This proposal addresses the correlation of physical, spectroscopic, chemical and biological effects of boronic acid substitution on flavonoid subclasses. Specific objectives include: (1) synthesis of a new subclass of synthetic flavonoids -boronic acid substituted chalcones (BASCs), (2) development of deeply colored BASCs as (a) novel molecular sensors for cyanide and amines, (b) solvatochromic indicators, (c) DNA photonucleases, and (d) NIR absorbing dyes, (3) investigation of the antimicrobial activity of hydroxylated BASCs, and (4) use of BASCs as model systems for the development of other boronic acid substituted flavonoids (aurones, flavones, anthocyanins). The 'ortho Lewis acid effect' highlighted in these compounds will be assessed calculationally and applied in the rational design and development of tunable electron acceptor subunits for internal charge transfer (ICT) materials.<br/><br/>With the support of a Research at Undergraduate Institutions award from the Organic and Macromolecular Chemistry Program, Professor Desmond H. Murray, of the Department of Chemistry at Andrews University, is studying the synthesis and properties of a unique class of molecules that incorporate two unusual substructures. The juxtaposition of these two "functional groups" leads to a diverse range of unusual and important molecular properties, leading to potential applications in the areas of molecular sensors for toxic environmental and industrial agents, molecular sensors for a-hydroxy acids and carbohydrates for agricultural, food and medical applications, and novel antimicrobial agents. Professor Murray's research program actively involves a diverse group of undergraduates and high school students, improves the levels of inclusion of research-active students from underrepresented groups, and provides early opportunities for students to experience the excitement of scientific discovery.