The selective recognition of caffeine in water among structurally related xanthines and purine or pyrimidine bases was achieved by a simple tweezer-shaped receptor featuring sulfonate hydrosolubilizing groups. The remarkable affinity for caffeine, among the highest reported thus far in the literature and larger than that shown by adenosine receptors of all subtypes, stems from a synergistic combination of hydrogen bonding, CH−π, and π-stacking interactions.
A Sulfonated Tweezer-Shaped Receptor Selectively Recognizes Caffeine in Water / Francesconi O.; Ienco A.; Papi F.; Dolce M.; Catastini A.; Nativi C.; Roelens S.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - ELETTRONICO. - 87:(2022), pp. 2662-2667. [10.1021/acs.joc.1c02620]
A Sulfonated Tweezer-Shaped Receptor Selectively Recognizes Caffeine in Water
Francesconi O.
;Nativi C.;Roelens S.
2022
Abstract
The selective recognition of caffeine in water among structurally related xanthines and purine or pyrimidine bases was achieved by a simple tweezer-shaped receptor featuring sulfonate hydrosolubilizing groups. The remarkable affinity for caffeine, among the highest reported thus far in the literature and larger than that shown by adenosine receptors of all subtypes, stems from a synergistic combination of hydrogen bonding, CH−π, and π-stacking interactions.
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acs.joc.1c02620.pdf
Open Access dal 03/02/2023
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