| Abstract
| - A new series of nitrogen heterocyclic dehydroannulenes 1−3 have been synthesized and theirmacrocyclic structures assigned using spectroscopic methods. The chiral and planar ground stateconformations of 1 and 3, respectively, were determined by semiempirical theoretical calculations.All dehydropyridoannulenes and precursors possessing four aromatic rings functioned as fluorescentchromophores. A detailed spectroscopic investigation into the cation-binding properties of 3 in dilutesolution revealed a particularly selective photoluminescence quenching sensory response for PdIIions. Cycle 3, as well as 1 and 2, also exhibited reversible proton-triggered luminescence quenchingbehavior. At higher concentrations, 3 afforded a coordination polymer precipitate with AgI ions.Cycles 1 and 2 and precursors 15, 23, and 29 also undergo thermochemical reactions that maypotentially lead to carbon-rich polymers. The physicochemical properties of 1−3 suggest thatdehydropyridoannulenes may serve as a particularly versatile new class of ligands for the creationof novel heteroatom-containing carbon-rich materials with many potential applications in supramolecular materials science and nanotechnology.
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