5390 J. Org. Chem. 2009, 74, 5390–5394 Published on Web 06/24/2009 DOI: 10.1021/jo900894q r 2009 American Chemical Society pubs.acs.org/joc Chloroalkane Gel Formations by Tris-urea Low Molecular Weight Gelator under Various Conditions Masamichi Yamanaka* and Hiromitsu Fujii Department of Chemistry, Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan smyaman@ipc.shizuoka.ac.jp Received April 30, 2009 C 3 -symmetrical tris-urea low molecular weight gelator 1 was synthesized in three steps from phloroglucin. The gelation ability of 1 in four chloroalkanes, i.e., CH 2 Cl 2 , CHCl 3 , 1,1,2-trichloro- ethane, and 1,1,2,2-tetrachloroethane, was investigated under various conditions. Thermal treatment was effective in gelating 1,1,2-trichloroethane. In the presence of equimolar 1 and CuBr 2 , 1,1, 2-trichloroethane and 1,1,2,2-tetrachloroethane formed gels. Mixtures of 1 and CHCl 3 or 1,1,2, 2-tetrachloroethane gave gels after ultrasound irradiation. CH 2 Cl 2 changed into a gel in the presence of equimolar 1 and BiCl 3 after sonication. Spherical particles with rough surfaces were found by SEM observation of CHCl 3 gel prepared from ultrasound irradiation of 1 and Y(NO 3 ) 3 . Introduction Regulated assembly of a low molecular weight compound builds up a supramolecular gel. Many low molecular weight gelators (LMWGs) have been reported. 1-9 The ability to use several stimuli for the sol-gel phase transition based on the rational design of LMWGs is a remarkable advantage of supramolecular gels. 10-14 These reversible conversions of rheol- ogy have potential as future materials with wide application in *To whom correspondence should be addressed. Phone: (þ81) 54-238- 4936. Fax: (þ81) 54-237-3384. (1) (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133–3159. (b) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237–1247. (c) van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263–2266. (d) Estroff, L. 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