Supramolecular studies on aromatic propargylic alcohols modified with aliphatic chains

CHED 318

Ashleigh R. Borges1, Kevin L. Caran, carankl@jmu.edu1, Marilise A. Hyacinth, mh5ua@virginia.edu2, Michal Sabat, ms5c@virginia.edu2, and Lin Pu, lp6n@virginia.edu2. (1) Department of Chemistry, James Madison University, MSC 4501, Harrisonburg, VA 22807, (2) Department of Chemistry, University of Virginia, McCormick Rd., Charlottesville, VA 22904
A number of chiral aromatic propargylic alcohols have recently been found to display interesting supramolecular interactions in the solid state based on three intermolecular interactions: OH•••O hydrogen bonds, aromatic-fluoroaromatic pi stacking, and weak CH•••F hydrogen bonds. Several derivatives display hexameric aggregates that stack into columns containing pseudo-infinite channels a few angstroms wide. Our current efforts include modifying these structures with aliphatic hydrocarbons of different chain lengths and investigating the supramolecular behavior of these structures in various environments. Such modifications may promote the formation of fibrous aggregates with a high aspect ratio by suppressing aggregation lateral to the direction of fiber growth. Synthesis and colloidal studies of these molecules will be presented.
 

Undergraduate Research Poster Session: Organic Chemistry
2:30 PM-4:30 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Poster

Division of Chemical Education

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006