Syntheses, Anion Recognition and Self-assemblies of Cyanostilbene Receptors

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The long term goal of this project is to address one of the grand challenges in the chemical sciences: How to design and perfect the atom- and energy-efficient synthesis of new forms of matter with tailored properties. To this end, Dr. Amar H. Flood at Indiana University seeks knowledge of how to design star-shaped molecules bearing holes in their centers to recognize and hold unique classes of negatively charged anions that were once considered too large to catch. By doing so, this research and these molecules can have impacts in removing toxic anions from contaminated water or manipulating anions important for human health. In addition, his research team investigates how star-shaped structures can be designed to self-assemble and fit together to form larger assemblies, e.g., nanometer-sized, soccer-ball shaped architectures. He aims to unfold the rules of their self-assembly because molecules cannot be picked and placed together like a lego set. Such materials could have impacts in compartmentalized chemical catalysis and for gated drug delivery. Broader impact activities of the project include training of graduate and undergraduate students, using 3D printing to teach principles of self-assembly, and developing strategies to increase the participation and visibility of under-represented minorities and women at conferences organized by Dr. Flood.Under the support of the Macromolecular, Supramolecular and Nanochemistry Program of NSF, Dr. Flood seeks to develop the syntheses of polycyanostilbene macrocycles called "cyanostars" for binding anions (e.g., biorelevant phosphates), and understand fundamentally how non-covalent interactions (such as CH H-bonding) and solvophobic effects influence anion binding. Furthermore, he explores the use of cyanostars in rotaxanes that can switch between states and in novel self-assembled architectures that stem from anion templation and 5-fold symmetry.