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Micellar Polyaromatic Capsules: Enhanced Emissive Properties through Shell‐Functionalization
Author(s) -
Kondo Kei,
Suzuki Akira,
Akita Munetaka,
Yoshizawa Michito
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403136
Subject(s) - surface modification , chemistry , anthracene , amphiphile , micelle , fluorescence , aqueous solution , photochemistry , polymer chemistry , combinatorial chemistry , polymer , organic chemistry , copolymer , physics , quantum mechanics
Abstract 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.