Related Experiment Video
Updated: Feb 6, 2026

Denaturing Urea Polyacrylamide Gel Electrophoresis Urea PAGE
Published on: October 29, 2009
Reversible gel-sol photoswitching with an overcrowded alkene-based bis-urea supergelator
Sander J Wezenberg1, Christelle M Croisetu1, Marc C A Stuart1,2
1Stratingh Institute for Chemistry , University of Groningen , Nijenborgh 4 , 9747 AG , Groningen , The Netherlands . Email: s.j.wezenberg@rug.nl ;
Abstract:
A new type of low-molecular-weight gelator (LMWG), i.e. overcrowded alkene-based bis-ureas, can be switched effectively between cis and trans isomers using light as demonstrated by 1H NMR and UV-Vis spectroscopy. Gelation studies reveal that one of the synthesized trans compounds forms stable gels in aromatic hydrocarbon solvents down to a critical concentration of 0.4 mg mL-1. Transmission electron microscopy (TEM) shows that this gel consists of an entangled fibrous network. For the trans isomer of this LMWG intermolecular urea hydrogen bonding is observed in the solid state, whereas density functional theory (DFT) geometry optimization of the cis isomer indicates the possible formation of an intramolecular hydrogen bond. Irradiation of the gel triggers trans-to-cis isomerization and consequently, a gel-sol phase transition. This process can be fully reversed by altering the irradiation wavelength.
Related Concept Videos
Urea Cycle
Nomenclature of Alkenes
As per the IUPAC rules, the longest carbon chain containing the maximum number of double bonds is identified as the parent chain and is numbered such that the doubly bonded carbon atoms receive the lowest possible numbers. The location of the double bond is indicated by the number of its first carbon atom. In branched...
Isomerism in Alkenes
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Structure and Bonding of Alkenes
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is...
Formation of Halohydrin from Alkenes

