Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 13, Pages 4935-4953Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo040276f
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A new series of nitrogen heterocyclic dehydroannulenes 1-3 have been synthesized and their macrocyclic structures assigned using spectroscopic methods. The chiral and planar ground state conformations of 1 and 3, respectively, were determined by semiempirical theoretical calculations. All dehydropyridoannulenes and precursors possessing four aromatic rings functioned as fluorescent chromophores. A detailed spectroscopic investigation into the cation-binding properties of 3 in dilute solution revealed a particularly selective photoluminescence quenching sensory response for Pd-II ions. Cycle 3, as well as 1 and 2, also exhibited reversible proton-triggered luminescence quenching behavior. At higher concentrations, 3 afforded a coordination polymer precipitate with Ag-I ions. Cycles I and 2 and precursors 15, 23, and 29 also undergo thermochemical reactions that may potentially lead to carbon-rich polymers. The physicochemical properties of 1-3 suggest that dehydropyridoarmulenes may serve as a particularly versatile new class of ligands for the creation of novel heteroatom-containing carbon-rich materials with many potential applications in supramolecular materials science and nanotechnology.
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