Fluorescent Arylethynyl Hamilton Receptors for Barbiturate Sensing

Abstract

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.

A novel Hamilton receptor monomer for the stoichiometric molecular imprinting of barbiturates

“…MIPs selective for barbiturates may find use in a number of different applications: (1) as part of a sensor system for monitoring levels in patient plasma or urine [24]; (2) in solid phase extraction for sample clean-up and enrichment of patient samples prior to analysis, avoiding complications due to sample complexity arising from concomitant use of a range of drug substances [25]; (3) as a putative therapeutic for the capture and removal of barbiturates from a patient's bloodstream following poisoning [26].…”