各校計畫成果

活動簡介

Growing technological and energy demands require clean energy technologies, energy-efficient electronics, and effective catalysts. These innovations should prioritize low costs and should avoid rare and toxic elements. Towards these goals, organic π-conjugated structures are central to emerging technologies such as organic transistors, organic light-emitting diodes, organic solar cells, and organocatalysts. The Farrell laboratory's research program explores the frontiers of organic π-systems, developing new synthetic methods to achieve unprecedented π-conjugated structures. In contrast to traditional 2D hexagonal carbon frameworks, these new π-frameworks feature precise heteroatom substitutions and/or variations in ring size. The Farrell laboratory studies and optimizes optical and electronic properties of these new compounds, aiming to develop high-performance materials for applications in catalysis and organic electronic devices. In recently published results, the Farrell laboratory has disclosed a new metal-free alkyne annulation reaction that enables π-extension of boron-doped polycyclic aromatic hydrocarbons, revealing an attractive synthesis of desirable low LUMO energy π-systems.

The Farrell laboratory has recently published the discovery of a C−H functionalization annulation reaction of boron-doped polycyclic aromatic hydrocarbons (PAHs) with alkynes [Chem. Sci. 2024, DOI: 10.1039/d4sc03781b]. This metal-free π-extension offers a novel annulation strategy for B-doped PAHs, exemplified by the synthesis of a series of functionalized, structurally constrained 6a,15a-diborabenzo[tuv]naphtho[2,1-b]picenes. Regioselectivity and DFT calculations suggest an annulation mechanism involving intramolecular electrophilic aromatic substitution of a zwitterionic intermediate. The annulated compounds exhibit ambient stability, deep LUMO energy levels, strong absorptions in the visible range, and sterically accessible π-systems which vary in their solid-state structures depending on choice of substituents. In light of the growing demand for electron-deficient π-scaffolds for functional materials, the Farrell laboratory enthusiastically continues their studies of these compounds and this new methodology.