Carbonyl groups as molecular valves to regulate chloride binding to squaramides.
Environment-sensitive binding of anions to synthetic receptors is important for the functional mimicry of ion channels. We describe new squaramide-based chloride ion receptors whose anion binding cavity can be opened and closed by using carbonyl groups as valves. In nonpolar solvents, the carbonyls preclude chloride binding via intramolecular hydrogen bonding with the squaramide NHs. In polar solvents, disruption of the intramolecular hydrogen bonds reorients the carbonyl groups and opens the anion-binding cavity.
Ramalingam
Vijayakumar
V
Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York 11367-1597, USA.
Domaradzki
Maciej E
ME
Jang
Seogjoo
S
Muthyala
Rajeev S
RS
D000577:Amides / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry; D018118:Chloride Channels / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D003503:Cyclobutanes / Q000737:chemistry*; D007473:Ion Channels / Q000737:chemistry
D000577:Amides; D018118:Chloride Channels; D002712:Chlorides; D003503:Cyclobutanes; D007473:Ion Channels; C030042:squaric acid