Prototropic tautomerism is one of the most important phenomena in organic chemistry. Tautomers are the chameleons of chemistry, capable of changing by a simple change of phase from an apparently established structure to another (not perhaps until then suspected), and then back again when the original conditions are restored, and of doing this in an instant: intriguing, disconcerting, perhaps at times exasperating. And a change in structure means changes in properties also. This creates a strong impact on the structure and performance of organic functional materials (according to various estimates between 60 and 80% of the commercial dyes are tautomeric), new hi-tech applications (OLEDs, laser dyes, irradiation protection, molecular electronics elements, etc.), bioactivity (~70% of the commercial drugs are tautomeric, large amount of the natural bioactive compounds as well), biochemistry and biomedicine.
The tautomerism is an interdisciplinary topic with very broad range of tools to be used – from advanced theoretical chemistry and cheminformatics, through variety of purely chemical experiments (organic synthesis, steady-state and time-dependent spectroscopies, scanning probe microscopy, crystallography; in gas phase, solution and solid state), to drug design and bioactivity testing. All this gives an excellent opportunity for training, providing a broad expertise in variety of methods and application.
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Proton Cranes ─ Tautomeric Systems for Intramolecular Cargo Delivery
Nature effectively employs the light-induced transfer of a proton for rapid interconversion between different electronic [...]
Tautomerism in 1-Pyridin-2-yl-1H-pyrazol-5-ols through the Prism of Molecular Switching: The Rare Case of OH/CH Switching upon Acidic Input
The tautomeric behavior of 1-(2-pyridinyl)-1H-pyrazol-5-ols has been investigated in solution using UV–vis and NMR spectroscopies [...]
Reversible Switching Based on Truly Intramolecular Long-Range Proton Transfer─Turning the Theoretical Concept into Experimental Reality
Herein, we demonstrate a working prototype of a conjugated proton crane, a reversible tautomeric switching [...]
