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Importance of Precursor Adaptability in the Assembly of Molecular Organic Cages.

Manuel RondelliAntonio Hernández DaranasTomás Martín
Published in: The Journal of organic chemistry (2023)
For molecular architectures based on dynamic covalent chemistry (DCvC), strict preorganization is a paradigmatic concept and the generally accepted strategy for their rational design. This results in the creation of highly rigid building blocks which are expected to fulfill the ideal geometry of the assembly, coming at a price that small geometric mismatches result in unpredicted and/or unproductive reaction outcomes. In this study, we show that feet of a tripodal platform have a great influence on the assembly of tetrahedral organic cages based on boronate ester formation. The aryl benzyl ether-functionalized building blocks perform significantly better than their alkyl-functionalized equivalents. Experimentally and using density functional theory geometry optimization of the cage structures, we prove that unexpectedly, this is not due to solubility but because of the enhanced capability of the aryl benzyl ether-functionalized building blocks to fit the ideal geometry of the assembly. This introduces the concept of building block adaptability to overcome geometrical mismatches in DCvC systems.
Keyphrases
  • density functional theory
  • quantum dots
  • ionic liquid
  • molecular dynamics
  • molecularly imprinted
  • high resolution
  • high throughput
  • single molecule
  • metabolic syndrome
  • insulin resistance
  • single cell
  • skeletal muscle