Issue 37, 2021

Tuning the porosity of triangular supramolecular adsorbents for superior haloalkane isomer separations

Abstract

Distillation-free separations of haloalkane isomers represents a persistent challenge for the chemical industry. Several classic molecular sorbents show high selectivity in the context of such separations; however, most suffer from limited tunability or poor stability. Herein, we report the results of a comparative study involving three trianglamine and trianglimine macrocycles as supramolecular adsorbents for the selective separation of halobutane isomers. Methylene-bridged trianglamine, TA, was found to capture preferentially 1-chlorobutane (1-CBU) from a mixture of 1-CBU and 2-chlorobutane (2-CBU) with a purity of 98.1%. It also separates 1-bromobutane (1-BBU) from a mixture of 1-BBU and 2-bromobutane (2-BBU) with a purity of 96.4%. The observed selectivity is ascribed to the thermodynamic stability of the TA-based host–guest complexes. Based on single crystal X-ray diffraction analyses, a [3]pseudorotaxane structure (2TA1-CBU) is formed between TA and 1-CBU that is characterized by an increased level of noncovalent interactions compared to the corresponding [2]pseudorotaxane structure seen for TA2-CBU. We believe that molecular sorbents that rely on specific molecular recognition events, such as the triangular pores detailed here, will prove useful as next generation sorbents in energy-efficient separations.

Graphical abstract: Tuning the porosity of triangular supramolecular adsorbents for superior haloalkane isomer separations

Supplementary files

Article information

Article type
Edge Article
Submitted
27 iyn 2021
Accepted
14 avq 2021
First published
16 avq 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 12286-12291

Tuning the porosity of triangular supramolecular adsorbents for superior haloalkane isomer separations

B. Hua, Y. Ding, L. O. Alimi, B. Moosa, G. Zhang, W. S. Baslyman, J. Sessler and N. M. Khashab, Chem. Sci., 2021, 12, 12286 DOI: 10.1039/D1SC03509F

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