Basic structural modifications for improving the practical properties of BODIPY

Bumagina, Natalia A.; Антина, Е. В.; Ksenofontov, Alexander A.; Antina, L. A.; Kalyagin, Alexander A.; Березин, М. Б.

doi:10.1016/j.ccr.2022.214684

Cited by 60 publications

(30 citation statements)

References 140 publications

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“…Various deep red to NIR chromophores/fluorophores such as squaraine, [19][20][21] azo, [22][23][24] styryl, [25][26][27] perylene, [28][29][30] BODIPY, [31][32][33] aza-BODIPY, [32,34,35] cyanine, [36][37][38] coumarin, [39,40] and xanthene [41][42][43] are reported having either absorption or emission or both lying in the deep-red to NIR. A few such fluorophores are presented in Figure 1.…”

Section: Types Of Deep Red To Nir Chromophores/fluorophoresmentioning

confidence: 99%

Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

Khan

Sekar

2023

ChemistrySelect

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Xanthene dyes exhibit remarkable photophysical properties and photostability. Their ability to switch fluorescence on/off depending on the external environment makes them a promising candidate for imaging/sensing/tracking/labeling probes. However, their emission � 600 nm and Stokes shift ∼ 34 nm restrict their use in biological applications. A wellknown approach to shifting the emission of xanthene dyes in the deep red to Near infrared (NIR) is by forming xanthene hybrids. This review gives a comprehensive list of the deep red to NIR xanthene-hemicyanine and xanthene-coumarin hybrids. We have outlined general synthetic strategies and a detailed discussion of substituent effect, π-conjugation, and ring effect on the photophysical properties of these dyes. A section on applications of deep red to NIR xanthene hybrids based on fluorophore-linker strategy and spirocyclization is included. This review highlights the structure-spectroscopic relationships, which will be useful in designing new deep red to NIR xanthene analogs.

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Section: Types Of Deep Red To Nir Chromophores/fluorophoresmentioning

confidence: 99%

Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

Khan

Sekar

2023

ChemistrySelect

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“…[6][7][8] This variety of physicochemical properties of BODIPYs can be achieved through the accessible route of molecular structure modification. [9][10][11][12][13] For example, the introduction of aryl substituents along the periphery of the BODIPY core leads to a red shift of the absorption and emission maxima, allowing us to use BODIPYs in the ''phototherapeutic window'' region. 12,14 Another example is the halogenation of BODIPYs that realizes promising photosensitizers for cancer photodynamic therapy, using their ability to generate singlet oxygen.…”

Section: Introductionmentioning

confidence: 99%

“…In this regard, the methods based on machine learning (ML) are an attractive alternative. Gao et al suggested a method based on DNN (Deep Neural Network) combining the chemical environment descriptors and the structural descriptors calculated by DFT to predict 1 H/ 13 C NMR chemical shifts of organic molecules. 26 Gerrard et al developed a methodology based on Impression (Intelligent Machine PREdiction of Shift and Scalar information Of Nuclei) KRR (Kernel Ridge Regression) to predict the 15 N NMR chemical shift.…”

Section: Introductionmentioning

confidence: 99%

Accurate prediction of ¹¹B NMR chemical shift of BODIPYs via machine learning

Ksenofontov

Isaev

Lukanov

et al. 2023

Phys. Chem. Chem. Phys.

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“…2 Due to the ease of structural modification based on BODIPY derivatives, it is possible to obtain luminophores that absorb and emit in almost the entire spectral range. 3 Such a set of practically significant physicochemical properties allows the use of dyes in this class in various fields, including molecular sensorics, 4,5 medical diagnostics, [6][7][8] biochemistry, [9][10][11][12] etc.…”

Section: Introductionmentioning

confidence: 99%