Anion Transport with Chalcogen Bonds.
- Benz S Department of Organic Chemistry, University of Geneva , CH-1211 Geneva, Switzerland.
- Macchione M Department of Organic Chemistry, University of Geneva , CH-1211 Geneva, Switzerland.
- Verolet Q Department of Organic Chemistry, University of Geneva , CH-1211 Geneva, Switzerland.
- Mareda J Department of Organic Chemistry, University of Geneva , CH-1211 Geneva, Switzerland.
- Sakai N Department of Organic Chemistry, University of Geneva , CH-1211 Geneva, Switzerland.
- Matile S Department of Organic Chemistry, University of Geneva , CH-1211 Geneva, Switzerland.
- 2016-07-20
Published in:
- Journal of the American Chemical Society. - 2016
English
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.
- Language
-
- English
- Open access status
- green
- Identifiers
-
- DOI 10.1021/jacs.6b05779
- PMID 27433964
- Persistent URL
- https://sonar.ch/global/documents/171093
Statistics
Document views: 38
File downloads:
- Full-text: 0