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

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]are...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 19; pp. 3348 - 3354
Main Authors Kaizerman-Kane, Dana, Hadar, Maya, Granot, Eran, Patolsky, Fernando, Zafrani, Yossi, Cohen, Yoram
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.10.2019
Royal Society of Chemistry
Subjects
Aromatic compounds
Chemistry
Chemistry, Organic
Complementarity
Derivatives
Gelation
Gels
Organic chemistry
Physical Sciences
Science & Technology
GELS
MOLECULAR RECOGNITION
COMPLEXES
CUCURBITURIL
RELEASE
PEPTIDE
MULTIVALENCY
HYDROGEL
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Summary: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 similar to 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.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo00717b