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Anion-Responsive Fluorescent Supramolecular Gels

Picci, Giacomo; Mulvee, Matthew T.; Caltagirone, Claudia; Lippolis, Vito; Frontera, Antonio; Gomila, Rosa M.; Steed, Jonathan W.

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Giacomo Picci

Matthew T. Mulvee

Claudia Caltagirone

Vito Lippolis

Antonio Frontera

Rosa M. Gomila


Three novel bis-urea fluorescent low-molecular-weight gelators (LMWGs) based on the tetraethyl diphenylmethane spacer—namely, L1, L2, and L3, bearing indole, dansyl, and quinoline units as fluorogenic fragments, respectively, are able to form gel in different solvents. L2 and L3 gel in apolar solvents such as chlorobenzene and nitrobenzene. Gelator L1 is able to gel in the polar solvent mixture DMSO/H2O (H2O 15% v/v). This allowed the study of gel formation in the presence of anions as a third component. An interesting anion-dependent gel formation was observed with fluoride and benzoate inhibiting the gelation process and H2PO4−, thus causing a delay of 24 h in the gel formation. The interaction of L1 with the anions in solution was clarified by 1H-NMR titrations and the differences in the cooperativity of the two types of NH H-bond donor groups (one indole NH and two urea NHs) on L1 when binding BzO− or H2PO4− were taken into account to explain the inhibition of the gelation in the presence of BzO−. DFT calculations corroborate this hypothesis and, more importantly, demonstrate considering a trimeric model of the L1 gel that BzO− favours its disruption into monomers inhibiting the gel formation.


Picci, G., Mulvee, M. T., Caltagirone, C., Lippolis, V., Frontera, A., Gomila, R. M., & Steed, J. W. (2022). Anion-Responsive Fluorescent Supramolecular Gels. Molecules, 27(4), Article 1257.

Journal Article Type Article
Acceptance Date Feb 9, 2022
Online Publication Date Feb 13, 2022
Publication Date 2022
Deposit Date Feb 14, 2022
Publicly Available Date Feb 15, 2022
Journal Molecules
Publisher MDPI
Peer Reviewed Peer Reviewed
Volume 27
Issue 4
Article Number 1257


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