Synthesis of Chiral Helic[1]triptycene[3]arenes and Their Enantioselective Recognition towards Chiral Guests Containing Aminoindan Groups

Abstract

Starting from the enantiopure precursors, a pair of chiral macrocyclic arenes named helic[1]triptycene[3]arenes were conveniently synthesized. The circular dichroism (CD) spectra of the enantiomeric macrocyclic arenes exhibited mirror images, and the X-ray single crystal structures confirmed their absolute conformations as well. Moreover, the macrocyclic arenes showed strong complexation with secondary ammonium and primary ammonium salts containing aminoindan groups. In particular, the chiral macrocyclic arenes exhibited enantioselective recognition ability towards the chiral secondary ammonium salts containing aminoindan groups with an enantioselective ratio up to 3.89.

Keywords

• macrocyclic arene
• enantioselective recognition
• helic[1]triptycene[3]arene
• ammonium salts