Informatics, Universiti Teknologi Malaysia, Jln Sultan Yahya Petra, 54100, Kuala Lumpur, Malaysia

    Shreeshivadasan Chelliapan

Authors
  1. Farzaneh Mohamadpour
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  2. Hesam Kamyab
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  3. Shreeshivadasan Chelliapan
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  4. Ali Mohammad Amani
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Contributions

F.M. and H.K. and Sh.Ch. and A.M.A. wrote the main manuscript text and F.M. and H.K. and Sh.Ch. and A.M.A. prepared figures 1-4. All authors reviewed the manuscript.

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Correspondence to Farzaneh Mohamadpour, Shreeshivadasan Chelliapan or Ali Mohammad Amani.

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Mohamadpour, F., Kamyab, H., Chelliapan, S. et al. 9-mesityl-10-methylacridinium perchlorate (Mes-Acr-Me+ClO4−) as a novel metal-free donor–acceptor (D–A) photocatalyst: visible-light-induced access to tetrahydrobenzo[b]pyran scaffolds through a single-electron transfer (SET) pathway. Res Chem Intermed (2024). https://doi.org/10.1007/s11164-024-05304-7

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