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Functionalization of the polyaromatic shell of a micelle-like molecular capsule was accomplished by simple functionalization of the amphiphilic subunits composed of a bent bis-anthracene framework and two trimethylammonium groups. In aqueous solutions, functionalized subunits assemble spontaneously and quantitatively into spherical capsules providing anthracene shells with external diameters of 2-3 nm through hydrophobic and aromatic-aromatic interactions. The shape and size of the functionalized capsules remain similar to the original, but the emissive intensities increase significantly (up to 5-fold) by attaching cyano or phenylethynyl groups. Furthermore, the shell-functionalization drastically enhances the host-guest photophysical properties (up to 8-fold) in the cavities of the capsules, as estimated by emission intensities from the encapsulated fluorescent dyes. [ABSTRACT FROM AUTHOR]

Atroposelective formation: Selective formation of a molecular capsule was demonstrated from an amphiphilic cis‐atropisomer bearing three anthracene rings and four sulfonate groups through hydrophobic and aromatic–aromatic interactions. The dimeric capsule binds small guest molecules; the resultant host–guest complexes exhibit ground‐state charge‐transfer interactions accompanied by changes in host emission. [ABSTRACT FROM AUTHOR]