ArticleJournal of the American Chemical Society2026
Regioselective Synthesis of Ambipolar B-N Lewis Pair Functionalized Pyrenes: Structural Dynamics, Emission Tuning, and Applications in Live Cell Imaging and as Electrochemiluminescent Materials.
Article in Journal of the American Chemical Society, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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10 authors.
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Abstract
Intramolecular B←N Lewis pair functionalization of polycyclic aromatic hydrocarbons (PAHs) is emerging as a powerful strategy for tailoring their optical and electronic properties to specific applications. Herein, we report the design and synthesis of four quadrupolar pyrene fluorophores containing triarylamine donor and pyridyl-borane acceptor substituents by N-directed electrophilic C-H borylation in the K-region. Introduction of rigid six-membered B-N heterocycles greatly decreased the lowest unoccupied molecular orbital (LUMO) energy levels and red-shifted the absorption and emission maxima compared to the nonborylated precursors. These pyrenes exhibit absorptions spanning the entire visible region and intense green to deep red and near-infrared fluorescence, with impressive quantum yields as high as 82%. The simultaneous presence of pyridyl-borane acceptor and arylamine donor units also enables facile reversible multiredox oxidation and reduction processes. The advantageous photophysical and electrochemical characteristics are highly attractive for optoelectronic devices and (bio)imaging applications. The pyrene derivative with the most red-shifted emission,
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