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Quantification of Nitrate−π Interactions and Selective Transport of Nitrate Using Calix[4]pyrroles with Two Aromatic Walls

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journal contribution
posted on 2013-06-05, 00:00 authored by Louis Adriaenssens, Carolina Estarellas, Andreas Vargas Jentzsch, Marta Martinez Belmonte, Stefan Matile, Pablo Ballester
Herein we disclose the results of our investigations regarding the interactions between the biologically relevant nitrate oxoanion and several “two-wall” aryl-extended calix[4]­pyrroles. There exists a clear relationship between the electronic nature of the aromatic walls of the calix[4]­pyrroles and the stability of the nitrate⊂calix[4]­pyrrole complex. This suggests that NO3–π interactions have an important electrostatic component. We provide energetic estimates for the interaction of nitrate with several phenyl derivatives. Additionally, we report solid-state evidence for a preferred binding geometry of the nitrate anion included in the calix[4]­pyrroles. Finally, the “two-wall” aryl-extended calix[4]­pyrroles show excellent activity in ion transport through lipid-based lamellar membranes. Notably the best anion transporters are highly selective for transport of nitrate over other anions.

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