Abstract
Cucurbiturils are popular macrocyclic receptors that bind complementary guest molecules with high affinity in aqueous environments. They are recognized for their ability to selectively bind positively charged guest molecules, including ionizable ammonium cations which frequently display much higher affinity than their neutral counterparts. This selectivity for the protonated species is translated into an increase in the basicity of encapsulated guests (i. e. into complexation-induced positive pKa shifts). However, despite being very rare, negative pKa shifts can be observed for specific guests. Following a previous work from our group reporting slightly negative pKa shifts for flavylium and chalcone dyes featuring N-diethylamino substituents (ΔpKa=− 0.2), herein we report a systematic study on the complexation of N-dialkylaminochalcones with CB7. The results show that the pKa shifts of these host-guest complexes can be rationally tuned by the nature of the N-dialkylamino groups and as well by target substitutions on the skeleton of the dye, allowing the design of a CB7 1 : 1 host-guest complex with a ΔpKa=− 0.6.
Original language | English |
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Article number | e202300143 |
Number of pages | 10 |
Journal | Israel Journal of Chemistry |
Volume | 64 |
Issue number | 6-7 |
Early online date | 9 Jan 2024 |
DOIs | |
Publication status | Published - Jul 2024 |
Keywords
- Cavitands
- cucurbiturils
- host-guest systems
- pK shifts
- trans-chalcones