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ORIGINAL RESEARCH article

Front. Chem.
Sec. Organic Chemistry
Volume 12 - 2024 | doi: 10.3389/fchem.2024.1488933
This article is part of the Research Topic Synthesis, Structural Analysis, and Conformational Behavior of BODIPY Dyes and Their Congeners View all 4 articles

Synthesis of BODIPY-pyrrolo[3,4-b]pyridin-5-ones via Ugi-Zhu/cascade reactions and studies of fluorescence response toward viscosity

Provisionally accepted
Julio C. Flores-Reyes Julio C. Flores-Reyes 1Annia Galano Annia Galano 1Sandra M. Rojas-Montoya Sandra M. Rojas-Montoya 2Luis Blancarte-Carrazco Luis Blancarte-Carrazco 2Elba Xochitiotzi-Flores Elba Xochitiotzi-Flores 2Héctor García-Ortega Héctor García-Ortega 2Norberto Farfán Norberto Farfán 2*Alejandro Islas-Jácome Alejandro Islas-Jácome 1*Eduardo González-Zamora Eduardo González-Zamora 1*
  • 1 Departamento de Química, Universidad Autónoma Metropolitana, Mexico City, Mexico
  • 2 Faculty of Chemistry, National Autonomous University of Mexico, Mexico City, México, Mexico

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

    A series of seven new meso-phenyl pyridin-5-one conjugates were synthesized in one experimental step by using a Sc(III)-catalyzed Ugi-Zhu three-component reaction coupled to a cascade sequence (aza Diels-Alder / N-acylation / aromatization) as post-MCR functionalization process. Further experimental studies were performed behind understanding the fluorescence response toward viscosity. All compounds exhibited a linear response between increasing viscosity (DMSO and glycerol mixtures) and fluorescence intensity. The different substituents also influenced the photophysical properties. Furthermore, in DMSO all compounds exhibited dual emission. Each band is attributed to the pyrrolo [3,4-b]pyridin-5-one and BODIPY moieties, respectively. The electronic structure of all compounds was computed by DFT and TD-DFT calculations, allowing to determine the molecular orbitals involved in the electronic transitions.

    Keywords: multicomponent reaction, BODIPY, fluorescence, Viscosity, Polyheterocycle

    Received: 30 Aug 2024; Accepted: 07 Oct 2024.

    Copyright: © 2024 Flores-Reyes, Galano, Rojas-Montoya, Blancarte-Carrazco, Xochitiotzi-Flores, García-Ortega, Farfán, Islas-Jácome and González-Zamora. 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:
    Norberto Farfán, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City, 04510, México, Mexico
    Alejandro Islas-Jácome, Departamento de Química, Universidad Autónoma Metropolitana, Mexico City, Mexico
    Eduardo González-Zamora, Departamento de Química, Universidad Autónoma Metropolitana, Mexico City, Mexico

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