Coassembly behavior of the double hydrophilic block copolymer poly(4-hydroxystyrene)-block-poly(ethylene oxide) (PHOS-PEO) with three amphiphilic phenylboronic acids (PBA) differing in hydrophobicity, 4-dodecyloxyphenylboronic acid (C12), 4-octyloxyphenylboronic acid (C8), and 4-isobutoxyphenylboronic acid (i-Bu) was studied in alkaline aqueous solutions and in mixtures of NaOHaq/THF by spin-echo (1)H NMR spectroscopy, dynamic and electrophoretic light scattering, and SAXS. The study reveals that only the coassembly of C12 with PHOS-PEO provides spherical nanoparticles with intermixed PHOS and PEO blocks, containing densely packed C12 micelles. NMR measurements have shown that spatial proximity of PHOS-PEO and C12 leads to the formation of ester bonds between -OH of PHOS block and hydroxyl groups of -B(OH)2. Due to the presence of PBA moieties, the release of compounds with 1,2- or 1,3-dihydroxy groups loaded in the coassembled PHOS-PEO/PBA nanoparticles by covalent binding to PBA can be triggered by addition of a surplus of glucose that bind to PBA competitively. The latter feature has been confirmed by fluorescence measurements using Alizarin Red as a model compound. Nanoparticles were proved to exhibit swelling in response to glucose as detected by light scattering.

Department of Physical and Macromolecular Chemistry Faculty of Science Charles University Prague Hlavova 2030 128 40 Prague 2 Czech Republic

Department of Physical and Macromolecular Chemistry Faculty of Science Charles University Prague Hlavova 2030 128 40 Prague 2 Czech Republic Department of Physical Chemistry Faculty of Chemistry Warsaw University of Technology Noakowskiego 3 00664 Warsaw Poland

Department of Physical Chemistry Faculty of Chemistry Warsaw University of Technology Noakowskiego 3 00664 Warsaw Poland

Institute of Cellular Biology and Pathology 1st Faculty of Medicine Charles University Prague Albertov 4 128 01 Prague 2 Czech Republic

Theoretical and Physical Chemistry Institute National Hellenic Research Foundation 48 Vassileos Constantinou Avenue 11635 Athens Greece

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