Synthesis,functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent

Bulky perneopentyloxy-pillar[5]arene (Pillar-1) was synthesized and its conformational mobility was investigated using variable-temperature ¹H NMR spectroscopy. The host–guest interactions between Pillar-1 and n-octyltrimethylammonium hexafluorophosphate (OMA) were investigated, and the formation of a 1 : 1 complex was revealed via¹H NMR. Planar-chiral isomers were synthesized via the reaction of a hydroxy-functionalized pillar[5]arene with chiral derivatization agent (S)-(+)-MTPA-Cl. The (Sp, R)-and (Rp, R)-forms of the pillar[5]arene diastereomers were isolated by HPLC, and their structures were analyzed by ¹⁹F NMR. HPLC measurements indicated that racemization did not take place at 40 °C for 72 h.

Bulky perneopentyloxy-pillar[5]arene was synthesized. Complexation behavior and conformational mobility were investigated using ¹H NMR spectroscopy. Isolation of planar-chiral pillar[5]arenes using a chiral derivatization agent were carried out.