Issue 19, 2019

Shape induced sorting via rim-to-rim complementarity in the formation of pillar[5, 6]arene-based supramolecular organogels

Abstract

Two-component supramolecular organogels based on per-carboxylato- and per-amino pillar[6]arenes (2 and 4a–c) were prepared for the first time, and found to display very different characteristics as compared to those displayed by the corresponding pillar[5]arene derivatives (1 and 3a–c). Pillar[6]arenes derivatives, in contrast to pillar[5]arene derivatives, do not form organogels in alcoholic solutions and the formed gels in chlorinated solvents are, generally, more fragile. We analyzed the gelation ability of all the pairs between 1, 2, 3a–c and 4a–c, several three-component mixtures in 1 : 1 : 1 and 2 : 1 : 1 ratios, as well as four-component mixtures in ∼10 : 1 CDCl3 : DMSOd6 solutions. The obtained results clearly show that shape complementarity is an important determinant of gel formation in these supramolecular pillar[n]arene-based organogels. We also found that shape directed molecular sorting occurs in the gelation process of these two-component supramolecular organogels.

Graphical abstract: Shape induced sorting via rim-to-rim complementarity in the formation of pillar[5, 6]arene-based supramolecular organogels

Supplementary files

Article information

Article type
Research Article
Submitted
03 Jun 2019
Accepted
07 Aug 2019
First published
08 Aug 2019

Org. Chem. Front., 2019,6, 3348-3354

Shape induced sorting via rim-to-rim complementarity in the formation of pillar[5, 6]arene-based supramolecular organogels

D. Kaizerman-Kane, M. Hadar, E. Granot, F. Patolsky, Y. Zafrani and Y. Cohen, Org. Chem. Front., 2019, 6, 3348 DOI: 10.1039/C9QO00717B

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