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Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation
The separation of α-olefins and their corresponding isomers continues to be a big challenge for the chemical industry due to their overlapping physical properties and low relative volatility. Herein, pillar[3]trianglamine (P-TA) macrocycles were synthesized for the molecular-sieving-like separation...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8926253/ https://www.ncbi.nlm.nih.gov/pubmed/35414884 http://dx.doi.org/10.1039/d2sc00207h |
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author | Ding, Yanjun Alimi, Lukman O. Du, Jing Hua, Bin Dey, Avishek Yu, Pei Khashab, Niveen M. |
author_facet | Ding, Yanjun Alimi, Lukman O. Du, Jing Hua, Bin Dey, Avishek Yu, Pei Khashab, Niveen M. |
author_sort | Ding, Yanjun |
collection | PubMed |
description | The separation of α-olefins and their corresponding isomers continues to be a big challenge for the chemical industry due to their overlapping physical properties and low relative volatility. Herein, pillar[3]trianglamine (P-TA) macrocycles were synthesized for the molecular-sieving-like separation of 1-hexene (1-He) selectively over its positional isomer trans-3-hexene (trans-3-He) in the vapor and liquid state. This allyl-functionalized macrocycle features a deeper cavity compared to the previously reported trianglamine host molecules. Solid–vapor sorption experiments verified the successful separation of 1-He from an equimolar mixture of 1-He and trans-3-He. Single-crystal structures and powder X-ray diffraction patterns suggest that this selective adsorption arises from the formation of a thermodynamically stable host–guest complex between 1-He and P-TA. A reversible transformation between the nonporous guest-free structure and the guest-containing structure shows that 1-He separation can be carried out over multiple cycles without any loss of performance. Significantly, P-TA can separate 1-He directly from a liquid isomeric mixture and thus P-TA modified silica sieves (SBA-15) showed the ability to selectively separate 1-He when utilized as a stationary phase in column chromatography. This capitalizes on the prospects of employing macrocyclic hosts as molecular recognition units in real-life separations for sustainable and energy-efficient industrial practices. |
format | Online Article Text |
id | pubmed-8926253 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-89262532022-04-11 Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation Ding, Yanjun Alimi, Lukman O. Du, Jing Hua, Bin Dey, Avishek Yu, Pei Khashab, Niveen M. Chem Sci Chemistry The separation of α-olefins and their corresponding isomers continues to be a big challenge for the chemical industry due to their overlapping physical properties and low relative volatility. Herein, pillar[3]trianglamine (P-TA) macrocycles were synthesized for the molecular-sieving-like separation of 1-hexene (1-He) selectively over its positional isomer trans-3-hexene (trans-3-He) in the vapor and liquid state. This allyl-functionalized macrocycle features a deeper cavity compared to the previously reported trianglamine host molecules. Solid–vapor sorption experiments verified the successful separation of 1-He from an equimolar mixture of 1-He and trans-3-He. Single-crystal structures and powder X-ray diffraction patterns suggest that this selective adsorption arises from the formation of a thermodynamically stable host–guest complex between 1-He and P-TA. A reversible transformation between the nonporous guest-free structure and the guest-containing structure shows that 1-He separation can be carried out over multiple cycles without any loss of performance. Significantly, P-TA can separate 1-He directly from a liquid isomeric mixture and thus P-TA modified silica sieves (SBA-15) showed the ability to selectively separate 1-He when utilized as a stationary phase in column chromatography. This capitalizes on the prospects of employing macrocyclic hosts as molecular recognition units in real-life separations for sustainable and energy-efficient industrial practices. The Royal Society of Chemistry 2022-03-02 /pmc/articles/PMC8926253/ /pubmed/35414884 http://dx.doi.org/10.1039/d2sc00207h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Ding, Yanjun Alimi, Lukman O. Du, Jing Hua, Bin Dey, Avishek Yu, Pei Khashab, Niveen M. Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation |
title | Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation |
title_full | Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation |
title_fullStr | Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation |
title_full_unstemmed | Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation |
title_short | Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation |
title_sort | pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8926253/ https://www.ncbi.nlm.nih.gov/pubmed/35414884 http://dx.doi.org/10.1039/d2sc00207h |
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