a method for synthesizing partially substituted cucurbit[n]uril方法合成部分代替葫芦[n]uril.pdfVIP

Molecules 2003, 8, 74-84 molecules ISSN 1420-3049 A Method for Synthesizing Partially Substituted Cucurbit[n]uril Anthony I. Day*, Alan P. Arnold and Rodney J. Blanch School of Chemistry, University College (UNSW), Australian Defence Force Academy, Canberra ACT 2600, Australia Tel. (61)-2-6268-8089, Fax (61)-2-6268-6268 * Author to whom correspondence should be addressed; e-mail a.day@.au Abstract: A novel approach to cucurbituril synthesis is described where partial substitution is introduced into cucurbit[n]uril. The identification of homologues (and their substitution) in reaction mixtures is achieved by a combination of ESMS and the use of the molecular probes (guests) 1,4- dioxane and 1,9-octanediamine. A unique symmetrical hexamethylcucurbit[3,3]uril, the major product, was isolated and characterized. Keywords: Macrocycles, molecular binding, partially substituted. Introduction The cucurbit[n]uril, Q[n], are an interesting new family of molecular hosts [1] that are both chemically and thermally robust. They have limited solubility in aqueous solvents, or organic solvents such as formic acid, acetic acid [2], trifluoroacetic acid and trifluoroethanol [3]. For more than ten years decamethylcucurbit[5]uril stood as the only fully substituted cucurbituril [4]. Recently the fully substituted cyclohexanocucurbit[n]uril, Cy Q[n], where n = 5 and 6, have been reported and these have some organic solvent solubility [5]. While n this latest report is encouraging for the possible achievement of other fully substituted cucurbiturils, the limiting factor