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BODIPY derivatives bearing borneol moieties: Enhancing cell membrane permeability for living cell imaging
摘要： Three novel boron-dipyrromethene (BODIPY) dyes bearing borneol moieties have been designed, synthesized and characterized. The single-crystal structure of the compound 3 was also elucidated for the first time. Their photophysical properties and confocal fluorescence images were investigated by the optical spectroscopy and Confocal fluorescence microscopy. The results indicate that the compounds 2-3 take on high fluorescence quantum yield and cell membrane permeability, which can be utilized as fluorescent visualizers for cell and lysosome fluorescence imaging.
关键词： photophysical properties,borneol,cell imaging,BODIPY,membrane permeability
更新于2025-09-23 15:23:52
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A promising family of fluorescent water-soluble aza-BODIPY dyes for in vivo molecular imaging
摘要： A new family of water-soluble and bioconjugatable aza-BODIPY fluorophores was designed and synthesized using a boron-functionalization strategy. These dissymmetric bis-ammonium aza-BODIPY dyes present optimal properties for a fluorescent probe, i.e. they are highly water-soluble, very stable in physiological medium, they do not aggregate in PBS, possess high quantum yield and finally they can be easily bioconjugated to antibodies. Preliminary in vitro and in vivo studies were performed for one of these fluorophores to image PD-L1 (Programmed Death-Ligand 1), highlighting the high potential of these new probes for future in vivo optical imaging studies.
关键词： molecular Imaging,Fluorescent probes,boron functionalization,aza-BODIPY,Water-soluble fluorophores
更新于2025-09-23 15:23:52
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A molecular hybrid producing simultaneously singlet oxygen and nitric oxide by single photon excitation with green light
摘要： Combination of photosensitizers (PS) for photodynamic therapy with NO photodonors (NOPD) is opening intriguing horizons towards new and still underexplored multimodal anticancer and antibacterial treatments not based on “conventional” drugs and entirely controlled by light stimuli. In this contribution, we report an intriguing molecular hybrid based on a BODIPY light-harvesting antenna that acts simultaneously as PS and NOPD upon single photon excitation with the highly biocompatible green light. The presented hybrid offers a combination of superior advantages with respect to the other rare cases reported to date, meeting most of the key criteria for both PSs and NOPDs in the same molecular entity such as: (i) capability to generate 1O2 and NO with single photon excitation of biocompatible visible light, (ii) excellent 1O2 quantum yield and NO quantum efficiency, (iii) photogeneration of NO independent from the presence of oxygen, (iv) large light harvesting properties in the green region. Furthermore, this compound together with its stable photoproduct, is well tolerated by both normal and cancer cells in the dark and exhibits bimodal photomortality of cancer cells under green light excitation due to the combined action of the cytotoxic 1O2 and NO.
关键词： Green light,Nitric oxide,Multimodal therapy,Singlet oxygen,BODIPY,Photodynamic therapy
更新于2025-09-23 15:22:29
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Novel near-infrared fluorescent liquid crystal: Bodipy bearing multiple alkyl chains with columnar mesophase
摘要： By the typical Knoevenagel condensation of Bodipy with aldehyde derivatives, two novel Bodipy derivatives 3 and 6 with symmetric three and six alkyl chains were designed and prepared. The Bodipy derivative 3 with three alkyl chains showed no mesophase but the Bodipy derivative 6 with six alkyl chains possessed the orderly hexagonal columnar mesophase at room temperature. Both samples 3 and 6 exhibited the near-infrared fluorescence with high fluorescence quantum yields and larger Stokes shifts than their Bodipy precursors. Sample 6 was the first near-infrared fluorescent columnar liquid crystal with Bodipy core. This research presented a good strategy on constructing the near-infrared columnar Bodipy liquid crystal.
关键词： Near-infrared,Bodipy,columnar,mesophase,fluorescence
更新于2025-09-23 15:22:29
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Aggregation-amplified circularly polarized luminescence from axial chiral boron difluoride complexes
摘要： The development of small organic molecules with intense and switchable circularly polarized luminescence (CPL) is currently attracting great interest due to their promising applications in chiroptical devices and sensors. In this paper, CPL-active BF2-bridged azaanthracene dimers (BA1 and BA2) were facilely synthesized by incorporating boron difluoride unit to the bi-naphthalene. BA1 and BA2 show moderate CPL in diluted solutions, however, BA2 exhibited aggregation-amplified red CPL with large dissymmetry factor up to 1.6×10?2. Moreover, acid-/base-triggered CPL switch off/on were also realized via disaggregation/aggregation of BA2 in tetrahydrofuran (THF)/water binary solvents.
关键词： aggregation-induced emission,bodipy,circularly polarized luminescence,switch,dyes and pigments
更新于2025-09-23 15:22:29
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Highly Photostable and Fluorescent Microporous Solids Prepared via Solid-state Entrapment of BODIPY Dyes in a Nascent Metal-Organic Framework
摘要： We report a strategy to synthesize highly emissive, photostable, microporous materials by solid-state entrapment of boron dipyrromethene (BODIPY) fluorophores in a metal-organic framework. Solvent-free mechanochemistry or accelerated aging enabled quantitative capture and dispersal of the PM605 dye within the ZIF-8 framework starting from inexpensive, commercial materials. While the design of emissive BODIPY solids is normally challenged by quenching in a densely-packed environment, herein reported PM605@ZIF-8 materials show excellent emissive properties and to the best of our knowledge an unprecedented ~10-fold enhancement of BODIPY photostability. Time-resolved and steady-state fluorescence studies of PM605@ZIF-8 show that interchromophore interactions are minimal at low dye loadings, but at higher ones through-pore energy transfer between chromophores and to aggregate species lead to quenching.
关键词： fluorescence,metal-organic framework,photostability,BODIPY,microporous materials
更新于2025-09-23 15:21:21
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Self-Assembly of a Carboxyl-Functionalized BODIPY Dye via Hydrogen Bonding
摘要： We report the synthesis, characterization, and self-assembly behavior of a 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dye functionalized at the meso-position with a butyric acid group. Various spectroscopic investigations (UV-Vis, emission, and Fourier-transform infrared spectroscopy (FTIR) studies) supported by X-ray analysis revealed the formation of self-assembled structures in the solid state with translationally stacked BODIPY units driven by hydrogen bonding between the carboxyl groups.
关键词： hydrogen bonding,Self-Assembly,weak non-covalent interactions,BODIPY dyes
更新于2025-09-23 15:21:21
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A computational study on boron dipyromethene ancillary acceptor-based dyes for dye-sensitized solar cells
摘要： A series of (D-π)2-An-A based organic dyes containing boron dipyrromethene (BODIPY) moiety as an ancillary acceptor (An) derivative were chosen, and the effect of donor moieties (diarylamine, carbazole, azepine, and dibenzazepine) was investigated to understand their photophysical and photoelectrochemical properties by employing density functional theory (DFT) and time-dependent DFT. It is experimentally proved that BODIPY enhances the light-harvesting in red and near IR region of visible light. The electron density distribution analysis was performed for all the dyes to confirm the intramolecular charge transfer, envisioned from the simulated absorption spectra of the dyes. Carbazole donor-based dye exhibited the lowest reorganization energy. A dye attached to the TiO2 (1 0 1) surface was modeled to estimate the adsorption energy of the dyes. The density of states analysis revealed that the absence of defect states in the bandgap of TiO2 facilitates the smooth electron transfer from the excited state of the dye to the conduction band of TiO2. Considering the lowest unoccupied molecular orbital (LUMO) energy level of dyes and conduction band energy level of TiO2, it is understood that all the dyes studied in this study are capable of electron injection upon photoexcitation. Considering the driving force for dye regeneration of the dyes and the magnitude of reorganization energy, carbazole donor-based dye (D2) would be the best performing dye in DSSC. Previously, the power conversion efficiencies of the dyes have been reported, and carbazole donor-based dye (D2) exhibited the highest efficiency among all the dyes. Our computational investigations are in good agreement with the experimental results.
关键词： TiO2 (1 0 1) surface,Reorganization energy,DSSC,Dye regeneration,BODIPY
更新于2025-09-23 15:21:01
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Carbazole Green and Blue-BODIPY Dyads and Triads as Donors for Bulk Heterojunction Organic Solar Cells
摘要： Two BODIPY derivatives with one (B2) and two (B3) carbazole moieties were designed, synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV). The optical and electrochemical properties were systematically investigated. These BODIPY dyes exhibit excellent solubility in organic solvents and present high molar extinction coefficients (1.37–1.48 x 105 M-1 cm-1) in solutions with absorption maxima at 586 nm for mono-styryl group and at 672 nm for di-styryl groups. The introduction of the styryl moieties result in a large bathochromic shift and a significant decrease in the HOMO-LUMO energy-gaps. The BODIPY dyes show relatively low HOMO energies ranging from -4.99 to -5.16 eV as determined from cyclic voltammetry measurements. Cyclic voltammetry measurements and theoretical calculations demonstrate that the frontier molecular orbital levels of these compounds match with PC71BM as the acceptors, supporting their application as donor materials in solution-processed small molecule bulk heterojunction (BHJ) organic solar cells. After the optimization of the active layer, B2:PC71BM and B3:PC71BM based organic solar cells showed the overall power conversion efficiency of 6.41% and 7.47%, respectively. The higher PCE of B3 based OSC is ascribed to the more balanced charge transport and exciton dissociation, better crystalline and molecular packing.
关键词： bulk heterojunction,Green and blue-BODIPY,electrochemistry,power conversion efficiency
更新于2025-09-23 15:21:01
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Suppressing the Photocatalytic Activity of Zinc Oxide Electron-Transport Layer in Nonfullerene Organic Solar Cells with a Pyrene-Bodipy Interlayer
摘要： Organic solar cells based on nonfullerene acceptors have recently witnessed a significant rise in their power conversion efficiency values. However, they still suffer from severe instability issues, especially in an inverted device architecture based on the zinc oxide bottom electron transport layers. In this work, we insert a pyrene-bodipy donor?acceptor dye as a thin interlayer at the photoactive layer/zinc oxide interface to suppress the degradation reaction of the nonfullerene acceptor caused by the photocatalytic activity of zinc oxide. In particular, the pyrene-bodipy-based interlayer inhibits the direct contact between the nonfullerene acceptor and zinc oxide hence preventing the decomposition of the former by zinc oxide under illumination with UV light. As a result, the device photostability was significantly improved. The π?π interaction between the nonfullerene acceptor and the bodipy part of the interlayer facilitates charge transfer from the nonfullerene acceptor toward pyrene, which is followed by intramolecular charge transfer to bodipy part and then to zinc oxide. The bodipy-pyrene modified zinc oxide also increased the degree of crystallization of the photoactive blend and the face-on stacking of the polymer donor molecules within the blend hence contributing to both enhanced charge transport and increased absorption of the incident light. Furthermore, it decreased the surface work function as well as surface energy of the zinc oxide film all impacting in improved power conversion efficiency values of the fabricated cells with champion devices reaching values up to 9.86 and 11.80% for the fullerene and nonfullerene-based devices, respectively.
关键词： bodipy,zinc oxide,photocatalytic activity,pyrene,organic solar cells,photostability,nonfullerene acceptors
更新于2025-09-23 15:21:01