Synthesis and Binding Properties of Monohydroxycucurbit[7]uril: A Key Derivative for the Functionalization of Cucurbituril Hosts
| Autor: | Angel E. Kaifer, Jing He, Mehdi Rashvand Avei, Andrea Peralta, Tao Li, Nan Dong, Mingfang Ma |
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| Rok vydání: | 2018 |
| Předmět: |
Aqueous solution
010405 organic chemistry Organic Chemistry Binding properties 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Computational chemistry Cucurbituril Yield (chemistry) Surface modification Chemical stability Derivative (chemistry) Binding affinities |
| Zdroj: | The Journal of Organic Chemistry. 83:5467-5473 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | We present a simple, direct method to prepare monohydroxylated cucurbit[7]uril (CB7-OH) through the direct oxidation of its precursor host, cucurbit[7]uril (CB7). Although the conversion takes place in low yield (14%), the isolation of CB7-OH from the reaction mixture is straightforward, and the unreacted CB7 can be easily recovered. ITC measurements with several selected guests confirmed that CB7-OH binds all of them in aqueous solution with similar, albeit slightly lower, binding affinities than those observed with the unmodified CB7 host. ESI mass spectrometric competition experiments are consistent with the ITC measurements. A variety of spectroscopic and voltammetric measurements also verify that the CB7-OH complexes exhibit properties essentially identical to those of the CB7 complexes. DFT computational data also confirm the similar thermodynamic stabilities and structures of the CB7-OH and CB7 inclusion complexes. Finally, the high thermodynamic stability of the CB7-OH complexes was used to improve on the extraction efficiency of stir bar sorptive extraction methods after suitable modification of the active coating with CB7-OH. |
| Databáze: | OpenAIRE |
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