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Effect of Alkyl, Aryl, and meso-Aza Substitution on the Thermal Stability of BODIPY
摘要： The effect of peripheral alkyl, aryl, and meso-aza substitution on the thermal stability of BODIPYs in an argon or oxygen atmosphere has been analyzed using thermogravimetric study results. It has been shown that an increase in the length of 2,6-alkyl substituents to seven carbon atoms is accompanied by the growth of BODIPY thermal stability by 80°C. The greatest increase in the destruction temperature of BODIPY (by 100°C) is attained via the introduction of phenyl groups in the 1,3,5,7-positions of its dipyrromethenmethene framework. meso-Aza substitution does not almost produce any effect on the thermal stability of BODIPY dyes. The BODIPY destruction beginning temperature decreases by 60–90°C in the presence of air oxygen. The thermal stability of BODIPY tends to decrease with reducing degree and symmetry of alkyl substitution in the dipyrromethene framework. A lower thermal stability of BODIPY in comparison with zinc(II) dipyrromethenates is due to the participation of fluorine atoms in intramolecular redox processes.
关键词： phenyl substituents,thermal stability,structural,BODIPY,alkyl,aza-dipyrromethene,dipyrromethenmethene
更新于2025-09-23 15:21:01
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L-cystine-linked BODIPY-adsorbed monolayer MoS2 quantum dots for ratiometric fluorescent sensing of biothiols based on the inner filter effect
摘要： This study fabricated a dual-emission probe consisting of monolayer MoS2 quantum dots (M-MoS2 QDs) and L-cystine-linked boron-dipyrromethene (L-Cys-BODIPY) molecules for ratiometric sensing of biothiols, thiol product-related enzyme reactions, and ratiometric imaging of glutathione (GSH)-related reactions in HeLa cells. The formation of L-Cys-BODIPY-adsorbed M-MoS2 QDs (named as BODIPY-M-MoS2 QDs) was demonstrated by comparing them with M-MoS2 QDs using transmission electron microscopy, atomic force microscopy, and X-ray photoelectron spectroscopy. The BODIPY-M-MoS2 QDs exhibited dual-emission bands, excellent biocompatibility, and good resistance to photobleaching. It was found that the adsorbed L-Cys-BODIPY molecules rarely quenched the fluorescence of M-MoS2 QDs, and meanwhile, they were self-quenched by π-π stacking between each BODIPY backbones. The presence of biothiols induced the reduction of weakly fluorescent L-Cys-BODIPY to strongly fluorescent of L-cysteine-conjugated BODIPY. Since having a much higher molar absorption coefficient than L-Cys-BODIPY, the liberated L-cysteine-conjugated BODIPY behaved as an effective inner filter to absorb the excitation light and subsequently quenched the fluorescence of M-MoS2 QDs. The appearance of L-cysteine-conjugated BODIPY could barely affected to the fluorescence lifetime of M-MoS2 QDs, confirming the inner filter effect of L-cysteine-conjugated BODIPY onto the fluorescence of M-MoS2 QDs. The present probe not only provided a linear ratiometric response to 1–10 mM GSH, 1-10 μM cysteine, and 1-10 μM of homocysteine but also remarkably showed the ratiometric detection of thiol products from the reactions of 1–900 units L-1 S-adenosylhomocysteine (SAH) hydrolase and SAH as well as 1-850 units L-1 GSH reductase and disulfide GSH. Additionally, the present probe was well-suited for ratiometric imaging of intracellular GSH levels in non-treated and drug-treated HeLa cells
关键词： ratiometric imaging,BODIPY,biothiols,ratiometric sensor,MoS2 quantum dots,enzymatic reaction
更新于2025-09-23 15:21:01
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Conjugated Polymers Containing BODIPY and Fluorene Units for Sensitive Detection of CN? Ions: Site-Selective Synthesis, Photo-Physical and Electrochemical Properties
摘要： Conjugated polymers containing distinct molecular units are expected to be very interesting because of their unique properties endowed by these units and the formed conjugated polymers. Herein, four new conjugated copolymers based on fluorene and 4,4’-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) have been designed and synthesized via Sonogashira polymerization. The fluorene unit was attached to the 3,5- or 2,6-positions of BODIPY by ethynylenes or p-diacetylenebenzene. The obtained polymers show good thermal stability and broad absorption in the wavelength range from 300 to 750 nm. The effects of site-selective copolymerization and conjugation length along the polymer backbone on the optoelectronic and electrochemical properties of these copolymers were systematically studied by UV-Vis spectroscopy, photoluminescence (PL) and cyclic voltammetry. Besides, it is found that the BODIPY-based copolymers exhibit selectively sensitive responses to cyanide anions, resulting in obvious change of UV-Vis absorption spectra and significant fluorescence quenching of the polymers among various common anions.
关键词： conjugated copolymers,site-selective,cyanide anion,BODIPY
更新于2025-09-23 15:21:01
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Synthesis and Spectral Characteristics of BODIPY Dyes with Two or Three Dipyrrin Domains
摘要： Several boron-dipyrrin (BODIPY) based fluorophores with two and three dipyrrin cores were synthesized and investigated in solvents under the concentration variation. Comparative analysis of spectral and photophysical changes under increasing the number of the cores in the dye molecule was made. Mutual influence of dipyrrin cores was detected leading to the increasing of the compounds rigidity and, thus, the absence of fluorescent molecular rotor effects under the viscosity variation. Aggregation induced quenching, which was observed for many mono-domain BODIPY dyes is reduced in case of investigated poly-domain compounds.
关键词： Aggregation induced spectral changes,Intramolecular rotation,Spectral properties,Synthesis,BODIPY
更新于2025-09-23 15:21:01
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Redox-Switchable Cyan Fluorescence of a BODIPY Analog Inspired by Propentdyopent Pigments
摘要： The combination of reversible redox chemistry and bright redox-responsive emission properties is key to the development of electrofluorochromic switches for applications in bioimaging and optoelectronics. Herein, the redox-active dipyrrin-1,9-dione fragment, which is characteristic of the propentdyopent family of heme metabolites and urinary pigments, is employed for the synthesis of a BODIPY analog. This boron difluoride complex exhibits bright fluorescence in organic solvents and a significant ipsochromic shift to the cyan region when compared to typical green BODIPY dyes. Electrochemical and spectroscopic measurements show that the dipyrrindione ligand acts as an electron reservoir by hosting an unpaired spin upon one-electron reduction. This ligand-based redox event reversibly abolishes the fluorescence emission, thus switching off the novel electrofluorochromic system.
关键词： Redox chemistry,Switches,BODIPY,Fluorescence,Dyes/Pigments
更新于2025-09-23 15:21:01
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Rational design of pyrrolopyrrole-aza-BODIPY-based acceptora??donora??acceptor triads for organic photovoltaics application
摘要： Acceptor-donor-acceptor triads consisting of diketopyrrolopyrrole (DPP) or pyrrolopyrrole aza-BODIPY (PPAB) or both as acceptors and cyclopentadithiophene as a donor were rationally designed for near infrared (NIR) photovoltaics application. Among them, the PPAB-based triad exhibited the highest power conversion efficiency of 3.88% owing to the panchromatic absorption in the UV/vis/NIR regions.
关键词： pyrrolopyrrole-aza-BODIPY,organic photovoltaics,acceptor-donor-acceptor triads,near infrared photovoltaics
更新于2025-09-23 15:19:57
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Use of BODIPY-Labeled ATP Analogues in the Development and Validation of a Fluorescence Polarization-Based Assay for Screening of Kinase Inhibitors
摘要： The screening of compound libraries to identify small-molecule modulators of specific biological targets is crucial in the process for the discovery of novel therapeutics and molecular probes. Considering the need for simple single-tool assay technologies with which one could monitor “all” kinases, we developed a fluorescence polarization (FP)-based assay to monitor the binding capabilities of protein kinases to ATP. We used BODIPY ATP-y-S as a probe to measure the shift in the polarization of a light beam when passed through the sample. We were able to optimize the assay using commercial Protein Kinase A (PKA) and H7 efficiently inhibited the binding of the probe when added to the reaction. Furthermore, we were able to employ the assay in a high-throughput fashion and validate the screening of a set of small molecules predicted to dock into the ATP-binding site of PKA. This will be useful to screen larger libraries of compounds that may target protein kinases by blocking ATP binding.
关键词： high-throughput screening,ATP-binding site,protein kinases,fluorescence polarization,BODIPY ATP-y-S
更新于2025-09-23 15:19:57
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Excitonically Coupled Cyclic BF2 Arrays of Calix[8]a?? and Calix[16]phyrin as Neara??IRa?? Chromophores
摘要： A pair of giant calix[n]phyrin derivatives namely calix[8]- (4) and calix[16]phyrin (5), involving two and four BF2 units, respectively, were prepared via the condensation of bis-naphthobipyrrolylmethene-BF2 complex with pentafluorobenzaldehyde. Both systems and precursor 3 were fully characterized, including via single crystal X-ray diffraction analyses. Calix[n]phyrins 4 and 5 display extremely high extinction coefficients (3.67 and 4.82 105 M-1cm-1, respectively) in the near-IR region. This observation was taken as initial evidence for strong excitonic coupling within these cyclic multi-chromophoric systems. Detailed insights into the effect of excitonic coupling dynamics on the electronic structure and photophysical properties of the macrocycles came from fluorescence, time-correlated single-photon counting (TCSPC) and transient absorption (TA) measurements. Support for the experimental findings came from theoretical studies. Taken in concert this combination of theory and experiment served to confirm that the coupling between the excitons depends on the specifics of the calix[n]phyrin structure, not just its size.
关键词： Cyclic BODIPY,Boron,Exciton Coupling,Porphyrinoids,NIR Dye,Calix[n]phyrin
更新于2025-09-23 15:19:57
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Excitonically Coupled Cyclic BF2 Arrays of Calix[8]a?? and Calix[16]phyrin as Neara??IRa?? Chromophores
摘要： A pair of giant calix[n]phyrin derivatives namely calix[8]- (4) and calix[16]phyrin (5), involving two and four BF2 units, respectively, were prepared via the condensation of the bis-naphthobipyrrolylmethene-BF2 complex with pentafluorobenzaldehyde. Both systems and precursor 3 were fully characterized, including via single crystal X-ray diffraction analyses. Calix[n]phyrins 4 and 5 display extremely high extinction coefficients (3.67 and 4.82 105 M-1cm-1, respectively) in the near-IR region. This observation was taken as initial evidence for strong excitonic coupling within these cyclic multi-chromophoric systems. Detailed insights into the effect of excitonic coupling dynamics on the electronic structure and photophysical properties of the macrocycles came from theoretical studies. Taken in concert this combination of theory and experiment served to confirm that the coupling between the excitons depends on the specifics of the calix[n]phyrin structure, not just its size.
关键词： Cyclic BODIPY,Boron,Exciton Coupling,Porphyrinoids,NIR Dye,Calix[n]phyrin
更新于2025-09-23 15:19:57
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Heavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction
摘要： To test the tunability of charge transfer (CT)-based BODIPY photosensitizers in generating singlet oxygen (1D g), twelve meso-phenyl-BODIPY (donor-acceptor) type compounds have been synthesized and fully characterized, in which the phenyl moiety is modified with respective 0, 1, 2 and 3 methoxy groups to increase its electron-donating ability. The UV-Vis absorption spectra, fluorescence emission spectra, fluorescence quantum yield, fluorescence lifetime, excited triplet state formation, and singlet oxygen formation properties are measured. DFT quantum chemical computation is also carried out to explain the experiments. The occurrence of intra-molecular CT is confirmed by UV-Vis absorption, fluorescence properties and quantum chemical computation. The triplet excited state formation is evidenced by laser flash photolysis technique. The quantitative photosensitized singlet oxygen formation is demonstrated by DPBF (diphenylisobenzofuran) chemical trapping method. This type of BODIPY CT photosensitizers show good tunability in generating singlet oxygen (1D g). When the number of methoxy group on the donor is increased (so that CT is enhanced), the efficiency of singlet oxygen generation becomes higher from 0.070 to 0.30. When solvent polarity is increased (CT is also enhanced), the efficiency of singlet oxygen generation is also increased significantly. The increase in singlet oxygen generation is accompanied by the decrease in fluorescence quantum yield and fluorescence lifetime values. These facts show that a higher CT efficiency in a simple phenyl-BODIPY donor-acceptor conjugate can lead to significant higher quantum yield of singlet oxygen generation. These results are useful in designing novel CT-based heavy-atom-free photosensitizers for photodynamic therapy of tumor.
关键词： Charge transfer photosensitizer,singlet oxygen,BODIPY,photodynamic therapy
更新于2025-09-19 17:15:36