Issue 12, 2023

Complementary host behaviour of three anthracenyl-derived roof-shaped compounds in mixed pyridines

Abstract

Dimethyl trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate (H1), trans-α,α,α′,α′-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (H2) and trans-α,α,α′,α′-tetra(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (H3) were investigated for their host ability for pyridine and 2-, 3- and 4-methylpyridine (Py, 2MePy, 3MePy and 4MePy) by means of recrystallization experiments from these organic solvents. Each one was enclathrated with the exception of H2 in 4MePy where a gel resulted in the experiment. Subsequently, guest/guest competition experiments were conducted, and it was noted that each of the three host compounds possessed complementary selectivities: H1 preferred Py, H2·3MePy and H3·2MePy in such conditions. H1 was also observed to extract large amounts of Py from a 70.1% Py/29.9% 4MePy mixture and the selectivity coefficient, K, was 11.9 (in favour of Py), ensuring that such mixtures may be separated by means of host–guest chemistry strategies. Single crystal X-ray diffraction experiments and thermal analyses were employed, where possible, in order to explain these selectivity observations by investigating both the host⋯guest interactions present in the complexes and their relative thermal stabilities, respectively.

Graphical abstract: Complementary host behaviour of three anthracenyl-derived roof-shaped compounds in mixed pyridines

Supplementary files

Article information

Article type
Paper
Submitted
26 जनवरी 2023
Accepted
24 फरवरी 2023
First published
28 फरवरी 2023

CrystEngComm, 2023,25, 1740-1754

Complementary host behaviour of three anthracenyl-derived roof-shaped compounds in mixed pyridines

B. Barton, M. R. Caira, U. Senekal and E. C. Hosten, CrystEngComm, 2023, 25, 1740 DOI: 10.1039/D3CE00080J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements