The hexameric capsule-like structure of resorcinarene assembly was elucidated in 1997, which has been accepted as an indisputable structure formed in any apolar solvents over the past couple of decades. This paper presents the solvent dependence in the aggregation number (Nagg) of the C-undecylresorcinarene capsule and their micelle-like behavior in apolar solvents, whose structures were characterized with small angle X-ray scattering and analytical ultracentrifugation methods. The resorcinarene forms octameric structures in toluene, which demonstrated the temperature dependent morphological transition from spherical to cylindrical. This could reasonably be understood by packing parameter theory used in predicting micellar structures. Further, we determined the Nagg in toluene, chloroform, and mixture solvent of toluene/cyclohexane (vol/vol, 2/8) to be 8, 6, and 4, respectively. Interestingly, they showed perfect monodispersity in the Nagg. The aggregation behavior demonstrating monodispersity in the Nagg whose values are consistent with vertex or face number of regular polyhedral structures (i.e., Platonic solids) is known as that of Platonic micelles, suggesting that the resorcinarene capsules are the first example of Platonic “reverse” micelles.

Rediscovering micelle-like behavior of resorcinarene capsules and their unique aggregation number corresponding to Platonic structures

2019 Fall National Meeting

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