Chemists are swapping carbon-carbon bonds for boron-nitrogen bonds inside ring-shaped molecules, creating new chemical scaffolds that do not exist in nature. This matters because the carbon-based molecules that underpin modern medicines, plastics, and electronics have reached their performance limits. The boron-nitrogen replacements—known as isosteres—preserve the ring structure but alter the molecule’s electronic and optical properties. The team will focus on diazaborines, boron-nitrogen analogues of pyridine, a common building block in drugs. They will synthesise these unexplored scaffolds, test their stability in air and water, and run preliminary biological assays. This is fundamental science. There is no immediate practical application. The goal is to expand the chemical space available to medicinal chemists, giving them new molecular frameworks that might eventually yield drugs with better potency, specificity, or lower toxicity. Past work on boron-containing compounds—such as the Suzuki-Miyaura coupling—transformed organic synthesis. If these new scaffolds prove stable and biologically active, they could open routes to therapeutics that carbon-only chemistry cannot reach.
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The chemistry of life is built upon molecules containing covalent carbon-carbon bonds. Such compounds are studied by organic chemists, who have developed advanced methodologies for forming and manipulating carbon-carbon bonds, enabling the creation of a vast array of natural and synthetic carbon-based materials. These compounds can be found in every aspect of our lives – from modern day medicines and colourful toy bricks to OLED dyes in our mobile phone screens, to name just a few. However, the properties achievable with purely carbon-based compounds are limited. To explore novel functional molecules and materials with enhanced features, this research proposal will investigate the replacement of organic carbon-carbon bonds with inorganic boron-nitrogen bonds, a concept known as elemental isosterism. This approach allows for the synthesis of molecules with unique characteristics and reactivities that cannot be achieved by their carbon-based counterparts. In this regard, elemental isosterism offers a powerful strategy to increase structural diversity and expand the accessible chemical space. Boron, positioned next to carbon and nitrogen in the periodic table, two important elements that form the backbone of life, has significant potential in medicinal chemistry. Organoboron derivatives, known for their stability towards air and diverse reactivity, have become crucial reagents in organic synthesis, most notably in the Suzuki-Miyaura coupling. However, their applications outside synthetic uses remain elusive. The proposed research aims to study the synthesis and reactivity of currently unexplored or underexplored boron-containing molecular scaffolds. For arenes and heteroarenes, replacing a carbon-carbon bond with a boron-nitrogen bond is expected to preserve some of the aromatic character. However, due to the polarisation of the B–N bond, the resulting isosteres will exhibit distinct electronic, optical, and chemical properties compared to their carbon-based analogues. In particular, the chemistry of diazaborines, BN analogues of pyridine, will be explored in detail. These novel molecular scaffolds will be thoroughly characterised, and their stability towards air and moisture will be evaluated. Additionally, preliminary studies on their biological activity will be conducted. Modern medicinal chemistry continuously faces the challenge of discovering new lead structures that offer potency, specificity, and low toxicity for treating numerous diseases. The search for new therapeutically useful scaffolds is therefore of great interest. In this context, boron-nitrogen isosterism has the potential to provide novel molecular frameworks with unprecedented biological activities. The concept of BN/CC isosterism will expand the accessible chemical space of organic compounds, offering new possibilities for innovations in medicinal chemistry.
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