We have developed a class of modular, inherently fluorescent receptors based on akynyl-functionalized aryl scaffolds as hosts for small molecules and ions. A class of these receptors form 1:1 complexes with halides and exhibits tunable “off-on” or “on-off” fluorescence in the presence of anions, depending on the placement of electron-donating and -withdrawing groups on the periphery of the host. Recent progress on exploring CH anion hydrogen bonding and halogen bonding with heavy p-block elements as “halogen bond donors” within this receptor class will be described. In addition, we serendipitously discovered that precursors to these receptors react in high-yielding, efficient reactions to generate a class of P,N-containing heterocycles known as azaphosphorines. This class of heterocycle features an excellent P=O hydrogen bond acceptor and an acidic NH hydrogen bond donor, suggesting they might be suitable hosts for protic oxoanions. The simplest monomeric heterocycle we have prepared, a phosphaquinoline (which is the P,N-analog of carbostyril or 2-quinolone), forms a strong homodimer in solution, confirming the promise of this receptor class to serve as a hydrogen bond donor and acceptor. This receptor class also features tunable fluorescent properties. This talk will present our current understanding of substituent effects on the optoelectronic properties, dimerization constants, and selectivity/strength of anion binding in this receptor class.

Supramolecular assemblies and anion recognition: Going p-block

256th National Meeting (2018)

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