Journal
ORGANIC LETTERS
Volume 19, Issue 11, Pages 3001-3004Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01235
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Funding
- Polish National Science Centre [2011/02/A/STS/00439]
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The DITIPIRAM (8-propyldithieno[3,2-b:2',3'-e]pyridine-3,5-diamine)-based receptors 11 and 12 were readily synthesized, and their anion-binding properties were studied both in solution and in the solid-state. 1H NMR titrations revealed that receptor 12 equipped with two phenyl-urea groups preferentially binds carboxylates, even in the highly competitive DMSO-d6/CD3OH solvent mixture. X-ray analysis showed that receptor 12 exhibited great complementarity for benzoate, which is cooperatively bound by the means of four highly directional hydrogen bonds from the two urea groups. Comparison with the most effective acyclic receptors based on a structurally related rigid carbazole platform demonstrates that the DITIPIRAM motif provides a better suited geometry in the binding pocket, and consequently stronger anion binding.
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