BODIPY Dyes and Their Analogues

Kubota, Yasuhiro

doi:10.1007/978-981-33-4392-4_5

Cited by 5 publications

(2 citation statements)

References 445 publications

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“…Numerous examples have recently been reviewed for polarity sensitive probes of various subcellular structures [ 13 , 14 , 15 , 16 ], reactive oxygen and nitrogen species [ 17 , 18 ], viscosity sensitive probes based on the rotor effect [ 19 , 20 , 21 ] and AIE-effect [ 22 , 23 , 24 ], polarity-controlled triplet photosensitizers for photodynamic therapy [ 25 , 26 , 27 ], photoswitches, and photocages for theranostic applications [ 28 , 29 , 30 , 31 , 32 ], among others. In some cases, the insensitivity of BODIPY sensors to solvent polarity makes them ideal for bioimaging [ 15 , 33 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

Solvatochromic Sensitivity of BODIPY Probes: A New Tool for Selecting Fluorophores and Polarity Mapping

Telegin

Karpova

Makshanova

et al. 2023

IJMS

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This research work is devoted to collecting a high-quality dataset of BODIPYs in a series of 10–30 solvents. In total, 115 individual compounds in 71 solvents are represented by 1698 arrays of the spectral and photophysical properties of the fluorophore. Each dye for a series of solvents is characterized by a calculated value of solvatochromic sensitivity according to a semiempirical approach applied to a series of solvents. The whole dataset is classified into 6 and 24 clusters of solvatochromic sensitivity, from high negative to high positive solvatochromism. The results of the analysis are visualized by the polarity mapping plots depicting, in terms of wavenumbers, the absorption versus emission, stokes shift versus − (absorption maxima + emission maxima), and quantum yield versus stokes shift. An analysis of the clusters combining several dyes in an individual series of solvents shows that dyes of a high solvatochromic sensitivity demonstrate regular behaviour of the corresponding plots suitable for polarity and viscosity mapping. The fluorophores collected in this study represent a high quality dataset of pattern dyes for analytical and bioanalytical applications. The developed tools could be applied for the analysis of the applicability domain of the fluorescent sensors.

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Section: Introductionmentioning

confidence: 99%

Solvatochromic Sensitivity of BODIPY Probes: A New Tool for Selecting Fluorophores and Polarity Mapping

Telegin

Karpova

Makshanova

et al. 2023

IJMS

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“…Heterocycles based on boron difluoride (BF 2 ) adducts of chelating N -donor ligands are molecular materials that offer useful and potentially tunable redox, absorption, and emission properties. Perhaps the most well-known of these materials are the boron dipyrromethenes (BODIPYs), which have been highly sought after due to their narrow absorption and emission profiles, very high emission quantum yields (Φ em ) in solution, and rich redox chemistry. − BODIPYs have been incorporated into molecular materials with an A–D–A architecture ( e.g. , 3 ) and exhibit near-infrared absorption and emission, electrochemical band gaps (E g CV ) as low as 1.67 eV, and the ability to generate singlet oxygen .…”

Section: Introductionmentioning

confidence: 99%

Tuning the Properties of Donor–Acceptor and Acceptor–Donor–Acceptor Boron Difluoride Hydrazones via Extended π-Conjugation

2022

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Molecular materials with π-conjugated donor–acceptor (D–A) and acceptor–donor–acceptor (A–D–A) electronic structures have received significant attention due to their usage in organic photovoltaic materials, in organic light-emitting diodes, and as biological imaging agents. Boron-containing molecular materials have been explored as electron-accepting units in compounds with D–A and A–D–A properties as they often exhibit unique and tunable optoelectronic and redox properties. Here, we utilize Stille cross-coupling chemistry to prepare a series of compounds with boron difluoride hydrazones (BODIHYs) as acceptors and benzene, thiophene, or 9,9-dihexylfluorene as donors. BODIHYs with D–A and A–D–A properties exhibited multiple reversible redox waves, solid-state emission with photoluminescence quantum yields up to 10%, and aggregation-induced emission (AIE). Optical band gaps (or highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) gaps) determined for these compounds (2.02–2.25 eV) agree well with those determined from cyclic voltammetry experiments (2.05–2.42 eV). The optoelectronic properties described herein are rationalized with density functional theory calculations that support the interpretation of the experimental findings. This work provides a foundation of understanding that will allow for the consideration of D–A and A–D–A BODIHYs to be incorporated into applications ( e.g. , organic electronics) where fine-tuning of band gaps is required.

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Synthesis, Structures and Photophysical Properties of Asymmetric Fulvene‐[b]‐fused BODIPYs

Zhao,

Xu,

et al. 2024

Chemistry A European J

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Herein, we developed a one‐pot procedure to synthesize novel fulvene‐[b]‐fused BODIPYs from α‐(2‐alkynylphenyl)‐pyrrole and acylpyrrole, using 5‐exo cyclization as the key transformation. Compared to benzene‐[b]‐fused BODIPYs, although they have similar chemical compositions, their structures and properties significantly differ from each other, which can be attributed to the less aromaticity of the fulvene linker than benzene. Notably, fulvene‐[b]‐fused BODIPY 1b exhibits helical‐twisted core skeleton, intensified red‐shifted absorption, and peak fluorescence. In addition, the pathway of this one‐pot reaction and the mechanism of POCl3 mediated 5‐exo cyclization have been proposed by a combining experimental and computational study.

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BODIPY Dyes and Their Analogues

Cited by 5 publications

References 445 publications

Solvatochromic Sensitivity of BODIPY Probes: A New Tool for Selecting Fluorophores and Polarity Mapping

Solvatochromic Sensitivity of BODIPY Probes: A New Tool for Selecting Fluorophores and Polarity Mapping

Tuning the Properties of Donor–Acceptor and Acceptor–Donor–Acceptor Boron Difluoride Hydrazones via Extended π-Conjugation

Synthesis, Structures and Photophysical Properties of Asymmetric Fulvene‐[b]‐fused BODIPYs

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