Spotlights on Recent JACS Publications

摘要

Aryl boronic acids are among the most versatile molecular building blocks in supramolecular chemistry and materials science. Despite their ease of preparation and dynamic covalent reactivity, and the structural diversity of aromatic boronic acids, researchers have marginally explored their ability to participate in hydrogen bonding with other molecules for applications in molecular recognition. Now, Davide Bonifazi and his team describe the first combined study of solution-phase and solid-state aromatic boronic acids interacting via hydrogen bonds with complementary acceptor molecules (DOI: 10.1021/jacs.6b11362). Here, boronic acids can self-adapt while retaining their recognition properties, taking on different shapes depending on the bulkiness of substituents. A supramolecular hydrogen-bonded polymeric ribbon is constructed through the donor—acceptor interaction between a diboronic acid and a tetraazanaphthacene. The findings may lead to developments in design of programmed boronic acids as a potent building block through hydrogen bond recognition to construct supramolecular complexes with unique structural and physical properties for applications in organocatalysis and in engineering of functional organic materials and printed electronics.