The ability to detect biologically relevant small molecules with high levels of selectivity, sensitivity, and broad applicability for a variety of analytes in a variety of complex environments is an important goal in bioanalytical chemistry. Methods to achieve such detection vary widely, and include the use of electrochemical, spectroscopic, and visible read-out signals. The use of supramolecular chemistry to accomplish such detection has a number of notable advantages, including straightforward tunability, high general applicability, and ease of modification of every component. Reported herein is the use of supramolecular chemistry of pillar[5]arenes to accomplish precisely such detection. A variety of pillar[5]arenes have been synthesized and analyzed for their applicability toward small molecule detection schemes. Water-soluble pillar[5]arenes functionalized with cationic pendant arms have been found to bind small molecule toxicants in their hydrophobic cavities with association constants on the orders of 105 and 106 M-1. Using exchange resins, the cationic pillar[5]arenes could be removed from solution along with their encapsulated guests, allowing for potential application to water purification systems. Pillararene-based polymer networks and fluorophore-appended pillararenes have also been developed and found to respond uniquely to small molecule guests, allowing for the development of an array-based detection scheme.

Functionalized pillar arenes for removal of small molecule toxicants and the development of a novel array based detection system

256th National Meeting (2018)

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