Macrocyclic Bridgehead Fluorophores, Pyrrolyl-diazabicyclo[8.3.1]tetradecadienones, with Giant Stokes Shifts.

A previously unknown class of fluorophores was discovered, which represents 14-membered bridgehead heterocycles, pyrrolyl-diazabicyclo[8.3.1]tetradecadienones, herein referred to as PY-14-ONEs.

Contributing to Biochemistry and Optoelectronics: Pyrrolo[1',2':2,3]imidazo[1,5-]indoles and Cyclohepta[4,5]pyrrolo[1,2-]pyrrolo[1,2-]imidazoles via [3+2] Annulation of Acylethynylcycloalka[]pyrroles with Δ-Pyrrolines.

Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[]indolyl moieties, acylethynylcycloalka[]pyrroles, are readily annulated with Δ-pyrrolines (MeCN/THF, 70 °C, 8 h) to afford a series of novel pyrrolo[1',2':2,3]imidazo[1,5-]indoles and cyclohepta[4,5]pyrrolo[1,2-]pyrrolo[1,2-]imidazoles functionalized with an acylethenyl group in up to an 81% yield. This original synthetic approach contributes to the arsenal of chemical methods promoting drug discovery. Photophysical studies show that some of the synthesized compounds, e.

Application of -CF-Fluorophore BODIPY with Phenyl and Pyrazolyl Substituents for Lifetime Visualization of Lysosomes.

A bright far-red emitting unsymmetrical -CF-BODIPY fluorescent dye with phenyl and pyrazolyl substituents was synthesized by condensation of trifluoropyrrolylethanol with pyrazolyl-pyrrole, with subsequent oxidation and complexation of the formed dipyrromethane. This BODIPY dye exhibits optical absorption at λ ≈ 610-620 nm and emission at λ ≈ 640-650 nm. The BODIPY was studied on Ehrlich carcinoma cells as a lysosome-specific fluorescent dye that allows intravital staining of cell structures with subsequent real-time monitoring of changes occurring in the cells.

Theoretical Investigation of Carbon Dioxide Adsorption on Li-Decorated Nanoflakes.

Recently, the capture of carbon dioxide, the primary greenhouse gas, has attracted particular interest from researchers worldwide. In the present work, several theoretical methods have been used to study adsorption of CO molecules on Li-decorated coronene (Li@coronene). It has been established that Li can be strongly anchored on coronene, and then a physical adsorption of CO will occur in the vicinity of this cation.

Effect of methyl substituents on the electronic transitions in simple meso-aniline-BODIPY based dyes: RI-CC2 and TD-CAM-B3LYP computational investigation.

The S→S, i=1-5 electronic transitions of four 8-(4-aniline)-BODIPY and four 8-(N,N-dimethyl)-BODIPY dyes, differ by number and position of methyl substituents in the BODIPY frame, were investigated theoretically using ab initio the coupled cluster doubles (CC2) and TD-CAM-B3LYP methods. Methyl substituents in the BODIPY frame and the aniline fragment at the meso position disturb energy of local excitations S→S, S→S, and S→S weakly in comparison with the fully unsubstituted BODIPY molecule. These transitions in experimental spectra form the most long-wave absorption bands at ca.

General route to symmetric and asymmetric meso-CF3-3(5)-aryl(hetaryl)- and 3,5-diaryl(dihetaryl)-BODIPY dyes.

A general efficient route to hitherto inaccessible symmetric and asymmetric meso-CF(3)-BODIPY dyes has been developed. The key stages include the reduction of available 2-trifluoroacetylpyrroles to the corresponding alcohols which are further condensed with pyrroles. The method allows the BODIPY with 3(5)aryl(hetaryl) and 3,5-diaryl(hetaryl) substituents to be readily assembled.

Synthesis and optical properties of 2-(benzo[b]thiophene-3-yl)pyrroles and a new BODIPY fluorophore (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene).

2-(Benzo[b]thiophene-3-yl)-1-vinylpyrrole has been synthesized directly from 3-acetylbenzo[b]thiophene oxime and acetylene (flow system, KOH-DMSO, 120 degrees C, 5 h) in 68% yield. Devinylation of the synthesized pyrrole (Hg(OAc)(2), NaBH(4), 50 degrees C) led to the corresponding 2-(benzo[b]thiophene-3-yl)pyrrole in 63% yield. Trifluoroacetylation of both the pyrroles with trifluoroacetic anhydride (80 degrees C, 1 h) gave the corresponding 5-trifluoroacetyl pyrroles in 97% and 76% yields, respectively.