Department of Organic Chemistry, University of Geneva , CH-1211 Geneva, Switzerland.
J Am Chem Soc. 2016 Jul 27;138(29):9093-6. doi: 10.1021/jacs.6b05779. Epub 2016 Jul 19.
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.
在本报告中，我们介绍了使用硫属键运作的合成阴离子转运体。电子缺电子二噻吩并[3,2-b;2',3'-d]噻吩（DTTs）被确定为理想的在共面内环硫原子上的σ孔的焦点处结合阴离子。发现阴离子在溶液中的结合和阴离子穿过脂质双层的转运随着 DTT 阴离子载体的σ孔的深度增加而增加。这些结果将 DTT 及其相关结构引入到功能系统中，将硫属键工程化，与经典的 2,2'-联吡啶或 2,2'-联吡啶互补，它们分别通过氢键和孤对运作。
