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Title: Congegni Supramolecolari basati sul Threading di Calixareni
Authors: Talotta, Carmen
Guerra, Gaetano
Neri, Placido
Geraci, Corrada
Grassi, Alfonso
Keywords: Calixareni
Sistemi interbloccati
Issue Date: 1-Feb-2013
Publisher: Universita degli studi di Salerno
Abstract: Recently, Neri et al have introduced an efficient method to obtain endo-cavity complexation and through-the-annulus threading of large calixarenes exploiting the inducing effect of a weakly coordinating anion, tetrakis [3,5-bis (trifluoromethyl) phenyl]borate (TFPB-). In this PhD thesis this approach has been used for the synthesis of [2]rotaxanes, which showed an unprecedented inversion of the wheel orientation. Subsequently, it was extended to the synthesis of pseudo[3]rotaxane systems in which two calix[6]arene macrocycles are threaded by a bis(benzylalkylammonium) axle. Because of the three-dimensional nonsymmetrical nature of the calix[6]arene wheels, in these instances three sequence stereoisomers could be obtained, which were termed as headto- head (H,H), head-to-tail (H,T) and tail-to-tail (T,T). Taking advantage of these systems, it was possible to obtain the stereoprogrammed synthesis of the first examples of calixarene-based [3]rotaxane architectures. The base/acid treatment demonstrated that these systems act as molecular shuttles, which move on a nanometer scale level. The directionality of the threading and the observed high stereoselection have enabled the synthesis of directional calix[6]arene-based catenane. All these aspects represent interesting peculiar features of calixarene threading, which could be exploited for designing molecular machines with new properties or functions
Description: 2011 - 2012
Appears in Collections:Scienza e tecnologie per l’industria chimica, farmaceutica e alimentare

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