Rationalising Supramolecular Hydrogelation of Bis‐Urea‐Based Gelators through a Multiscale Approach

Ruben Van Lommel, Laurens A. J. Rutgeerts, Wim M. De Borggraeve, Frank De Proft, Mercedes Alonso

Onderzoeksoutput: Articlepeer review

7 Citaten (Scopus)
54 Downloads (Pure)

Samenvatting

The current approach to designing low‐molecular‐weight gelators relies on a laborious trial‐and‐error process, mainly because of the lack of an accurate description of the noncovalent interactions crucial for supramolecular gelation. In this work, we report a multiscale bottom‐up approach composed of several computational techniques to unravel the key interactions in a library of synthesized bis‐urea‐based gelators and rationalize their experimentally observed hydrogelation performance. In addition to density functional theory calculations and molecular dynamics, the noncovalent interaction index is applied as a tool to visualise and identify the different types of noncovalent interactions. Interestingly, as well as hydrogen bonds between urea moieties, hydrogen bonds between a urea moiety and a pyridine ring were shown to play a detrimental role in the early aggregation phase. These findings enabled us to explain the hydrogelation performance observed in a library of twelve bis‐urea derivatives, which were synthesized with 58–95 % yields. From this library, three compounds were discovered to effectively gel water, with the most efficient hydrogelator only requiring a concentration of 0.2 w/v%.
Originele taal-2English
Pagina's (van-tot)267-276
Aantal pagina's10
TijdschriftChemPlusChem
Volume85
Nummer van het tijdschrift2
Vroegere onlinedatum19 okt 2019
DOI's
StatusPublished - feb 2020

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Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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