2021
DOI: 10.1039/d1cc00240f
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Stuffed pumpkins: mechanochemical synthesis of host–guest complexes with cucurbit[7]uril

Abstract: Mechanochemical synthesis represents a new path towards unique types of cucurbit[n]uril/guest inclusion complexes that are not accessible due to limited solubility of the individual components.

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Cited by 16 publications
(14 citation statements)
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“…To better understand the interaction of guests 1 and 9 with cycHC[8] and cycHC[6], we investigated complex formation using 13 C ssNMR spectroscopy ( Figure 5C and Supplementary Materials S52–56 ). Recently, complex formation via mechanochemical agitation of cucurbit[7]uril was followed by ssNMR ( Dračínský et al, 2021 ). Powders obtained by liquid-assisted grinding of cycHC[ n ] with the guest in the presence of water served as the model for binding during the extraction process at the solute–solid interphase.…”
Section: Resultsmentioning
confidence: 99%
“…To better understand the interaction of guests 1 and 9 with cycHC[8] and cycHC[6], we investigated complex formation using 13 C ssNMR spectroscopy ( Figure 5C and Supplementary Materials S52–56 ). Recently, complex formation via mechanochemical agitation of cucurbit[7]uril was followed by ssNMR ( Dračínský et al, 2021 ). Powders obtained by liquid-assisted grinding of cycHC[ n ] with the guest in the presence of water served as the model for binding during the extraction process at the solute–solid interphase.…”
Section: Resultsmentioning
confidence: 99%
“…We decided to fill this gap by taking inspiration from the direct halogenations of parent cubane , and utilizing our extensive experience with chlorination reactions of strained bicyclo[1.1.1]pentane cages. , Our motivation was a desire to prepare and determine structural and physical properties of these unknown structures in order to use them as unique building blocks in our ongoing research focused on the study of (dipolar) rotors in the solid state. Herein, we report the synthesis of mono- 1 and all four possible dichlorinated cubane-1,4-dicarboxylates ( (+)-2a , (−)-2a , 2b , and 2c ), the electronic circular dichroism (ECD) spectra and optical rotation of both enantiomers of 2a , the crystal structures of these five compounds, the relative strain energies of newly synthesized structures as well as of hypothetical hexahalogenated diacids ( 6F , 6Cl , 6Br , and 6I ), and acidity constants for the newly prepared diacids (Chart ). The formation of individual dichlorinated isomers was rationalized by density functional theory (DFT) calculations.…”
Section: Introductionmentioning
confidence: 99%
“…The mechanochromic materials have widely been investigated in the literature. 13,14 It has been demonstrated that borondipyrromethylene (BODIPY) derivatives possess J-aggregation forming microcrystals 15 and are rendered with unusual high-contrast mechano-hypsochromism. In addition, the photoinduced proton transfer in an indolium derivative of photoacid to azobenzenes/phenolsulfonphthalein dye has been explored for applications in light-responsive rewritable papers.…”
Section: Introductionmentioning
confidence: 99%