Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F21%3A00119375" target="_blank" >RIV/00216224:14310/21:00119375 - isvavai.cz</a>
Result on the web
<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100705" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100705</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.202100705" target="_blank" >10.1002/ejoc.202100705</a>

Result language
angličtina
Original language name
Cucurbiturils Monofunctionalized on the Methylene Bridge and Their Host-Guest Properties
Original language 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.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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