Dr. Michael Huggins Research

Anion binding has become an area of intense interest in molecular recognition chemistry with potential applications in the chemical and biological worlds for extraction of pollutants, sensor development, medical applications, and various other areas. We are focusing on preparing pyrrole-based receptors for anions that possess an OH moiety (hydrogen sulfate, dihydrogen phosphate, etc) by including an appropriate hydrogen bond acceptor in the molecular architecture.

MOLECULAR RECOGNITION STUDIES WITH 
DIPYRRINONE DERIVATIVES

Recently, we have shown this approach to be reasonably successful with a simple dipyrrinone-based receptor which was selective for hydrogen sulfate (KA = 1680 M-1). Unfortunately, this simple analog has limited versatility due to its relatively strong self-association (KA= 3850 M-1). Current results with modified dipyrrinones containing C(9) substituents (amides, imines, and sulfonamides) meant to disrupt the self-association will be discussed.

Huggins reaction scheme1

 

DEVELOPMENT OF 
PYRROLE AMIDES AND PYRROLE SULFONAMIDES 
AS POTENTIAL MOLECULAR RECEPTORS

Our efforts in the field are working toward the development of anion receptors that can prepared in short, facile synthesis using various pyrrole analogs. Specifically, we have developed the synthetic routes for the preparation of simple pyrrole 2-amide and 2-sulfonamide derivatives. These systems are being investigated for the molecular recognition properties.

huggins reaction scheme 2