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Host selectivity behaviour of trans-N,N′-bis(9-phenyl-9-xanthenyl)cyclohexane-1,2-diamine and trans-N,N′-bis(9-phenyl-9-thioxanthenyl)cyclohexane-1,2-diamine when presented with six-membered heterocyclic guest mixtures

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Abstract

Two compounds, trans-N,N′-bis(9-phenyl-9-xanthenyl)cyclohexane-1,2-diamine (1,2-DAX) and trans-N,N′-bis(9-phenyl-9-thioxanthenyl)cyclohexane-1,2-diamine (1,2-DAT), were assessed for their host ability in the presence of four heterocyclic guest species, namely pyridine (PYR), piperidine (PIP), morpholine (MOR) and dioxane (DIO). Each of these guests formed single solvent complexes with both host compounds. When 1,2-DAX and 1,2-DAT were recrystallized from various guest mixtures, it was shown that their selectivity orders were identical, DIO (46.6%) > MOR (23.0%) > PYR (18.9%) > PIP (11.5%) and DIO (85.9%) > MOR (23.7%) > PYR (8.9%) > PIP (8.5%), respectively, but that the thio host derivative possessed a significantly enhanced preference for DIO compared with its oxygen analogue. Additional experiments in order to investigate the various parameters at play in these complexation experiments involved single crystal diffraction experiments and thermal analyses.

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Acknowledgements

Financial support is acknowledged from the Nelson Mandela University and the National Research Foundation (NRF).

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Authors and Affiliations

  1. Department of Chemistry, Nelson Mandela University, PO Box 77000, Port Elizabeth, 6031, South Africa

    Benita Barton, Daniel V. Jooste & Eric C. Hosten

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  1. Benita Barton
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  2. Daniel V. Jooste
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  3. Eric C. Hosten
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Correspondence to Benita Barton.

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Supplementary Information

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10847_2021_1069_MOESM1_ESM.docx

Crystallographic data for the novel complexes presented in this work were deposited at the Cambridge Crystallographic Data Centre {CCDC-2024256 [2(1,2-DAX)·5(PIP)], 2,024,255 [1,2-DAX·2(MOR)], 2,024,257 [1,2-DAX·2(DIO)], 2,024,259 [1,2-DAT·2(PIP)], 2,024,258 [1,2-DAT·2(MOR)] and 2,024,260 [1,2-DAT·2(DIO)]}. [Note that 1,2-DAX·2(PYR) and 1,2-DAT·PYR were reported before and in a different context (CCDC-2006097 and 2,006,101, respectively) [14]]. These data may be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Figures S1a–h are the overlaid DSC, TG and DTG traces obtained from the thermal experiments. Supplementary file1 (DOCX 468 kb)

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Barton, B., Jooste, D.V. & Hosten, E.C. Host selectivity behaviour of trans-N,N′-bis(9-phenyl-9-xanthenyl)cyclohexane-1,2-diamine and trans-N,N′-bis(9-phenyl-9-thioxanthenyl)cyclohexane-1,2-diamine when presented with six-membered heterocyclic guest mixtures. J Incl Phenom Macrocycl Chem 100, 177–188 (2021). https://doi.org/10.1007/s10847-021-01069-3

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