Advertisement

Complexes of host compound (−)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) with guests anisole and the methyl-substituted anisoles: host selectivity, thermal and single crystal diffraction considerations

  • Benita BartonEmail author
  • Pieter L. Pohl
  • Eric C. Hosten
Original Article
  • 40 Downloads

Abstract

(−)-(2R,3R)-2,3-Dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) was determined to be a highly efficient host compound for anisole and the methyl-substituted anisoles (MA), clathrating each of these organic solvents with 2:1 host:guest ratios. Furthermore, this host displayed selectivity when presented with mixed guests, and guest–guest competition studies involving the methylanisoles revealed a host selectivity order of p-MA > m-MA > o-MA, whilst the addition of unsubstituted anisole to these experiments showed this guest to now be the preferred one (anisole > p-MA > m-MA > o-MA). Single crystal diffraction analyses indicated the absence of hydrogen bonding between host and guest molecules, and that guests were retained within the host crystal only by means of CH–π, π–π stacking and other short interaction types. The latter involved host aromatic carbon or hydrogen atoms and guest methoxyl or methyl hydrogens and aromatic carbons, as well as host and guest methoxyl hydrogens. Results from thermal analyses provided the reason for the observed selectivity order, with complexes comprising preferred guests anisole and p-MA displaying enhanced thermal stabilities relative to those with o- and m-MA.

Keywords

Host–guest chemistry Supramolecular chemistry DMT Anisole Methylanisole 

Notes

Acknowledgements

Financial support is acknowledged from the Nelson Mandela University and the National Research Foundation (NRF). L. Bolo and K. Ngobo are thanked for thermal analyses.

Supplementary material

10847_2018_858_MOESM1_ESM.pdf (146 kb)
Supplementary material 1 (PDF 145 KB)
10847_2018_858_MOESM2_ESM.pdf (161 kb)
Supplementary material 2 (PDF 161 KB)
10847_2018_858_MOESM3_ESM.pdf (158 kb)
Supplementary material 3 (PDF 158 KB)
10847_2018_858_MOESM4_ESM.pdf (156 kb)
Supplementary material 4 (PDF 156 KB)
10847_2018_858_MOESM5_ESM.txt (3 kb)
Supplementary material 5 (TXT 2 KB)

References

  1. 1.
    Weber, E., Dӧrpinghaus, N., Csӧregh, I.: Versatile and convenient lattice hosts derived from singly bridged triarylmethane frameworks, X-ray crystal structures of three inclusion compounds. J. Chem. Soc. Perkin Trans. 2, 2167 (1990)CrossRefGoogle Scholar
  2. 2.
    Weber, E., Skobridis, K., Wierig, A., Nassimbeni, L.R., Johnson, L.: Complexation with diol host compounds. Part 10. Synthesis and solid state inclusion properties of bis(diarylhydroxymethyl)-substituted benzenes and biphenyls; X-ray crystal structures of two host polymorphs and of a non-functional host analogue. J. Chem. Soc. Perkin Trans. 2, 2123 (1992)CrossRefGoogle Scholar
  3. 3.
    Weber, E., Csӧregh, I., Ahrendt, J., Finge, S., Czugler, M.: Design of roof-shaped clathrate hosts. Inclusion properties and x-ray crystal structures of a free host and of inclusion compounds with 1-butenol and DMF. J. Org. Chem. 53, 5831 (1988)CrossRefGoogle Scholar
  4. 4.
    Weber, E., Dӧrpinghaus, N., Goldberg, I.: Selective clathrate inclusion of primary and secondary amines in a new host series. Crystallographic reasoning of the inclusion behaviour. J. Chem. Soc. Chem. Commun. (1988).  https://doi.org/10.1039/C39880001566 CrossRefGoogle Scholar
  5. 5.
    Toda, F.: Isolation and optical resolution of materials utilizing inclusion crystallization. Top. Curr. Chem. 140, 43 (1987)CrossRefGoogle Scholar
  6. 6.
    Toda, F., Tanaka, K.: Design of a new chiral host compound, trans-4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane. An effective optical resolution of bicyclic enones through host-guest complex formation. Tetrahedron Lett. 29, 551 (1988)CrossRefGoogle Scholar
  7. 7.
    Weber, E., Hecker, M., Csӧregh, I., Czugler, M.: New host family based on small-ring compounds. J. Am. Chem. Soc. 111, 7866 (1989)CrossRefGoogle Scholar
  8. 8.
    Zhang, M., Wang, J., Jin, Z.: Supramolecular hydrogel formation between chitosan and hydroxypropyl β-cyclodextrin via Diels-Alder reaction and its drug delivery. Int. J. Biol. Macromol. 114, 381 (2018)CrossRefGoogle Scholar
  9. 9.
    Shelley, H., Babu, R.J.: Role of cyclodextrins in nanoparticle-based drug delivery systems. J. Pharm. Sci. 107, 1741 (2018)CrossRefGoogle Scholar
  10. 10.
    Huang, D., Wu, D.: Biodegradable dendrimers for drug delivery. Mater. Sci. Eng., C 90, 713 (2018)CrossRefGoogle Scholar
  11. 11.
    Iskierko, Z., Noworyta, K., Sharma, P.S.: Molecular recognition by synthetic receptors: application in field-effect transistor based chemosensing. Biosens. Bioelectron. 109, 50 (2018)CrossRefGoogle Scholar
  12. 12.
    Bereza-Malcolm, L., Aracic, S., Mann, G., Franks, A.E.: The development and analyses of several gram-negative arsenic biosensors using a synthetic biology approach. Sens. Actuators, B 256, 117 (2018)CrossRefGoogle Scholar
  13. 13.
    Seebach, D., Beck, A.K., Heckel, A.: TADDOLs, their derivatives, and TADDOL analogues: versatile chiral auxiliaries. Angew. Chem. Int. Ed. 40, 92 (2001)CrossRefGoogle Scholar
  14. 14.
    Lusi, M., Barbour, L.J.: Solid–vapor sorption of xylenes: prioritized selectivity as a means of separating all three isomers using a single substrate. Angew. Chem. Int. Ed. 51, 3928 (2012)CrossRefGoogle Scholar
  15. 15.
    Barton, B., Hosten, E.C., Pohl, P.L.: Discrimination between o-xylene, m-xylene, p-xylene and ethylbenzene by host compound (R,R)-(–)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol. Tetrahedron 72, 8099 (2016)CrossRefGoogle Scholar
  16. 16.
    Barton, B., Hosten, E.C., Pohl, P.L.: Host (–)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol and guests aniline, N-methylaniline and N,N-dimethylaniline: a selectivity study. Aust. J. Chem. 71, 133 (2018)CrossRefGoogle Scholar
  17. 17.
    Barton, B., Dorfling, S.-L., Hosten, E.C., Pohl, P.L.: Host compounds (+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol (TETROL) and (2R,3R)-(−)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) with guests o-, m- and p- toluidine: a comparative investigation. Tetrahedron 74, 2754 (2018)CrossRefGoogle Scholar
  18. 18.
    Barton, B., de Jager, L., Dorfling, S.-L., Hosten, E.C., McCleland, C.W., Pohl, P.L.: Host behaviour of related compounds, TETROL and DMT, in the presence of two different classes of aromatic guest compounds. Tetrahedron 74, 4754 (2018)CrossRefGoogle Scholar
  19. 19.
    Nassimbeni, L.R., Marivel, S., Su, H., Weber, E.: Inclusion of picolines by a substituted binaphthyl diol host: selectivity and structure. RSC. Adv. 3, 25758 (2013)CrossRefGoogle Scholar
  20. 20.
    Bruker AXS: APEX2, SADABS and SAINT. Bruker AXS, Madison (2010)Google Scholar
  21. 21.
    Sheldrick, G.M.: SHELXT – integrated space-group and crystal-structure determination. Acta Crystallogr. C71, 3 (2015)Google Scholar
  22. 22.
    Hübschle, C.B., Sheldrick, G.M., Dittrich, B.: ShelXle: a Qt graphical user interface for SHELXL. J. Appl. Crystallogr. 44, 1281 (2011)CrossRefGoogle Scholar
  23. 23.
    Barbour, L.J., Caira, M.R., Nassimbeni, L.R.: Enclathration of diethyl ether. J. Chem. Soc. Perkin Trans 2, 1413 (1993)CrossRefGoogle Scholar
  24. 24.
    Caira, M.R., Nassimbeni, L.R., Niven, M.L., Schubert, W.-D., Weber, E., Dӧrpinghaus, N.: Complexation with hydroxy host compounds. Part 1. Structures and thermal analysis of a suberol-derived host and its host–guest complexes with dioxane and acetone. J. Chem. Soc. Perkin Trans 2, 2129 (1990)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  1. 1.Department of ChemistryNelson Mandela UniversityPort ElizabethSouth Africa

Personalised recommendations