Near‐Infrared Absorbing Aza‐BODIPY Dyes for Optoelectronic Applications

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(15)

Опубликована: Май 11, 2024

Organic dyes that absorb light in the visible to near-infrared region have garnered significant interest, owing their extensive utility organic photovoltaics and various biomedical applications. Aza-boron-dipyrromethene (Aza-BODIPY) are a class of chromophores with impressive photophysical properties such as tunable absorption from towards near infrared (NIR) region, high molar absorptivity, fluorescence quantum yield. In this review, we discuss developments aza-BODIPYs, related synthetic routes, Their design strategies, modifications chemical structures, mode/position attachment, impact on photo-physical reviewed. The potential applications aza-BODIPY derivatives solar cells, photodynamic therapy, boron-neutron capture sensors, photo-redox catalysis, photoacoustic probes optoelectronic devices explained.

Язык: Английский

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Harnessing Dual Phototherapy and Immune Activation for Cancer Treatment: The Development and Application of BODIPY@F127 Nanoparticles

Advanced Healthcare Materials, Год журнала: 2024, Номер 13(28)

Опубликована: Июль 28, 2024

Conventional phototherapeutic agents are typically used in either photodynamic therapy (PDT) or photothermal (PTT). However, efficacy is often hindered by hypoxia and elevated levels of heat shock proteins the tumor microenvironment (TME). To address these limitations, a formylated, near-infrared (NIR)-absorbing heavy-atom-free Aza-BODIPY dye presented that exhibits both type-I type-II PDT actions with high yield reactive oxygen species (ROS) manifests efficient conversion precise adjustments to conjugate structure electron distribution, leading large amount ROS production even under severe hypoxia. improve biosafety water solubility, an amphiphilic triblock copolymer (Pluronic F-127), yielding BDP-6@F127 nanoparticles (NPs) coated. Furthermore, inspired fact phototherapy triggers release tumor-associated antigens, strategy leverages potential immune activation combining PDT/PTT checkpoint blockade (ICB) amplify systemic response achieve much-desired abscopal effect developed. In conclusion, this study presents promising molecular design integrates multimodal therapeutics for effective approach cancer therapy.

Язык: Английский

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Unveiling cellular mysteries: Advances in BODIPY dyes for subcellular imaging

Coordination Chemistry Reviews, Год журнала: 2024, Номер 526, С. 216383 - 216383

Опубликована: Дек. 5, 2024

Язык: Английский

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Synthesis and Photodynamic Activities of Pyridine- or Pyridinium-Substituted Aza-BODIPY Photosensitizers

Journal of Medicinal Chemistry, Год журнала: 2024, Номер 67(17), С. 15908 - 15924

Опубликована: Авг. 21, 2024

In this work, various novel pyridinyl- and pyridinium-modified Aza-BODIPY PSs were designed constructed based on monoiodo (BDP-4 BDP-15) in an attempt to construct "structure-inherent organelles-targeted" endow potential organelle-targeting ability. Pyridinyl displayed potent photodynamic efficacy, monorigidified very effective. The PS 20 with meta-pyridinyl moiety the most photoactivity negligible dark toxicity a favorable dark/phototoxicity ratio (>4800). To our surprise, (e.g., 20) was lipid droplet-targeted. showed good cellular uptake intracellular ROS generation compared BDP-15. preliminary cell death process exploration indicated that resulted peroxidation induced through iron-independent ferroptosis-like pathway. vivo antitumor efficacy experiments manifested significantly inhibited tumor growth outperformed BDP-15 Ce6 even under single low-dose light irradiation (30 J/cm2).

Язык: Английский

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Unveiling new horizons: Exploring rhenium and iridium dipyrrinato complexes as luminescent theranostic agents for phototherapy

Coordination Chemistry Reviews, Год журнала: 2024, Номер 511, С. 215798 - 215798

Опубликована: Апрель 17, 2024

Язык: Английский

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Unveiling the Role of BODIPY Dyes as Small‐Molecule Hole Transport Material in Inverted Planar Perovskite Solar Cells

Solar RRL, Год журнала: 2024, Номер 8(12)

Опубликована: Май 17, 2024

Perovskite solar cells (PSCs) have become a research hotspot since their dramatic increase in power conversion efficiency (PCE), surpassing 26% due to advances cell engineering and interfacial layers. Within the last factor, hole transporting materials play crucial role enhancing device performance stability. Among several molecular building blocks, BODIPYs are attractive for design of novel material (HTMs) outstanding photophysical charge transport properties easily tuned by synthetic modifications. Herein, synthesis five new BODIPY‐based HTMs PyBDP 1–5 reported, functionalized at meso‐ α‐ positions with pyrenyl arylamino units, respectively. The resulting compounds exhibit broad absorption visible region, remarkable thermal stability, narrow bandgaps, suitable energy levels, good extraction capability, as subtracted from experimental computational characterizations. BODIPY derivatives is evaluated planar inverted (p‐ i ‐n) PSCs compared commonly used PTAA, highly efficient systems, reaching PCEs very close that obtained reference polymer (21.51%). incorporation these result an PCE 20.37% devices including PyBDP‐1 19.97% devises containing PyBDP‐3 , thus demonstrating promising alternative obtain simple organic HTMs.

Язык: Английский

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WazaGaY: An Innovative Aza-BODIPY-Derived Near-Infrared Fluorescent Probe for Enhanced Tumor Imaging

Journal of Medicinal Chemistry, Год журнала: 2024, Номер 67(18), С. 16635 - 16648

Опубликована: Сен. 17, 2024

Aza-BODIPYs represent a class of fluorophores in which the π-conjugated system is rigidified and stabilized by boron atom. A promising strategy to enhance their fluorescence properties involves replacing atom with metal ion. Here, we describe synthesis characterization water-soluble derivative where gallium(III) ion, termed WazaGaY (water-soluble aza-GaDIPY). Water solubility ensured two ammonium substituents, inducing bathochromic shift significant increase quantum yield compared that dimethylamino analog. The cellular behavior

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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Halogenated Bis(donor)‐aza‐BODIPY System for Inducing NIR Excitation: Effect of Thiophene and Aminophenyl Donors on Optical Properties and in vitro Tests for Breast Cancer

ChemistrySelect, Год журнала: 2025, Номер 10(3)

Опубликована: Янв. 1, 2025

Abstract A series of near‐IR absorbing BF 2 ‐chelated aza‐boron‐dipyrromethene (AZBs) derivatives bearing aniline/thiophene electron donors were designed, synthesized, and characterized to study the effect substitution on photophysical properties. These molecules exhibit internal charge transfer (ICT) with a characteristic spectrum dual absorption bands which allows electronic excitation in wide spectral region 500–820 nm. The ICT character was stablished by its inhibition upon protonation amino groups trifluoroacetic acid (TFA) CHCl 3 , observed as visible colorimetric change from red blue accompanied an hypsofluoric shift emission band. Protonation AZB‐4 DMSO‐ d 6 addition TFA monitored 1 H, 11 B, 19 F NMR. Thiophene Aza‐BODIPY p ‐(amino) phenyl also generated singlet oxygen ( O ) under irradiation laser light (532 800 nm). generation these dyes enhanced subsequent bromination molecule favors intersystem crossing between triplet states. aza‐BODIPY developed this work have potential applicability photosensitizers photodynamic therapy, sensibility window biomedical interest (700 – 900 nm) excellent photo chemical stability even at high energy irradiation. Additionally, their dark photoinduced cytotoxic activity tested breast cancer cell line (MDA‐MB‐231 cells).

Язык: Английский

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NIR-II absorbing aza-BODIPY with the D-A-A’ framework for PTT/PDT co-therapy

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 111041 - 111041

Опубликована: Март 1, 2025

Язык: Английский

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