40047-93-6Relevant articles and documents
Ferrocenyl aza-dipyrromethene and aza-BODIPY: Synthesis and properties
Sharma, Rekha,Maragani, Ramesh,Misra, Rajneesh
, p. 8 - 14 (2016)
A series of ferrocenyl substituted tetraphenylazadipyrromethane and Aza-BODIPY were designed and synthesized by the Pd-catalyzed Sonogashira cross-coupling reaction. The effect of the pyrrolic substituents on photophysical and electrochemical properties w
Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics
Etheridge, Forrest S.,Fernando, Roshan J.,Peji?, Sandra,Zeller, Matthias,Sauvé, Geneviève
, p. 1925 - 1938 (2016)
Homoleptic zinc(II) complexes of di(phenylacetylene)azadipyrromethene (e.g., Zn(WS3)2) are potential non-fullerene electron acceptors for organic photovoltaics. To tune their properties, fluorination of Zn(WS3)2 at various positions was investigated. Three fluorinated azadipyrromethene-based ligands were synthesized with fluorine at the para-position of the proximal and distal phenyl groups, and at the pyrrolic phenylacetylene moieties. Additionally, a CF3 moiety was added to the pyrrolic phenyl positions to study the effects of a stronger electron withdrawing unit at that position. The four ligands were chelated with zinc(II) and BF2+ and the optical and electrochemical properties were studied. Fluorination had little effect on the optical properties of both the zinc(II) and BF2+ complexes, with λmax in solution around 755 nm and 785 nm, and high molar absorptivities of 100 × 103 M-1cm-1 and 50 × 103 M-1cm-1, respectively. Fluorination of Zn(WS3)2 raised the oxidation potentials by 0.04 V to 0.10 V, and the reduction potentials by 0.01 V to 0.10 V, depending on the position and type of substitution. The largest change was observed for fluorine substitution at the proximal phenyl groups and CF3 substitution at the pyrrolic phenylacetylene moieties. The later complexes are expected to be stronger electron acceptors than Zn(WS3)2, and may enable charge transfer from other conjugated polymer donors that have lower energy levels than poly(3-hexylthiophene) (P3HT).
Difluoroborates of phenyl-substituted aza-dipyrromethenes: Preparation, spectral properties, and stability in solution
Dudina,Berezin,Semeikin,Antina
, p. 2739 - 2742 (2015)
Boron(III) complexes with phenyl-substituted meso-aza-dipyrromethenes (one of them 4,4'-brominated) have been prepared. The bromination has resulted in weakening of the compound fluorescence by more than ten-fold. The studied complexes are stable for a lo
Aza-BODIPY based probe for photoacoustic imaging of ONOO? in vivo
Ma, Danghui,Hou, Shumin,Bae, Chaeeon,Pham, Thanh Chung,Lee, Songyi,Zhou, Xin
, p. 3886 - 3889 (2021/07/06)
The effective detecting ONOO? variations in vivo is of great importance to well understand the complex pathophysiological processes. We reported here a photoacoustic (PA) probe AZB-1 for imaging ONOO? in vivo. AZB-1 showed an origina
Deep-Red-Fluorescent Zinc Probe with a Membrane-Targeting Cholesterol Unit
Hong, Jayeon,Kim, Jin Ju,You, Youngmin,Yu, Seungyeon
, p. 11562 - 11576 (2020/09/09)
Organelle-targeting fluorescence probes are valuable because they can provide spatiotemporal information about the trafficking of analytes of interest. The spatiotemporal resolution can be improved by using low-energy emission signals because they are barely contaminated by autofluorescence noises. In this study, we designed and synthesized a deep-red-fluorescent zinc probe (JJ) with a membrane-targeting cholesterol unit. This zinc probe consists of a boron-azadipyrromethene (aza-BODIPY) fluorophore and a zinc receptor that is tethered to a tri(ethylene glycol)-cholesterol chain. In aqueous solutions buffered to pH 7.4, JJ exhibits weak fluorescence with a peak wavelength of 663 nm upon excitation at 622 nm. The addition of ZnCl2 elicits an approximately 5-fold enhancement of the fluorescence emission with a fluorescence dynamic range of 141000. Our electrochemical and picosecond transient photoluminescence investigations indicate that the fluorescence turn-on response is due to the zinc-induced abrogation of the formation of a nonemissive intramolecularly charge-separated species, which occurs with a driving force of 0.98 eV. The fluorescence zinc response was found to be fully reversible and to be unaffected by pH changes or the presence of biological metal ions. These properties are due to tight zinc binding with a dissociation constant of 4 pM. JJ was found to be nontoxic to HeLa cells up to submicromolar concentrations, which enables cellular imaging. Colocalization experiments were performed with organelle-specific stains and revealed that JJ is rapidly internalized into intracellular organelles, including lysosomes and endoplasmic reticula. Unexpectedly, probe internalization was found to permeabilize the cell membrane, which facilitates the influx of exogens such as zinc ions. Such permeabilization does not arise for a control probe without the tri(ethylene glycol)-cholesterol chain (JJC). Our results show that the membrane-targeting cholesterol unit can disrupt membrane integrity.
Photodynamic treatment of melanoma cells using aza-dipyrromethenes as photosensitizers
Biazzotto, Juliana C.,Castro, Kelly A. D. F.,Costa, Letícia D.,Da Silva, Roberto S.,Faustino, M. Amparo F.,Guieu, Samuel,Neves, Maria Da Gra?a P. M. S.,Tomé, Augusto C.
, p. 885 - 891 (2020/07/23)
In this study, we report for the first time the use of four aza-dipyrromethenes (ADPMs) as photosensitizers for cancer PDT. The synthesis and characterization of the ADPMs and their photodynamic action against B16F10 melanoma cells were assessed. ADPM 2 i
Synthesis, properties and reactivity of BCl2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold
Burke, Luke,Diaz-Rodriguez, Roberto M.,Robertson, Katherine N.,Thompson, Alison
, p. 2139 - 2147 (2020/03/27)
The synthesis and characterisation of the BCl2-chelated complexes of both archetypal aza-dipyrrin sub-Types are presented. A stepwise halogen exchange, leading to a mixed-halide Cl-B-F intermediate, is implicated in the conversion of F-Aza-BODIPYs to Cl-Aza-BODIPYs upon treatment with BCl3. The utility of the Cl-Aza-BODIPY scaffold to facilitate substitutions at boron is demonstrated under mild conditions through treatment with aryl Grignard reagents. Additionally, the lability of the B-Cl bond enables facile removal of the BCl2 group, i.e. deprotection of F-Aza-BODIPYs, under aqueous conditions. Three aza-dipyrrin HX salts were also synthesised and characterised. The pKa of the protonated aza-dipyrrin was determined to be 4, thereby providing insight regarding the storage and stability of such species.
Water-soluble PnO2 - PODIPY/PnO2 - azaPODIPY fluorescent dye and its preparation method
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Paragraph 0083; 0084; 0085, (2017/08/25)
The invention relates to a dye and a preparation method thereof. The fluorescent dye is a series of novel dye which takes PnO2-PODIPY/PnO2-azaPODIPY developed from dipyrrin/aza-dipyrromethene complexing PnO2 (Pn-P, As, Sb, Bi) as a parent nucleus, and the
Reaction between 4-Nitro-1,3-diarylbutan-1-ones and Ammonium Acetate in the Presence of Morpholine and Sulfur: An Efficient Synthesis of 2,4-Diarylpyrroles
Adib, Mehdi,Ayashi, Neda,Heidari, Fatemeh,Mirzaei, Peiman
, p. 1738 - 1742 (2016/07/06)
An efficient synthesis of 2,4-diarylpyrroles is described. Heating a mixture of a 4-nitro-1,3-diarylbutan-1-one and ammonium acetate in the presence of morpholine and sulfur afforded the corresponding 2,4-diarylpyrroles in excellent yields.
The effect of heavy atom to two photon absorption properties and intersystem crossing mechanism in aza-boron-dipyrromethene compounds
Karatay, Ahmet,Miser, M. Ceren,Cui, Xiaoneng,Kü?ük?z, Betül,Yilmaz, Halil,Sevin?, G?khan,Akhüseyin, Elif,Wu, Xueyan,Hayvali, Mustafa,Yaglioglu, H. Gul,Zhao, Jianzhang,Elmali, Ayhan
, p. 286 - 294 (2015/08/06)
Abstract New aza-boron-dipyrromethene compounds containing bromine atoms at various positions were designed and synthesized to enhance the triplet state population and two photon absorption properties for applications such as two-photon photodynamic therapy, triplet-triplet annihilation up-conversion. Steady state fluorescence and ultrafast pump probe spectroscopy techniques revealed that only 2, 6 positions of aza-boron-dipyrromethene core contribute to triplet state population significantly. Density function theory calculations showed that when bromine atoms introduced to 2, 6 position of aza-boron-dipyrromethene core, singlet and triplet energy levels get closer therefore probability of intersystem crossing increases. Z-scan experiments at 800 nm wavelengths revealed considerably large (610 GM) two photon absorption cross section value with respect to literature for compounds showing intersystem crossing mechanism. The efficient intersystem crossing and enhanced two-photon absorption properties make the investigated aza-boron-dipyrromethene compounds good candidates for two-photon photodynamic therapy application.
