Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties
| Authors | |
|---|---|
| Year of publication | 2021 |
| Type | Article in Periodical |
| Magazine / Source | European Journal of Organic Chemistry |
| MU Faculty or unit | |
| Citation | |
| web | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100705 |
| Doi | https://doi.org/10.1002/ejoc.202100705 |
| Keywords | Cucurbiturils; Host-guest complexes; Macrocycles; Monofunctionalization; Self-assembly |
| Description | Monofunctionalization of cucurbiturils is essential for transferring these potent supramolecular macrocyclic hosts into real-world application. Here, we present the synthesis of cucurbit[6]urils 1 and 2 in which one methylene bridge is modified by a single substituent containing a nitro or an ammonium group. We investigated host-guest properties in water and 0.2 M NaCl using H-1 NMR and isothermal titration calorimetry, particularly for 2. The macrocycle 2 self-associated into dimeric aggregates in pure water, but readily disassembled in the presence of NaCl or organic cations. Cucurbit[7]uril was able to encapsulate the ammonium substituent of 2 inside its cavity resulting in a complex of 1 : 1 stoichiometry with an association constant of 3.1x10(5) M-1. The presented host-guest properties together with further possible derivatization showcase the potential of cucurbiturils modified in the methylene position such as 1 and 2 for the development of advanced supramolecular systems. |
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