Anion Transport with Chalcogen Bonds.

In this report, we introduce synthetic anion transporters that operate with chalcogen bonds. Electron-deficient dithieno[3,2-b;2',3'-d]thiophenes (DTTs) are identified as ideal to bind anions in the focal point of the σ holes on the cofacial endocyclic sulfur atoms. Anion binding in solution and anion transport across lipid bilayers are found to increase with the depth of the σ holes of the DTT anionophores. These results introduce DTTs and related architectures as a privileged motif to engineer chalcogen bonds into functional systems, complementary in scope to classics such as 2,2'-bipyrroles or 2,2'-bipyridines that operate with hydrogen bonds and lone pairs, respectively.

Citation

Sebastian Benz, Mariano Macchione, Quentin Verolet, Jiri Mareda, Naomi Sakai, Stefan Matile. Anion Transport with Chalcogen Bonds. Journal of the American Chemical Society. 2016 Jul 27;138(29):9093-6

PMID: 27433964

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