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Inclusion of tetramethylpyrazine in channels of the organic zeolite 2,4,6-tris(4-bromophenoxy)-1,3,5-triazine

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Abstract

2,4,6-tris(4-bromophenoxy)-1,3,5-triazine (BrPOT) features a channel size (11–12 Å) allowing the inclusion of large guest molecules such as tetramethylpyrazine (TMPZ). TMPZ forms π-stacks (d: 3.5 Å) along channels of BrPOT and shows rotational disorder for methyl positions. Co-inclusions of I2 resulted in a doped state where I2 molecules are oriented perpendicular to the channel axis with positional disorder as well. The particular orientation of I2 molecules is evident from the observed dichroism.

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References

  1. Saha, B.K., Jetti, R.K.R., Reddy, L.S., Aitipamula, S.: Halogen trimer-mediated hexagonal host framework of 2,4,6-tris(4-halophenoxy)-1,3,5-triazine: Supramolecular isomerism from hexagonal channel (X = Cl, Br) to cage structure (X = I), Cryst. Growth Design. 5, 887–899 (2005); Saha, B.K., Aitipamula, S., Banerjee, R., Nangia, A., Jetti, R.K.R., Boese, R., Lam, C.-K., Mak, T.C.W.: Hexagonal host framework of syn-aryloxytriazines stabilized by weak intermolecular interactions. Mol. Cryst. Liq. Cryst. 440, 295–316 (2005); Jetti, R.K.R., Xue, F., Mak, T.C.W., Nangia, A.: 2,4,6-tris-4-(bromophenoxy)-1,3,5-triazine: a hexagonal host framework assembled with robust Br...Br trimer synthons. Cryst. Eng. 2, 215–224 (1999); Reichenbächer, K., Süss, H.I., Stoeckli-Evans, H., Bracco, S., Sozzani, P., Weber, E., Hulliger, J.: Modification of channel structures by fluorination, New J. Chem. 28, 393–397 (2004)

    Google Scholar 

  2. Allrock, H.R., Siegel, L.A.: Phosphonitrilic compounds. III. 1 Molecular inclusion compounds of tris(o-phenylenedioxy)phosphonitrile trimer. J. Am. Chem. Soc. 86, 5140–5144 (1964); Hertzsch, T., Kluge, S., Weber, E., Budde, F., Hulliger, J.: Surface recognition of dipolar molecules entering channels of the organic zeolite tris(o-phenylenedioxy)cyclotriphosphazene, Adv. Mater. 13, 1864–1867 (2001)

    Google Scholar 

  3. Suess, H.I., Lutz, M., Hulliger, J.: Inclusion of fullerenes into channels of 2,4,6-tris-4-(bromophenoxy)-1,3,5-triazine (BrPOT), Cryst. Eng. Comm. 4, 610–612 (2002); Reichenbächer, K., Neels, A., Stoeckli-Evans, H., Balasubramaniyan, P., Müller, K., Matsuo, Y., Nakamura, E., Weber, E., Hulliger J.: New fluorinated channel-type host compounds, Cryst. Growth Design. 7, 1399–1405 (2007); Bonin, M., Lüthi, T.A., Reichenbächer, K., Bürgi, H.-B., Hulliger, J.: Inclusion of C60 into cages of 2,4,6-tris(4-iodophenoxy)-1,3,5-triazine and classification of known triazine related inclusion structures, to be submitted

    Google Scholar 

  4. Stoe & Cie.: IPDS Software, Stoe & Cie GmbH, Darmstadt, Germany, (2005)

  5. Sheldrick, G.: Phase annealing in SHELX-90: direct methods for larger structures. Acta. Cryst. A46, 467–473 (1990)

    CAS  Google Scholar 

  6. Sheldrick, G.: SHELXL-97, Program for crystal structure refinement, University of Göttingen, Germany (1997)

    Google Scholar 

  7. Mac Rae, C.F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., van de Streek, J.: Visualization and analysis of crystal structures. J. Appl. Cryst. 39, 453–457 (2006)

    Article  CAS  Google Scholar 

  8. Bailey, R.D., Buchanan, M.L., Pennington, W.T.: Molecular complexes of 1,4-diazines with iodine. Acta Cryst. C48, 2259–2262 (1992)

    CAS  Google Scholar 

  9. Couderc, G., Bonin, M., Neels, A., Hauser, J., Sozzani, P., Hulliger, J.: Iodine-pyrazine chain inside the channel of tris(o-phenylenedioxy)cyclotriphosphazene, to be submitted

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Acknowledgments

This work was supported by the Swiss National Foundation, project Nr. 200021-113358/1. We thank Prof. U. Krähenbühl for ICP-MS measurements.

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Correspondence to Jürg Hulliger.

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Couderc, G., Bonin, M., Labat, G. et al. Inclusion of tetramethylpyrazine in channels of the organic zeolite 2,4,6-tris(4-bromophenoxy)-1,3,5-triazine. J Incl Phenom Macrocycl Chem 61, 377–379 (2008). https://doi.org/10.1007/s10847-008-9433-5

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  • DOI: https://doi.org/10.1007/s10847-008-9433-5

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