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ORIGINAL RESEARCH article

Front. Chem.
Sec. Photocatalysis and Photochemistry
Volume 12 - 2024 | doi: 10.3389/fchem.2024.1407071
This article is part of the Research Topic Light-Induced Transformations in Organic Photochemistry View all articles

Gram-scale photosynthesis of polyfunctionalized dihydro-2-oxypyrroles using 3DPAFIPN as a halogenated dicyanobenzene-based photosensitizer via a consecutive visible-light-induced electron transfer process

Provisionally accepted
Farzaneh Mohamadpour Farzaneh Mohamadpour *Ali Mohammad Amani Ali Mohammad Amani *
  • Shiraz University of Medical Sciences, Shiraz, Iran

The final, formatted version of the article will be published soon.

    Background: Typically, organic dyes show lower excited state lifetimes, a key hindrance in the development of efficient photoredox processes. Due to their distinctive qualities and efficiency, a particular class of organic chromophores has drawn considerable interest from the scientific community. Thermally activated delayed fluorescence (TADF), is only seen in molecules with a minimal energy gap (usually less than 0.2 eV) between their lowest two excited states, i.e., singlet excited state (S1) and triplet excited state (T1), is a distinctive property of the molecules under study. Isophthalonitriles are a promising family of chromophores for use as organic photocatalysts because of the ease with which their redox potentials may be adjusted and the prolonged singlet excited states resulting from TADF. Methods: A sustainable process for the photosynthesis of polyfunctionalized dihydro-2-oxypyrroles has been developed using the Michael-Mannich cyclocondensation of amines, dialkyl acetylenedicarboxylates, and formaldehyde. The development of a green radical synthesis strategy for this family of chemicals is discussed in detail in the current work. This work used a novel halogenated dicyanobenzene-based photosensitizer was used as a photocatalyst. It was dissolved in ethanol, exposed to air at ambient temperature, and triggered by a blue LED as a renewable energy source. This project's main goal is to use a novel conveniently accessible, reasonably priced donor-acceptor (D-A) based on halogenated cyanoarene. Findings: When exposed to visible light, the 3DPAFIPN [2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile] photocatalyst, which is a thermally activated delayed fluorescence (TADF), can induce single-electron transfer (SET), providing a simple and green method that is highly effective, energy-efficient, and environmentally friendly. Also, we calculated the turnover number (TON) and turnover frequency (TOF) for polyfunctionalized dihydro-2-oxypyrroles. Gram-scale cyclization has also been shown to be a practical technique for use in industrial applications.

    Keywords: Dicyanobenzene-based photosensitizer (3DPAFIPN), Polyfunctionalized dihydro-2oxypyrroles, Visible-light-induced electron transfer, Photosynthesis, Renewable energy source

    Received: 26 Mar 2024; Accepted: 10 Jul 2024.

    Copyright: © 2024 Mohamadpour and Amani. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

    * Correspondence:
    Farzaneh Mohamadpour, Shiraz University of Medical Sciences, Shiraz, Iran
    Ali Mohammad Amani, Shiraz University of Medical Sciences, Shiraz, Iran

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