Issue 25, 2021

Comparing the host behaviour of roof-shaped compounds trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid and its dimethyl ester in the presence of mixtures of xylene and ethylbenzene guests

Abstract

Here we compare the host behaviour of two roof-shaped compounds, trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid H1 and its dimethyl ester, trans-dimethyl 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate H4, when presented with mixed xylene (o-Xy, m-Xy and p-Xy) and ethylbenzene (EB) guest solutions. Both host compounds formed complexes with all of these solvents, except H4/EB, where no inclusion occurred. When H1 was recrystallized from the various equimolar combinations of these guests, enhanced selectivities were observed for p-Xy. In fact, equimolar binary mixtures of o-Xy/p-Xy and m-Xy/p-Xy afforded complexes that showed near-complete host selectivity for p-Xy (96.6 and 93.6%, respectively). The selectivity displayed by H4 in analogous experimental conditions, however, was only ordinary at best. The complexes of H1 and H4 with p-Xy were explored in-depth by means of single crystal diffraction analyses. Owing to the scarcity in the number and type of host⋯guest interactions, both complexes may be defined as approaching that of true clathrates. Finally, data from thermoanalytical experiments concurred with the selectivity behaviour of both host compounds.

Graphical abstract: Comparing the host behaviour of roof-shaped compounds trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid and its dimethyl ester in the presence of mixtures of xylene and ethylbenzene guests

Supplementary files

Article information

Article type
Paper
Submitted
03 မေ 2021
Accepted
03 ဇွန် 2021
First published
03 ဇွန် 2021

CrystEngComm, 2021,23, 4560-4572

Comparing the host behaviour of roof-shaped compounds trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid and its dimethyl ester in the presence of mixtures of xylene and ethylbenzene guests

B. Barton, U. Senekal and E. C. Hosten, CrystEngComm, 2021, 23, 4560 DOI: 10.1039/D1CE00594D

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