Barbiturates
are common targets for molecular recognition in preorganized
receptors due to complementary hydrogen-bond donor/acceptor interactions.
Although many such receptors exhibit high selectivity and affinity
for barbiturate guests, relatively few of these systems have desirable
photophysical properties for sensing applications. Here, we report
the synthesis, optoelectronic properties, and binding affinities of
a suite of fluorescent arylethynyl Hamilton receptors. We also provide
insights into the design principles required for efficient fluorogenic
design of these systems to function as fluorescent barbiturate sensors.