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BODIPY Dyes and Their Derivatives

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

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 9279

Special Issue Editor


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Guest Editor
Laboratory of Luminescent Molecular Devices, Ivanovo State University of Chemistry and Technology, 153045 Ivanovo, Russia
Interests: fluorescent molecular systems; BODIPY dyes; aggregation-caused quenching; aggregation-induced emission; chemoinformatics and datasets of fluorescent materials
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Special Issue Information

Dear Colleagues,

The obtainment of optical converters, switches and molecular sensors, including those for biochemical research, as well as therapeutic agents, are currently being identified as the most promising fields in the application of luminophors. The most effective is the use of compounds with intense chromophoric and fluorescent properties, as well as high resistance to aggressive parameters of the solvate environment. Boron dipyrrins (BODIPY) complexes, in addition to the listed characteristics, have prerequisites for structural modification of the ligand periphery, which makes it possible to fine-tune the characteristics of compounds for solving specific practical problems. Due to the high interest in dipyrrin complexes in general, and BODIPY in particular, the development of the chemistry of this group of compounds is currently proceeding at a rapid pace.

Researchers are actively underway to expand the pool of mechanisms for directed modification of the compounds’ characteristics, through the implementation of a variety of mechanisms for intra- and intermolecular energy transfer. The new trend in BODIPY chemistry at the moment is the regulation of monomer-associate/aggregate equilibrium, which leads to reversible changes in the qualitative and quantitative parameters of the spectral characteristics of compounds.

There are efforts to improve the practical properties of compounds by introducing them into matrices, obtaining hybrid materials and conjugates based on these compounds, and expanding the range of applications for solid materials.

Thus, the development of approaches in the production of functional BODIPYs with controllable properties is an urgent task, both from the point of view of fundamental science and for the creation of physicochemical foundations of new technologies and "smart" materials.

In this respect, researchers working in this area are cordially invited to submit their manuscripts relevant to the synthesis, fundamental studies, or applications of BODIPY dyes and their derivatives.

Prof. Dr. Yuriy S. Marfin
Guest Editor

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Keywords

  • BODIPY
  • dipyrrins
  • fluorescent dyes
  • molecular sensors
  • spectral properties

Published Papers (2 papers)

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14 pages, 16105 KiB  
Article
Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors
by Karolina Maleckaitė, Domantas Narkevičius, Rugilė Žilėnaitė, Jelena Dodonova-Vaitkūnienė, Stepas Toliautas, Sigitas Tumkevičius and Aurimas Vyšniauskas
Molecules 2022, 27(1), 23; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27010023 - 21 Dec 2021
Cited by 14 | Viewed by 3681
Abstract
Mapping microviscosity, temperature, and polarity in biosystems is an important capability that can aid in disease detection. This can be achieved using fluorescent sensors based on a green-emitting BODIPY group. However, red fluorescent sensors are desired for convenient imaging of biological samples. It [...] Read more.
Mapping microviscosity, temperature, and polarity in biosystems is an important capability that can aid in disease detection. This can be achieved using fluorescent sensors based on a green-emitting BODIPY group. However, red fluorescent sensors are desired for convenient imaging of biological samples. It is known that phenyl substituents in the β position of the BODIPY core can shift the fluorescence spectra to longer wavelengths. In this research, we report how electron-withdrawing (EWG) and -donating (EDG) groups can change the spectral and sensory properties of β-phenyl-substituted BODIPYs. We present a trifluoromethyl-substituted (EWG) conjugate with moderate temperature sensing properties and a methoxy-substituted (EDG) molecule that could be used as a lifetime-based polarity probe. In this study, we utilise experimental results of steady-state and time-resolved fluorescence, as well as quantum chemical calculations using density functional theory (DFT). We also explain how the energy barrier height (Ea) for non-radiative relaxation affects the probe’s sensitivity to temperature and viscosity and provide appropriate Ea ranges for the best possible sensitivity to viscosity and temperature. Full article
(This article belongs to the Special Issue BODIPY Dyes and Their Derivatives)
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Review

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59 pages, 89901 KiB  
Review
BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment
by Elena Antina, Natalia Bumagina, Yuriy Marfin, Galina Guseva, Liliya Nikitina, Dmitry Sbytov and Felix Telegin
Molecules 2022, 27(4), 1396; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27041396 - 18 Feb 2022
Cited by 48 | Viewed by 4785
Abstract
Fluorescent dyes absorbing and emitting in the visible and near-IR regions are promising for the development of fluorescent probes for labeling and bio-visualization of body cells. The ability to absorb and emit in the long-wavelength region increases the efficiency of recording the spectral [...] Read more.
Fluorescent dyes absorbing and emitting in the visible and near-IR regions are promising for the development of fluorescent probes for labeling and bio-visualization of body cells. The ability to absorb and emit in the long-wavelength region increases the efficiency of recording the spectral signals of the probes due to the higher permeability of the skin layers. Compared to other fluorescent dyes, BODIPYs are attractive due to their excellent photophysical properties–narrow absorption and emission, intense fluorescence, simple signal modulation for the practical applications. As part of conjugates with biomolecules, BODIPY could act as a biomarker, but as therapeutic agent, which allows solving several problems at once-labeling or bioimaging and treatment based on the suppression of pathogenic microflora and cancer cells, which provides a huge potential for practical application of BODIPY conjugates in medicine. The review is devoted to the discussion of the recent, promising directions of BODIPY application in the field of conjugation with biomolecules. The first direction is associated with the development of BODIPY conjugates with drugs, including compounds of platinum, paclitaxel, chlorambucil, isoxazole, capsaicin, etc. The second direction is devoted to the labeling of vitamins, hormones, lipids, and other biomolecules to control the processes of their transport, localization in target cells, and metabolism. Within the framework of the third direction, the problem of obtaining functional optically active materials by conjugating BODIPY with other colored and fluorescent particles, in particular, phthalocyanines, is being solved. Full article
(This article belongs to the Special Issue BODIPY Dyes and Their Derivatives)
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