A water-stable boronate ester cage
Please always quote using this URN: urn:nbn:de:bvb:20-opus-361245
- 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 butThe 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.…
Author: | Philipp H. KirchnerORCiD, Louis SchrammORCiD, Svetlana IvanovaORCiD, Kazutaka ShoyamaORCiD, Frank WürthnerORCiD, Florian BeuerleORCiD |
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URN: | urn:nbn:de:bvb:20-opus-361245 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Language: | English |
Parent Title (English): | Journal of the American Chemical Society |
ISSN: | 0002-7863 |
Year of Completion: | 2024 |
Volume: | 146 |
Issue: | 8 |
Pagenumber: | 5305-5315 |
Source: | Journal of the American Chemical Society (2024) 146:8, 5305-5315. DOI: 10.1021/jacs.3c12002 |
DOI: | https://doi.org/10.1021/jacs.3c12002 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 547 Organische Chemie |
Tag: | absorption; boronate esters; hydrocarbons; materials; organic compounds; stability |
Release Date: | 2024/06/06 |
EU-Project number / Contract (GA) number: | 787937 |
OpenAIRE: | OpenAIRE |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |