A5083335574- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Photochromic and Fluorescence Chemistry
- Luminescence and Fluorescent Materials
- Porphyrin and Phthalocyanine Chemistry
- Molecular Sensors and Ion Detection
- Nonlinear Optical Materials Studies
- Oxidative Organic Chemistry Reactions
- Photochemistry and Electron Transfer Studies
- Crystallography and molecular interactions
- Nonlinear Optical Materials Research
- Radical Photochemical Reactions
- Photoreceptor and optogenetics research
- Synthesis and Properties of Aromatic Compounds
- Synthesis of Organic Compounds
- Nuclear Physics and Applications
- Nanoplatforms for cancer theranostics
- Polydiacetylene-based materials and applications
- Cancer Treatment and Pharmacology
- Multicomponent Synthesis of Heterocycles
- Molecular Junctions and Nanostructures
- Chemical Synthesis and Analysis
- Synthesis and pharmacology of benzodiazepine derivatives
- Synthesis and Characterization of Pyrroles
- Supramolecular Chemistry and Complexes
Institute of Organic Chemistry
2015-2024
Polish Academy of Sciences
2015-2024
University of Warsaw
2017-2021
National Veterinary Research Institute
2015
National Academy of Sciences of Ukraine
2004-2013
Institute of Organic Chemistry
2004-2013
A combined experimental and theoretical study of the two-photon absorption (2PA) properties a series quadrupolar molecules possessing highly electron-rich heterocyclic core, pyrrolo[3,2-b]pyrrole, is presented. In agreement with quantum-chemical calculations, large 2PA cross-section values, σ2PA ≈10(2) -10(3) GM (1 GM=10(50) cm(4) s photon(-1) ), are observed at wavelengths 650-700 nm, which correspond to allowed but one-photon forbidden transitions. The calculations also predict that...
Introducing moderate charge-transfer character into nitro-aromatics is a key to producing strong fluorescence.
A highly efficient procedure for the synthesis of bis-coumarins fused at pyranone ring has been developed. The electron-rich phenols reacted with esters coumarin-3-carboxylic acids, leading to substituted chromeno[3,4-c]chromene-6,7-diones. reaction is catalyzed by both Lewis acids and 4-dimethylaminopyridine. most probable mechanistic pathway involves acid or DMAP transesterification, followed intramolecular conjugate addition α,β-unsaturated subsequent oxidation initially formed...
Abstract Electron-deficient π-conjugated functional dyes lie at the heart of organic optoelectronics. Adding nitro groups to aromatic compounds usually quenches their fluorescence via inter-system crossing (ISC) or internal conversion (IC). While strong electronic coupling with ensures benefits from these electron-withdrawing substituents, it also leads quenching. Here, we demonstrate how such affects photophysics acceptor–donor–acceptor fluorescent dyes, nitrophenyl acceptors and a...
Abstract A set of new octupolar merocyanine chromophores was designed and synthesized. These compounds were prepared from the reaction 1,3,5‐triformyl‐2,4,6‐trihydroxybenzene with heterocyclic nucleophiles. Octupolar dyes formed exclusively in their open‐dye form. The one‐ two‐photon‐absorption spectra consist two bands: long‐wavelength band two‐photon absorption spectrum (a few hundreds GM above 1000 nm) matches well intense, long‐wavelength‐absorption that is located visible region linear...
Tetraarylpyrrolo[3,2-b]pyrroles (TAPPs) possessing [1,1′-biphenyl]-2-yl substituents attached to the pyrrolic nitrogen atoms undergo selective double dehydrogenative cyclization accompanied by twofold 1,2-aryl migration under oxidative aromatic coupling conditions. The structure of product rearrangement has been unambiguously confirmed X-ray crystallography, and reaction pathway is supported density functional theory (DFT) calculations. Six-membered ring formation (requiring aryl around...
As part of a strategy to identify good fluorescent probes based on two-photon excited fluorescence (TPEF), the sensor for sodium cation has been designed bearing rhodol chromophore linked with an aza-crown ether. An efficient synthetic route derivatives possessing five-membered heterocycles at position 9 and their precursors that contain xanthylium salt developed. The synthesis involves condensation salts vinamidinium moiety 9, phenylhydrazine as key step. To accomplish 1-aza-15-crown-5...
Esters of coumarin-3-carboxylic acids undergo addition to DBU and DBN leading the formation a 6-membered ring.
Linking pyrrole[3,2-<italic>b</italic>]pyrrole core with azulene moieties leads to dyes possessing strong visible light absorption, no emission, and a two-photon absorption spectrum.
Dipyrrolonaphthyridinedione appended with para - or meta -nitrophenyl substituents exhibits strong fluorescence from a 1 ππ* S state.
Abstract A series of dyes bearing polymethine chromophore units in boron dipyrromethene (BODIPY) α‐positions were prepared by condensation 3,5‐dimethyl with various hemicyanines. One or two methyl groups the starting material can react, yielding corresponding mono‐ and disubstituted derivatives. The deeply coloured monosubstituted belong to family merocyanine exhibit spectral properties chemical behaviour similar those meso ‐analogues. On other hand, show more complex absorption spectra...
Abstract Hyper‐Rayleigh scattering experiments and quantum chemical calculations are combined to investigate the second‐order nonlinear optical responses of a series three‐arm merocyanine derivatives. They exhibit an octupolar hyperpolarizability response with lower amplitude than crystal violet due extent photoinduced charge transfer reduced bond length alternation. Strong effects on measured close two‐photon absorption level clearly evidenced; for example, effective polarization ratio...
Hybridization of electron donors and acceptors provides routes to long-wavelength absorbing fluorescing dyes. Varying the coupling low-lying charge-transfer (CT) states with ground different locally excited profoundly affects photophysics such donor–acceptor conjugates. Herein, we hybridize an electron-deficient diketopyrrolopyrrole (DPP) moiety electron-rich pyrrolopyrrole (PP) that is symmetrically N-arylated 4-nitrophenyl substituents. The lowest Franck–Condon state located on DPP ring...
The fluorescence properties of two new families heterocycles possessing either a seven- or five-membered ring attached at the core molecule are entirely different in solution and solid state. Crystallization has effect inhibiting non-radiative excited-state deactivation pathways, operative for seven-membered compounds, thus leading to significant efficiency state, with quantum yields ranging from 0.10 0.36. Conversely, derivatives, which display notable emission solution, almost non-emissive...
Two strategies were shown to be efficient in the construction of corroles with appended coumarin units. Direct condensation formyl-coumarins dipyrromethanes leads a diverse range trans-A 2 B-corroles moderate yields. We showed that strategy consisting synthesis various hydroxycoumarins followed by nucleophilic aromatic substitution pentafluorobenzaldehyde and subsequent resulting coumarin-aldehyde is most general methodology for preparation such dyads. The second, more demanding but also...
The controlled hydrolysis of sulfone-rhodamines affords a series core-modified red-emitting rhodols, the fluorescence which is sensitive to solvent polarity. After equipping with PPh<sub>3</sub><sup>+</sup> group they selectively stain mitochondria.
Abstract A number of new BODIPY dyes with benzothiazolyl substituents have been synthesized that exhibit long‐wavelength absorption and act as strong fluorophores. The optical properties the were studied by using spectroscopic methods quantum‐chemical calculations. structural peculiarities obtained, in comparison to their analogues, X‐ray analysis.
Two strongly polarized dipolar chromophores possessing a cyclic tertiary amino group at one terminus of the molecule and CN opposite were designed synthesized. Their rigid skeleton contains rarely studied pyrrolo[2,3-b]quinoxaline ring system. The photophysical properties these regioisomeric dyes different owing to differing π conjugation between electron-donor moiety. These molecules showed very intense emission, strong solvatofluorochromism, sufficient two-photon brightness for bioimaging....
This communication describes the photophysical behavior of three analogs cyclophane bearing dipyrrolonaphthyridinedione (DPND) core. In these molecules, intersystem crossing (ISC) can be successfully induced by distinct changes in deviation from planarity within DPND core, allowing at same time emission maximum to shift green red region visible spectrum without any synthetic modifications chromophore structure. finding may build foundation for a new paradigm inducing ISC-type transitions...
The lactone carbonyl group of coumarin derivatives has been shown to participate in intramolecular Knoevenagel condensations, enabling the unprecedented direct transformation coumarins into rhodols. resulting rhodols, possessing two ester groups, have very intense orange-red fluorescence.
Strong fluorescence is a general feature of dipyrrolonaphthyridinediones bearing two nitrophenyl substituents. Methyl groups simultaneously being weakly electron-donating and inducing steric hindrance appear to be key structural parameter that allows for significant emission enhancement, whereas Et2N cause quenching. The magnitude two-photon absorption increases if 4-nitrophenyl substituents are present while the contribution detrimental.