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

ABSTRACT: 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 via ¹H 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.

SUBMITTER: Al-Azemi TF

PROVIDER: S-EPMC9067291 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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

Al-Azemi Talal F TF Vinodh Mickey M Alipour Fatemeh H FH Mohamod Abdirahman A AA

RSC advances 20190726 40

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 via 1H NMR. Planar-chiral isomers were synthesized via the reaction of a hydroxy-functionalized pillar[5]arene with chiral deri ...[more]

PMID: 35514477

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