Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 35, Pages 10356-10360Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502983
Keywords
boronate esters; cages compounds; dynamic covalent chemistry; self-sorting; tribenzotriquinacenes
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Funding
- Collaborative Research Network Solar Technologies Go Hybrid of the Bavarian Ministry of Science, Research and the Arts
- Fonds der Chemischen Industrie
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The directional bonding approach is a powerful tool to rationally control both shape and stoichiometry of three-dimensional objects built from rigid building blocks under dynamic covalent conditions. Co-condensation of catechol-functionalized tribenzotriquinacene derivatives which have 90 degrees angles between the reactive sites and diboronic acids with bite angles of 60 degrees, 120 degrees, and 180 degrees, led to the efficient formation of, respectively, bipyramidal, tetrahedral, or cubic covalent organic cage compounds in a predictable manner. Investigations on the self-sorting of ternary mixtures containing two competitive boronic acids revealed either narcissistic or social self-sorting depending on the stability of the segregated cages relative to feasible three-component assemblies.
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