Synthesis, purification, and characterization of a highly fluorinated dendrimer

CHED 500

Jeremy B. Stegall, jbstegall@roanoke.edu1, W. Gary Hollis Jr., hollis@roanoke.edu1, and Paul A. Deck, pdeck@vt.edu2. (1) Department of Chemistry, Roanoke College, 221 College Lane, Salem, VA 24153, (2) Department of Chemistry, Virginia Tech, 107 Davidson Hall, Blacksburg, VA 24061-0212
A symmetric, high molecular weight, and highly fluorinated dendrimer was synthesized by means of a Diels-Alder reaction between perfluorotetraphenylcyclopentadienone and 1,3,5-triethynylbenzene. A high temperature and extended reaction method for preparation of the dendrimer was developed. The molecule was ultimately purified by column chromatography using solutions of ethyl acetate in hexane and characterized by NMR spectroscopy. 1,3,5-Triethynylbenzene was synthesized from 1,3,5-tribromobenzene via Sonogashira coupling methodology. This initial synthesis will allow for further study of the molecular properties of the dendrimer, effects of high fluorination, and optimization of reaction conditions to allow for a more optimum yield of the novel compound.

 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008