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Uncharged organic molecule can bind negatively charged ions
Date:2/26/2008

d Li's solution was to create a donut-shaped organic molecule whose center would serve as the binding spot. A halide ion might fit snugly inside the hole, but the arrangement of atoms surrounding the hole would exclude any solutions.

Flood also wanted the synthesis of such a molecule to be cheap, easy and flexible, so he looked to the "click chemistry" devised by Scripps Research Institute chemist K. Barry Sharpless. Click chemistry is an efficient method of joining molecules together to form larger molecules. Flood's particular application of click chemistry results in an eight-member macrocycle with a 3.7 angstrom hole in the middle. The more-or-less symmetrical molecule that Flood and Li built contains four triazole rings sporting three nitrogen atoms each. It is presumed the nitrogens withdraw electron density from the carbon and hydrogen atoms closest to the molecule's hole, thereby creating an alluring binding spot for fluorine or chlorine ions. This binding is made all the more orderly because the macrocycle is preorganized to host its anionic guest.

"This thing is so easy to make," Flood said. "The triazole moiety has got more character to it than meets the eye. It's not just a byproduct of the click chemistry. We see lots of potential in it."

The other four members of Flood and Li's eight-member ring are entirely substitutable. Modifying these may give the chelator different binding affinities for a given anion.


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Contact: David Bricker
brickerd@indiana.edu
812-856-9035
Indiana University
Source:Eurekalert  

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