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 (1)H NMR spectroscopy. The host–guest interactions between Pillar-1 and n-octyltrimethylammonium hexafluorophosphate (OMA) were investigated, and the formation...

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Autores principales: Al-Azemi, Talal F., Vinodh, Mickey, Alipour, Fatemeh H., Mohamod, Abdirahman A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9067291/
https://www.ncbi.nlm.nih.gov/pubmed/35514477
http://dx.doi.org/10.1039/c9ra03135a
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author Al-Azemi, Talal F.
Vinodh, Mickey
Alipour, Fatemeh H.
Mohamod, Abdirahman A.
author_facet Al-Azemi, Talal F.
Vinodh, Mickey
Alipour, Fatemeh H.
Mohamod, Abdirahman A.
author_sort Al-Azemi, Talal F.
collection PubMed
description Bulky perneopentyloxy-pillar[5]arene (Pillar-1) was synthesized and its conformational mobility was investigated using variable-temperature (1)H 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(1)H 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 (19)F NMR. HPLC measurements indicated that racemization did not take place at 40 °C for 72 h.
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spelling pubmed-90672912022-05-04 Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent Al-Azemi, Talal F. Vinodh, Mickey Alipour, Fatemeh H. Mohamod, Abdirahman A. RSC Adv Chemistry Bulky perneopentyloxy-pillar[5]arene (Pillar-1) was synthesized and its conformational mobility was investigated using variable-temperature (1)H 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(1)H 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 (19)F NMR. HPLC measurements indicated that racemization did not take place at 40 °C for 72 h. The Royal Society of Chemistry 2019-07-26 /pmc/articles/PMC9067291/ /pubmed/35514477 http://dx.doi.org/10.1039/c9ra03135a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Al-Azemi, Talal F.
Vinodh, Mickey
Alipour, Fatemeh H.
Mohamod, Abdirahman A.
Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent
title Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent
title_full Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent
title_fullStr Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent
title_full_unstemmed Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent
title_short Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent
title_sort synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9067291/
https://www.ncbi.nlm.nih.gov/pubmed/35514477
http://dx.doi.org/10.1039/c9ra03135a
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