A Water-Stable Boronate Ester Cage.

Autor: Kirchner PH; Institut für Organische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg 97074, Germany.; Center for Nanosystems Chemistry (CNC), Julius-Maximilians-Universität Würzburg, Theodor-Boveri-Weg, Würzburg 97074, Germany., Schramm L; Institut für Organische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg 97074, Germany.; Center for Nanosystems Chemistry (CNC), Julius-Maximilians-Universität Würzburg, Theodor-Boveri-Weg, Würzburg 97074, Germany., Ivanova S; Institut für Organische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg 97074, Germany.; Center for Nanosystems Chemistry (CNC), Julius-Maximilians-Universität Würzburg, Theodor-Boveri-Weg, Würzburg 97074, Germany., Shoyama K; Institut für Organische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg 97074, Germany.; Center for Nanosystems Chemistry (CNC), Julius-Maximilians-Universität Würzburg, Theodor-Boveri-Weg, Würzburg 97074, Germany., Würthner F; Institut für Organische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg 97074, Germany.; Center for Nanosystems Chemistry (CNC), Julius-Maximilians-Universität Würzburg, Theodor-Boveri-Weg, Würzburg 97074, Germany., Beuerle F; Institut für Organische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg 97074, Germany.; Center for Nanosystems Chemistry (CNC), Julius-Maximilians-Universität Würzburg, Theodor-Boveri-Weg, Würzburg 97074, Germany.; Institut für Organische Chemie, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, Tübingen 72076, Germany.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2024 Feb 28; Vol. 146 (8), pp. 5305-5315. Date of Electronic Publication: 2024 Feb 07.
DOI: 10.1021/jacs.3c12002
Abstrakt: 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.
Databáze: MEDLINE
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