Journal Article

PUBDB-2024-06619

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png A Water-Stable Boronate Ester Cage

Kirchner, P. H. ; Schramm, L. ; Ivanova, S. ; Shoyama, K.Extern* ; Wuerthner, F.Extern* ; Beuerle, F. (Corresponding author)Extern*

2024
ACS Publications Washington, DC

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Please use a persistent id in citations: doi:10.1021/jacs.3c12002  doi:10.3204/PUBDB-2024-06619

Abstract: 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.

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Contributing Institute(s):

1. DOOR-User (DOOR ; HAS-User)

Research Program(s):

1. 6G3 - PETRA III (DESY) (POF4-6G3) (POF4-6G3)
2. DFG project G:(GEPRIS)364877405 - Modulare Synthese von organischen Käfigen durch dynamisch-kovalente Chemie (364877405) (364877405)
3. SUPRAWOC - Supramolecular Architectures for Ruthenium Water Oxidation Catalysis (787937) (787937)

Experiment(s):

1. PETRA Beamline P11 (PETRA III)

Appears in the scientific report 2024

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