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Selective Synthesis and Functionalization of an Acyclic Methylene‐Bridged‐Arene Trimer in a Cage

Hiroki Takezawa, Kenta Iizuka, Makoto Fujita

2023Angewandte Chemie International Edition19 citationsDOIOpen Access PDF

Abstract

Arene-formaldehyde condensation is a versatile reaction for producing various oligomeric/polymeric materials. However, the precise control of oligomerization degree is still challenging because the starting materials and intermediates have similar reactivities. Here, we demonstrate the selective synthesis of a methylene-bridged arene trimer using the confined cavity of a coordination cage. The limited space of the cavity prevents unregulated polymerization. The confinement effect for the kinetic protection is also demonstrated by the subsequent site-selective iodination of the trimer product within the cage.

Topics & Concepts

TrimerChemistryMethyleneCagePolymerizationFormaldehydeSurface modificationCondensationPolymer chemistryStereochemistryCombinatorial chemistryOrganic chemistryPolymerDimerPhysical chemistryMathematicsPhysicsThermodynamicsCombinatoricsSupramolecular Chemistry and ComplexesCrystallography and molecular interactionsBoron Compounds in Chemistry
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