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The “Magic Linker”: Highly Effective Gelation from Sterically Awkward Packing

Smith, James P.; Yufit, Dmitry S.; McCabe, James F.; Steed, Jonathan W.

The “Magic Linker”: Highly Effective Gelation from Sterically Awkward Packing Thumbnail


James P. Smith

James F. McCabe


Bis(urea)s based on the 4,4′-methylenebis(2,6-diethylphenylene) (4,4′-MDEP) spacer are highly effective low molecular weight gelators, and the first single crystal structure of a bis(urea) based on this spacer is reported. The structure is a conformational isomorph with eight crystallographically independent molecules (Z′ = 8) arranged in four tennis-ball type dimers with the 2,6-diethylphenylene units adopting five different conformations in the ratio 4:5:3:2:2. The awkward shape and conformational promiscuity arising from the orientations of the ethyl groups in this system is linked to its gelation behavior. A total of seven 4,4′-MDEP derivatives have been prepared, and six are versatile gelators, confirming the particularly effective nature of the MDEP spacer. Only the nitrophenyl derivative does not form gels, likely because of intramolecular CH···O hydrogen bonding arising from the electron-withdrawing nature of the nitro substituent and hence inhibition of the urea α-tape hydrogen-bonded motif.


Smith, J. P., Yufit, D. S., McCabe, J. F., & Steed, J. W. (2022). The “Magic Linker”: Highly Effective Gelation from Sterically Awkward Packing. Crystal Growth and Design, 22(3), 1914-1921.

Journal Article Type Article
Online Publication Date Feb 9, 2022
Publication Date Mar 2, 2022
Deposit Date Apr 27, 2022
Publicly Available Date Aug 17, 2022
Journal Crystal Growth and Design
Print ISSN 1528-7483
Electronic ISSN 1528-7505
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 22
Issue 3
Pages 1914-1921


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This article is distributed under the terms of the Creative Commons Attribution License (CC-BY 4.0), which permits any use, distribution and reproduction in any medium, provided the original author(s) and source are credited.

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