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The Chemistry of BODIPY Today
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The Chemistry of BODIPY Today

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 June 2023) | Viewed by 10684

Special Issue Editors

Dr. Massimiliano Cordaro

E-Mail Website
Guest Editor
Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Messina, Italy
Interests: organic synthesis; NMR spectroscopy; chromophores; BODIPY; heterocyclic chemistry; laboratory methodologies; polymer functionalization; organic physical chemistry
Dr. Fausto Puntoriero

E-Mail Website
Guest Editor
Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Messina, Italy
Interests: supramolecular photochemistry/photophysics; solar energy conversion; synthesis of polypyridine multinuclear metal complexes; BODIPY; ultrafast spectroscopy; energy and electron transfer; electrochemistry; photocatalysis and bioimaging
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The fascinating world of color has always attracted humans toward developing a deeper understanding of nature. The origin of knowledge is founded on the observation of changes in nature and analyzed and interpreted mainly through techniques involving light. In line with this concept, natural and synthetic dyes are studied and used for various purposes, and among these, the BODIPY are the most versatile, especially with regard to the possibility of various structural modifications that are translated into a fine-tuning of their photophysical features. Today, the possible applications based on BODIPY dyes, such as probes for bioimaging, biological labels, potential agents for photodynamic therapy, fluorescent indicators, tunable lasers dyes, solar light-harvesting antennas, or components of solar cells, are widely recognized. Thanks to the outstanding properties attributed to the boron complexes of dipyrromethenes, successful applications are ever-increasing, and numerous new examples of finely tuned molecules are reported. This Special Issue aims to collect recent scientific research, be it in the form of full-articles, communications or mini-reviews, to improve our understanding of future trends in BODIPY derivative applications.


Dr. Massimiliano Cordaro
Dr. Fausto Puntoriero
Guest Editors

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Keywords

  • BODIPY
  • aza-BODIPY
  • dipyrromethenes 
  • luminescence
  • energy/electron transfer
  • bio-imaging
  • solar energy conversion
  • sensors
  • sensitizers

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Published Papers (4 papers)

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Research

22 pages, 5160 KiB  
Article
BF2-Azadipyrromethene Fluorophores for Intraoperative Vital Structure Identification
by Cathal Caulfield, Dan Wu, Ian S. Miller, Annette T. Byrne, Pól Mac Aonghusa, Sergiy Zhuk, Lorenzo Cinelli, Elisa Bannone, Jacques Marescaux, Sylvain Gioux, Michele Diana, Taryn L. March, Alexander L. Vahrmeijer, Ronan Cahill and Donal F. O’Shea
Molecules 2023, 28(5), 2167; https://doi.org/10.3390/molecules28052167 - 25 Feb 2023
Cited by 3 | Viewed by 2154
Abstract
A series of mono- and bis-polyethylene glycol (PEG)-substituted BF2-azadipyrromethene fluorophores have been synthesized with emissions in the near-infrared region (700–800 nm) for the purpose of fluorescence guided intraoperative imaging; chiefly ureter imaging. The Bis-PEGylation of fluorophores resulted in higher aqueous fluorescence [...] Read more.
A series of mono- and bis-polyethylene glycol (PEG)-substituted BF2-azadipyrromethene fluorophores have been synthesized with emissions in the near-infrared region (700–800 nm) for the purpose of fluorescence guided intraoperative imaging; chiefly ureter imaging. The Bis-PEGylation of fluorophores resulted in higher aqueous fluorescence quantum yields, with PEG chain lengths of 2.9 to 4.6 kDa being optimal. Fluorescence ureter identification was possible in a rodent model with the preference for renal excretion notable through comparative fluorescence intensities from the ureters, kidneys and liver. Ureteral identification was also successfully performed in a larger animal porcine model under abdominal surgical conditions. Three tested doses of 0.5, 0.25 and 0.1 mg/kg all successfully identified fluorescent ureters within 20 min of administration which was sustained up to 120 min. 3-D emission heat map imaging allowed the spatial and temporal changes in intensity due to the distinctive peristaltic waves of urine being transferred from the kidneys to the bladder to be identified. As the emission of these fluorophores could be spectrally distinguished from the clinically-used perfusion dye indocyanine green, it is envisaged that their combined use could be a step towards intraoperative colour coding of different tissues. Full article
(This article belongs to the Special Issue The Chemistry of BODIPY Today)
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15 pages, 5174 KiB  
Article
Identifying STEDable BF2-Azadipyrromethene Fluorophores
by Niamh Curtin, Massimiliano Garre, Dan Wu and Donal F. O’Shea
Molecules 2023, 28(3), 1415; https://doi.org/10.3390/molecules28031415 - 2 Feb 2023
Viewed by 1819
Abstract
BF2-azadipyrromethenes are highly versatile fluorophores used for cellular and in vivo imaging in the near-infrared and far-red regions of the spectrum. As of yet, their use in conjunction with super-resolution imaging methodologies has not been explored. In this report, a series [...] Read more.
BF2-azadipyrromethenes are highly versatile fluorophores used for cellular and in vivo imaging in the near-infrared and far-red regions of the spectrum. As of yet, their use in conjunction with super-resolution imaging methodologies has not been explored. In this report, a series of structurally related BF2-azadipyrromethenes has been examined for their suitability for use with stimulated emission depletion (STED) nanoscopy. The potential for STED imaging was initially evaluated using aqueous solutions of fluorophores as an effective predictor of fluorophore suitability. For live cell STED imaging in both 2D and 3D, several far-red emitting BF2-azadipyrromethenes were successfully employed. Image resolution below the diffraction limit of a confocal microscope was demonstrated through measurement of distinct intracellular features including the nuclear membrane, nuclear lamina invaginations, the endoplasmic reticulum, and vacuoles. As the STED ability of BF2-azadipyrromethene fluorophores has now been established, their use with this super-resolution method may be expected to increase in the future. Full article
(This article belongs to the Special Issue The Chemistry of BODIPY Today)
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13 pages, 3671 KiB  
Article
Synthetic Exploration of Bis(phenolate) Aza-BODIPYs and Heavier Group 13 Chelates
by Aiden M. Lane, Ny T. C. Luong, Jordan C. Kelly, Martin J. Neal, Jeremiah Jamrom, Aaron J. Bloomfield, Paul A. Lummis, Thomas D. Montgomery and Daniel T. Chase
Molecules 2022, 27(23), 8256; https://doi.org/10.3390/molecules27238256 - 26 Nov 2022
Cited by 2 | Viewed by 2920
Abstract
A series of boron, aluminum, gallium, and indium chelates containing the underexplored bis(phenolate) aza-dipyrromethene (aza-DIPY) core were prepared. These compounds were found to possess near-infrared absorption and emission profiles in the 710 to 770 nm domain and exhibit quantum yield values up to [...] Read more.
A series of boron, aluminum, gallium, and indium chelates containing the underexplored bis(phenolate) aza-dipyrromethene (aza-DIPY) core were prepared. These compounds were found to possess near-infrared absorption and emission profiles in the 710 to 770 nm domain and exhibit quantum yield values up to 14%. X-ray diffraction analysis revealed that heavier group 13 bis(phenolate) aza-DIPY chelates possessed octahedral geometries with either THF or pyridine groups occupying the axial positions as opposed to the tetrahedral geometry of the boron chelate. Full article
(This article belongs to the Special Issue The Chemistry of BODIPY Today)
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11 pages, 1925 KiB  
Article
A Computational-Experimental Approach to Unravel the Excited State Landscape in Heavy-Atom Free BODIPY-Related Dyes
by Esther Rebollar, Jorge Bañuelos, Santiago de la Moya, Julien Eng, Thomas Penfold and Inmaculada Garcia-Moreno
Molecules 2022, 27(15), 4683; https://doi.org/10.3390/molecules27154683 - 22 Jul 2022
Cited by 3 | Viewed by 2673
Abstract
We performed a time-gated laser-spectroscopy study in a set of heavy-atom free single BODIPY fluorophores, supported by accurate, excited-state computational simulations of the key low-lying excited states in these chromophores. Despite the strong fluorescence of these emitters, we observed a significant fraction of [...] Read more.
We performed a time-gated laser-spectroscopy study in a set of heavy-atom free single BODIPY fluorophores, supported by accurate, excited-state computational simulations of the key low-lying excited states in these chromophores. Despite the strong fluorescence of these emitters, we observed a significant fraction of time-delayed (microseconds scale) emission associated with processes that involved passage through the triplet manifold. The accuracy of the predictions of the energy arrangement and electronic nature of the low-lying singlet and triplet excited states meant that an unambiguous assignment of the main deactivation pathways, including thermally activated delayed fluorescence and/or room temperature phosphorescence, was possible. The observation of triplet state formation indicates a breakthrough in the “classic” interpretation of the photophysical properties of the renowned BODIPY and its derivatives. Full article
(This article belongs to the Special Issue The Chemistry of BODIPY Today)
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