Boar-q-pine - Avatar: The Last Airbender

Borepins are a class of boron-containing heterocycles used in main group chemistry. They consist of a seven-membered unsaturated ring with a tricoordinate boron in it. Simple borepins are analogues of cycloheptatriene, which is a seven-membered ring containing three carbon-carbon double bonds, each of which contributes 2π electrons for a total of 6π electrons. Unlike other seven-membered systems such as silepins and phosphepins, boron has a vacant p-orbital that can interact with the π and π* orbitals of the cycloheptatriene. This leads to an isoelectronic state akin to that of the tropylium cation, aromatizing the borepin while also allowing it to act as a Lewis acid. The aromaticity of borepin is relatively weak compared to traditional aromatics such as benzene or even cycloheptatriene, which has led to the synthesis of many fused, π-conjugated borepin systems over the years. Simple and complex borepins have been extensively studied more recently due to their high fluorescence and potential applications in technologies like organic light-emitting diodes (OLEDs) and photovoltaic cells.