Synthesis of BODIPY-pyrrolo[3,4-]pyridin-5-ones Ugi-Zhu/cascade Reactions and Studies of Fluorescence Response Toward Viscosity

Overview

Journal Front Chem

Specialty Chemistry

Date 2024 Nov 4

PMID 39494394

Authors

Julio C Flores-Reyes

Annia Galano

Sandra M Rojas-Montoya

Luis Blancarte-Carrazco

Elba Xochitiotzi-Flores

Hector Garcia-Ortega

Norberto Farfan

Alejandro Islas-Jacome

Eduardo Gonzalez-Zamora

Affiliations

Soon will be listed here.

Abstract

A series of seven new -phenyl BODIPY-pyrrolo[3,4-]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 ( Diels-Alder/-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-]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.

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