TY  - JOUR
A1  - Kirchner, Philipp H.
A1  - Schramm, Louis
A1  - Ivanova, Svetlana
A1  - Shoyama, Kazutaka
A1  - Würthner, Frank
A1  - Beuerle, Florian
T1  - A water-stable boronate ester cage
T2  - Journal of the American Chemical Society
N2  - The reversible condensation of catechols and boronic acids to boronate esters is a paradigm reaction in dynamic covalent chemistry. However, facile backward hydrolysis is detrimental for stability and has so far prevented applications for boronate-based materials. Here, we introduce cubic boronate ester cages 6 derived from hexahydroxy tribenzotriquinacenes and phenylene diboronic acids with ortho-t-butyl substituents. Due to steric shielding, dynamic exchange at the Lewis acidic boron sites is feasible only under acid or base catalysis but fully prevented at neutral conditions. For the first time, boronate ester cages 6 tolerate substantial amounts of water or alcohols both in solution and solid state. The unprecedented applicability of these materials under ambient and aqueous conditions is showcased by efficient encapsulation and on-demand release of β-carotene dyes and heterogeneous water oxidation catalysis after the encapsulation of ruthenium catalysts.
KW  - absorption
KW  - hydrocarbons
KW  - materials
KW  - organic compounds
KW  - stability
KW  - boronate esters
Y1  - 2024
UR  - https://opus.bibliothek.uni-wuerzburg.de/frontdoor/index/index/docId/36124
UR  - https://nbn-resolving.org/urn:nbn:de:bvb:20-opus-361245
SN  - 0002-7863
VL  - 146
IS  - 8
ER  -