Facile Purification of Rare Cucurbiturils by Affinity Chromatography

Abstract

A practical method for the separation and purification of cucurbituril (CB) hexamers was developed on the basis of affinity chromatography using aminopentylaminomethylated polystyrene beads. This recyclable resin, which can be used repeatedly, facilitates the general preparation of cucurbituril derivatives and compensates for the usually moderate yields and mixed products that characterize the acid-catalyzed synthesis of CB derivatives. This technique allows convenient, rapid isolation of rare substituted cucurbiturils, including hexacyclohexanocucurbit[6]uril and dodecamethylcucurbit[6]uril. [reaction: see text]

The Cucurbit[n]uril Family

“…[96] Keinan and coworkers recently reported a novel pentanediamine-derivatized polystyrene resin that allowed the isolation of Me 12 CB [6]. [259] Similarly, Kim and co-workers were able to isolate Cy 5 CB [5] (16 %) and Cy 6 CB[6] (2 %) by the cyclization of 1 e. [253] The distinguishing feature of Cy 5 CB [5] and 4 + , Na + , Cu 2+ , and choline). Nakamura and co-workers demonstrated that mixtures of 1 a and 1 c gave a CB [6] derivative containing a single diphenylglycoluril unit (Ph 2 CB- [1,5]) in a remarkable 30 % yield.…”

Chlorine Anion Encapsulation by Molecular Capsules Based on Cucurbit[5]uril and Decamethylcucurbit[5]uril

“…Figure 1) [14][15][16][17]. Recently some efforts have been made to introduce substitution in order to achieve ready solubility in both aqueous systems and common organic solvents, and a number of fully and partially substituted Q[n]s have been reported [18][19][20][21][22][23]. Decamethylcucurbit [5]uril (Me 10 Q [5]) was the first fully substituted Q[n] discovered in 1992 by Stoddart and co-workers [19].…”

Cucurbiturilas

“…Feng e seu grupo também desenvolveram uma metodologia de fixação de CBs em resinas poliméricas para a confecção de colunas cromatográficas com aplicações em química analítica 28 . Outras metodologias foram desenvolvidas com fins analíticos e para a purificação de compostos, dentre os quais os próprios cucurbitandos 39,180,181 .…”