Calix[6]arene-Based [3]Rotaxanes as Prototypes for the Template Synthesis of Molecular Capsules

被引:2
作者
Cester Bonati, Federica [1 ]
Bazzoni, Margherita [1 ]
Baccini, Caterina [1 ]
Zanichelli, Valeria [1 ]
Orlandini, Guido [1 ]
Arduini, Arturo [1 ]
Cera, Gianpiero [1 ]
Secchi, Andrea [1 ]
机构
[1] Univ Parma, Dipartimento Sci Chim Vita & Sostenibil Ambientale, Parco Area Sci 17-A, I-43124 Parma, Italy
关键词
calix[6]arenes; 3]rotaxanes; NMR Spectroscopy; template synthesis; viologens; WHEEL; PSEUDOROTAXANE; RECOGNITION; ASSEMBLIES; CAGES;
D O I
10.3390/molecules28020595
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In this work, the ability of several bis-viologen axles to thread a series of heteroditopic tris(N-phenylureido)calix[6]arene wheels to give interwoven supramolecular complexes to the [3]pseudorotaxane type was studied. The unidirectionality of the threading process inside these nonsymmetric wheels allows the formation of highly preorganised [3]pseudorotaxane and [3]rotaxane species in which the macrocycles phenylureido moieties, functionalised with either ester, carboxylic, or hydroxymethyl groups, are facing each other. As verified by NMR and semiempirical computational studies, these latter compounds possess the correct spatial arrangement of their subcomponents, which could lead, in principle, upon proper bridging reaction, to the realisation of upper-to-upper molecular capsules that are based on calix[6]arene derivatives.
引用
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页数:18
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