Currently, the chemistry of organofluorine compounds is a leading and rapidly developing area of organic chemistry. Fluorine present in a molecule largely determines its specific chemical and biological properties. This thematic issue covers the trends of organofluorine chemistry that have been actively developed in Russia the last 15 – 20 years. The review describes nucleophilic substitution and heterocyclization reactions involving fluorinated arenes and quinones and skeletal cationoid rearrangements in the polyfluoroarene series. The transformations involving CF3-substituted carbocations and radical cations are considered. Heterocyclization and oxidative addition reactions of trifluoroacetamide derivatives and transformations of the organic moiety in polyfluorinated organoboranes and borates with retention of the carbon – boron bond are discussed. Particular attention is devoted to catalytic olefination using freons as an efficient synthetic route to fluorinated compounds. The application of unsymmetrical fluorine-containing N-heterocyclic carbene ligands as catalysts for olefin metathesis is demonstrated. A variety of classes of organofluorine compounds are considered, in particular, polyfluorinated arenes and 1,2-diaminobenzenes, 1-halo-2-trifluoroacetylacetylenes, α-fluoronitro compounds, fluorinated heterocycles, 2-hydrazinylidene-1,3-dicarbonyl derivatives, imines and silanes. The potential practical applications of organofluorine compounds in fundamental organic chemistry, materials science and biomedicine are outlined.
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Background:
Quinazolines, the important group of benzodiazines, are widely known in medicinal
chemistry due to their broad spectrum of biological activities. Notably, extensive research on the synthesis and
application of quinazoline derivatives for electronic devices, luminescent elements, photoelectric conversion
elements, and image sensors has been published recently.
Objective:
This review reports luminescent small molecules and chelate compounds including a quinazoline or
pyrimidine ring in their scaffold highlighting their applications related to photo- and electroluminescence.
Conclusion:
It is clear from the review of the topic that the incorporation of quinazoline and pyrimidine fragments
into π-extended conjugated systems is of great value for the creation of novel optoelectronic materials.
Polyhalogen derivatives represent the major starting materials for polysubstituted fluorescent quinazolines.
Electroluminescent properties of aryl(hetaryl)substituted quinazolines with π-extended conjugated systems
proved to be the most important. Incorporation of benzimidazole, carbazole, triphenylene or triphenylamine
fragments into quinazoline scaffold allows fabricating materials for organic light-emitting diodes, including
white OLEDs and highly efficient red phosphorescent organic light-emitting diodes. Moreover,
arylvinylsubstituted quinazolines are of great interest as potential structures for nonlinear optical materials and
for colorimetric pH sensors. Iridium complexes based on 2-aryl(thienyl) quinazoline or pyrimidine derivatives
represent high-efficiency phosphorescent materials for OLEDs. Pyrimidine push-pull systems are of considerable
importance as potential photosensitizers for dye-sensitized solar cells. Pyrimidine derivatives bearing
phenylacridine or phenylphenoxazine fragments at the positions 4 and 6 are capable to function as thermally
activated delayed fluorescence emitters.
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