Dimerization and anion binding of a fluorescent phospholipid analogue.

J Org Chem

Department of Chemistry, Science and Technology Building, East Carolina University, Greenville, North Carolina 27858-4353, USA.

Published: August 2012

A diarylacetylene fluorophore featuring spatially separated urea and phosphocholine (PC) groups forms a macrocyclic "head-to-tail" dimer stabilized by NH(urea)···OP(PC) hydrogen bonds. At concentrations above ~2 × 10(-5) M in CH(2)Cl(2), the emission intensity of the dimer is quenched by HCO(3)(-) and H(2)PO(4)(-) but not by Cl(-) and NO(3)(-). Under more dilute conditions, all four anions are bound unselectively with association constants on the order of 10(5) M(-1).

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http://dx.doi.org/10.1021/jo3009758DOI Listing

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