Study of photophysical properties of new asymmetric Meso-BODIPY dimers

This research focuses on the novel synthesis of asymmetric meso -BODIPY dimers, connected at positions 8 and 8'. A novel synthetic route is proposed through the direct coordination of dipyrromethene with a borinic acid which allows the direct functionalization of the boron atom, inspired by previous works. The optical properties of the dimers were compared with the corresponding monomers showing almost no variation at the UV–vis spectra but broad emission bands from 500 to 800 nm that include the typical emissions of each monomer have been observed. The nature of the electronic transitions was studied by computational calculations which support experimental results, providing a profound understanding of structural and photophysical variations. ESP maps, NTOs and dipole moments are shown and support the presence of a charge transfer character transition in the dimers, also hinted by the emission spectra, as well as how these transitions are influenced by the boron attached groups. This innovative approach contributes to the advancement of BODIPY materials, emphasizing the importance of precise synthetic strategies to obtain compounds with promising applications in various fundamental and technological fields.

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Publication Details

Journal
Tetrahedron
Published
2024-12-31
DOI
https://doi.org/10.1016/j.tet.2024.134438
Citations
3
Primary Topic
Luminescence and Fluorescent Materials
Type
article
Field-Weighted Citation Impact
0.35

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Study of photophysical properties of new asymmetric Meso-BODIPY dimers

Rosa Luisa Santillan, Sandra M. Rojas‐Montoya, Oscar González‐Antonio, Norberto Farfán et al.
3 citations
Tetrahedron
Luminescence and Fluorescent Materials
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article

Study of photophysical properties of new asymmetric Meso-BODIPY dimers

Rosa Luisa Santillan, Sandra M. Rojas‐Montoya, Oscar González‐Antonio, Norberto Farfán, Luis Blancarte-Carrazco, Enrique Ordaz-Romero
article en
3 citations

Abstract

This research focuses on the novel synthesis of asymmetric meso -BODIPY dimers, connected at positions 8 and 8'. A novel synthetic route is proposed through the direct coordination of dipyrromethene with a borinic acid which allows the direct functionalization of the boron atom, inspired by previous works. The optical properties of the dimers were compared with the corresponding monomers showing almost no variation at the UV–vis spectra but broad emission bands from 500 to 800 nm that include the typical emissions of each monomer have been observed. The nature of the electronic transitions was studied by computational calculations which support experimental results, providing a profound understanding of structural and photophysical variations. ESP maps, NTOs and dipole moments are shown and support the presence of a charge transfer character transition in the dimers, also hinted by the emission spectra, as well as how these transitions are influenced by the boron attached groups. This innovative approach contributes to the advancement of BODIPY materials, emphasizing the importance of precise synthetic strategies to obtain compounds with promising applications in various fundamental and technological fields.

TetrahedronVol. 172
Universidad Autónoma de la Ciudad de México (MX), Instituto Politécnico Nacional (MX), Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional (MX), Universidad Nacional Autónoma de México (MX)
Consejo Nacional de Ciencia y Tecnología, Universidad Nacional Autónoma de México
Openalex Percentile: Top 42%
Luminescence and Fluorescent Materials
0.35
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