The strong affinity of 1 and 2 for halides, together with their high lipophilicity, prompted us to study their ability to transport chloride anions across lipid bilayers. In biological systems, anion transport through lipophilic membranes plays important roles in many essential biochemical processes, such as cellular respiration, signal transduction, pH regulation, and removal of metabolic products. In living organisms, this task is performed by numerous specialized anionophores, and their failure often leads to severe diseases, such as cystic fibrosis, anemia, congenital myotonia, deafness, diabetes, and cancer. Accordingly, considerable research efforts have been devoted to the development of artificial anionophores, motivated by the prospect of curing these diseases through the displacement of dysfunctional proteins. This is challenging though, because the nonselective transport of ions might perturb complex ion homeostasis to the extent that the transporters become toxic. In particular, most NH-bonding transporters discharge proton gradients that are critical for maintaining life functions. It is therefore particularly important to develop highly selective, non-protonophoric anion transporters. One of the most promising approaches to achieving this goal is based on the use of receptors that are highly resistant to deprotonation, such as the CH-hydrogen bonding receptors described herein.