Carborane-based BODIPY dyes: synthesis, structural analysis, photophysics and applications

Frontiers in Chemistry, Год журнала: 2024, Номер 12

Опубликована: Ноя. 5, 2024

Icosahedral boron clusters-based BODIPY dyes represent a cutting-edge class of compounds that merge the unique properties clusters with exceptional fluorescence characteristics dyes. These kinds molecules have garnered substantial interest due to their potential applications across various fields, mainly including optoelectronics, bioimaging, and use as carriers for Boron Neutron Capture Therapy (BNCT). Carborane are known stability, rigid geometry, 3D-aromaticity, while renowned strong absorption, high quantum yields, photostability. The integration carborane into structures leverages stability versatility carboranes enhancing photophysical BODIPY-based fluorophores. This review explores synthesis structural diversity dyes, highlighting how incorporation can lead significant changes in electronic optical We discuss enhanced characteristics, such red-shifted absorption emission poperties, charge transfer effects, improved cellular uptake, resulting from substitution. also delves diverse these compounds. In carborane-BODIPY offer superior internalization, making them ideal cell tracking. photodynamic therapy, (PDT) act potent photosensitizers capable generating reactive oxygen species (ROS) targeted cancer treatment excellent candidates PDT. Additionally, make suitable optoelectronic applications, organic light-emitting diodes (OLEDs) sensors. Overall, versatile promising materials innovation scientific technological applications. aims provide comprehensive overview current state research on synthesis, properties, broad application spectrum.

Язык: Английский

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Bisbenzothieno[b]-fused BODIPYs in panchromatic photoinitiating for the free radical and cationic photopolymerization and application in 3D printing

Polymer Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A family of BODIPY derivatives were reported to exhibit panchromatic behavior for the effective induction polymerization reactions at both ends visible spectrum, e.g. LED@405 nm and LED@660 nm, with practical applications in 3D printing.

Язык: Английский

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A Cascade Strategy for Vinyl Chloride-Substituted BODIPYs with Tunable Photophysical Properties

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An efficient and transition-metal-free method for the synthesis of unprecedented vinyl chloride-substituted BODIPYs has been developed through tandem Friedel-Crafts, enolization chlorination reactions. This transformation offers high regioselectivity stereoselectivity, enabling a variety β-vinyl chloride-β'-acyl- β,β'-divinyl in one-pot reaction at room temperature. Further functionalization gave BODIPY with triphenyl phosphonium moieties, which showed favorable two-photon mitochondrion-targeting imaging capacity living cells intense deep-red fluorescence.

Язык: Английский

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The Quinoline Photoremovable Group (PPG) Platform—A Medicinal Chemist's Approach for Photocage Development and Applications

Medicinal Research Reviews, Год журнала: 2025, Номер unknown

Опубликована: Апрель 12, 2025

Photoremovable protecting groups (PPGs) offer a straightforward solution for the temporary inactivation of biologically active substrates and their subsequent controlled release by light irradiation. Their relatively easy design mode application have made them useful tools studying dynamic biological processes in vitro vivo. Recently, there has been growing body data investigating potential development drug delivery systems. Of various PPG scaffolds use, quinoline photocages history about 20 years. The structure-property relationships PPGs, as well alternative multibranch designs based on monomers thoroughly studied both experimentally theoretically. Therefore, PPGs serve representative study development, showing how applications followed chemical optimization or drove design. Since raison d'être lies light-activated performing structural changes materials, it is crucial to understand are selected utilized end-users, who often not chemists themselves. we discuss whether conclusions drawn from family could lead more general insights field whole. As PPG-related still rely heavily limited number scaffolds, worth considering, what be reasons slow uptake novel scaffolds.

Язык: Английский

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Asymmetric and Symmetric S-zig-zag-Fused BODIPYs: Synthesis and Photophysical and Oxidative Properties

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 18, 2025

We present a new, straightforward, and versatile approach that utilizes regioselective brominated precursors to synthesize both asymmetric symmetric S-zig-zag-fused BODIPYs (s-TFB bis-TFB) in moderate yields (45% 40%, respectively). X-ray structure analyses reveal the planar rigidity of BODIPY skeleton is progressively enhanced with an increasing number thiopyran rings. The annulation S-heteroaromatic rings at zig-zag edge core results blue-shifted absorption emission spectra, bis-TFB exhibiting maxima 530 539 nm elevated LUMO energy levels. In contrast, oxidation s-TFB m-CPBA demonstrates significant site selectivity, affording four products, namely s-s-SFB, s-bis-SFB, bis-s-SFB, bis-bis-SFB, ranging from 22% 36%. These oxidated derivatives display large red-shifted spectra (e.g., 648 735 for s-bis-SFB), along more stable HOMO levels reduced HOMO-LUMO gaps. This cyclization/oxidation strategy enables precise tuning optoelectronic properties, opening new avenues dye design application.

Язык: Английский

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Recent advances in photopharmacology: Harnessing visible light‐activated azobenzene photoswitches

Deleted Journal, Год журнала: 2025, Номер unknown

Опубликована: Апрель 25, 2025

Abstract In the era of precision medicine, photopharmacology that employs molecular photoswitches offers unique opportunities to control action bioactive molecules with high spatiotemporal resolution, while reducing drug side effects, systemic toxicity and emergence resistance. Over past two decades, field has witnessed great achievements in treating blindness, cancer, diabetes, antibiotic resistance, name but a few. Several challenges remain, however, particular fact most photopharmacological agents trigger their activity by Ultraviolet light, which is damaging normal cells poor tissue permeability. Visible light‐activated are hence highly desirable have captured keen recent research interest. This review highlights strategies for synthesis visible light‐responsive azobenzenes (ABs) applications emerging photopharmacology. Such photoswitchable drugs tremendously extend scope future vivo applications. Furthermore, we identify current discuss rational design switches at higher wavelength. We hope inspire further into photochemistry novel based on ABs or other photoswitches, triggered excitation light “phototherapeutic window” 650–900 nm, ultimately enabling full realization these “smart” clinical practice.

Язык: Английский

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Shining light on photo-responsive molecular tools: advances in visible-to-NIR activatable photolabile protecting groups

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

We highlight the recent progress made towards development of visible-to-NIR activatable photolabile caging groups, in which strategies used to red-shift absorption spectra, improve photolysis efficiency and aqueous solubility are described.

Язык: Английский

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Recent Advances of Boron‐Containing Chiral Luminescent Materials^†

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 25, 2024

Comprehensive Summary As a class of organic dyes, boron‐containing compounds play an important role in luminescent materials. They have attracted considerable attention due to their unique photophysical properties. Chiral systems wide range practical applications biological imaging, optoelectronic devices, information storage and 3D display. Boron‐containing chiral materials can not only effectively improve the properties CPL materials, but also bring system, which enables them be used as favorable emitting for expanded applications. Here, we review research progress by detailed discuss according different skeletons, such point chirality, 1,1’‐binaphthyl, [ n ]helicenes, [2,2]paracyclophane pillar[5]arenes. We believe that this is significance development Key Scientists The studies circularly polarized luminescence (CPL) based on small molecules advanced significantly. However, gained recent years. In 2019, Zhao's group prepared binaphthalene derivative modified with triarylborane, representing molecule material exhibit characteristics responsive both solvent fluoride ions. 2020, Chen's steric effects triarylborane triphenylamine prepare planar 2021, Wang's developed new B,N‐embedded double hetero[7]helicenes strong chiroptical responses UV‐visible region. same year, He's asymmetric reactions synthesize boron‐based point‐chirality high efficiency enantioselectivity. 2023, Ravat synthesized 1,4‐B,N‐embedded helicenes exhibiting narrow‐band fluorescence CPL. During period, Matthias Wagner et al obtained (BO) 2 ‐doped tetrathia[7]helicene via efficient four‐step synthesis, Zheng reported nearly pure green electroluminescent device (CP‐OLED). 2024, hetero‐[9]helicenes offering pathway towards significantly enhanced helicene‐based CPEL.

Язык: Английский

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Introducing of an Unexplored Aza-BODIPY Diradicaloids with 4-(2,6-Ditert-butyl)phenoxyl Radicals Located in 1,7-Positions of the Aza-BODIPY Core

Inorganic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 27, 2024

We have prepared and characterized two diradicaloid systems 5a 5b that originated from the oxidation of a 1,7-(4-(2,6-di-tert-butyl)phenol)-substituted aza-BODIPY core. The diradicaloids were by large array experimental computational methods. diamagnetic closed-shell state was postulated as ground in solution solid-state with substantial thermal population originating both open-shell diradical triplet states observed at room temperature. Transient absorption spectroscopy indicates fast (<10 ps) excited deactivation pathways associated target compounds' character Variable-temperature 1H NMR spectra indicate solvent dependency 5b. could be stepwise reduced to mixed-valence radical-anion dianion upon consequent single-electron reductions. Similarly, deprotonated aza-BODIPYs can oxidized form. Both dianionic forms exhibit an intense NIR region. Density functional theory (DFT) time-dependent DFT calculations used explain transformations UV–Vis-NIR all compounds.

Язык: Английский

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Synthesis of Pyridyl Functionalized 3-Pyrolyl BODIPY based Fluoroprobes and Application Towards Highly Selective Detection of Picric Acid

Physical Chemistry Chemical Physics, Год журнала: 2024, Номер 26(34), С. 22479 - 22490

Опубликована: Янв. 1, 2024

A series of pyridyl-coupled 3-pyrrolyl BODIPY fluoroprobes were synthesized by varying the position pyridyl/

Язык: Английский

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