Design, synthesis and anion binding studies of a series of novel, acyclic anion binding agents

ORGN 786

Joanthan L. Sessler, sessler@mail.utexas.edu1, Natalie Barkey, nbarkey@cm.utexas.edu1, G. Dan Pantos, pantos@mail.utexas.edu1, and Philip A. Gale, philip.gale@soton.ac.uk2. (1) Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 7812-1167, (2) School of Chemistry, University of Southampton, Southampton, SO17 1BJ, United Kingdom
The design and synthesis of novel receptors with the ability to selectively recognize or bind a specific class of anions is a rapidly developing field of supramolecular chemistry.1,2 A series of novel, acyclic, pyrrole-based anion receptors have recently been synthesized and studied in the Sessler group (Figure 1). The first receptor synthesized (DPPic) was found to have selectivity for nitrite over nitrate, but to also bind acetate, benzoate and cyanide anions. It is stabilized in the conformation shown by the presence of six intramolecular hydrogen bonds. The remaining receptors (DPPic II, DPIPh and RA DPPic) were synthesized to probe the possible role of various conformational and structural effects on binding ability. Each perturbation was found to have drastic effects on the binding properties of the receptor.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

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