Bispidine as a Versatile Scaffold: From Topological Hosts to Transmembrane Transporters

Abstract

AbstractThe development of designer topological structures is a synthetically challenging endeavor. We present herein bispidine as a platform for the design of molecules with various topologies and functions. The bispidine‐based acyclic molecule, which shows intriguing S‐shape topology, is discussed. Single‐crystal X‐ray diffraction studies revealed that this molecule exists in the solid state as two conformational enantiomers. In addition, bispidine‐based designer macrocycles were synthesized and investigated for ionophoric properties. Patch clamp experiments revealed that these macrocycles transport both anions and cations non‐specifically with at least tenfold higher chloride conductance over the cations under the given experimental conditions. Ultramicroscopy and single‐crystal X‐ray crystallographic studies indicated that the self‐assembling macrocycle forms a tubular assembly. Our design highlights the use of unconventional dihydrogen interactions in nanotube fabrication.