Abstract
This review describes the synthesis and characterization of two different types of supramolecular assemblies. As non-covalent interactions hydrogen bonding and coordination chemistry have been used. Various techniques were studied, like NMR spectroscopy, X-Ray crystallography, ESMS and MALDI TOF mass spectrometry, and AFM to characterize these assemblies both in the solid state and in solution. Assembly of the calix[4]arene boxes via hydrogen bonding gives particles that are 3–5 nm in size, whereas self-assembly of the metallo-pincer ligands leads to spherical assemblies with diameters in the range of 100 to 400 nm, with standard deviations in the order of 10–15 %. The controlled assembly approach allows a precise control of size and assemblies with molecular weights up to 10,000 Dalton have been realized. The combination of hydrogen bonding and metal-coordination has been achieved in the synthesis of metallodendrimers with a hydrogen-bonded core.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Timmerman, P., Verboom, W., Van Veggel, F.C.J.M., Van Hoorn, W.P., and Reinhoudt, D.N. An organic molecule with a rigid cavity of nanosize dimensions, Angew. Chem. Int. Ed. Engl. 33, 1292–1295
Higler, I., Timmerman, P., Verboom, W., and Reinhoudt, D.N. (1996) Combination of calix[4]arenes and resorcinarenes for the complexation of steroids, J. Org. Chem. 61, 5920–5931
Timmerman, P., Verboom, W., Van Veggel, F.C.J.M., Van Duynhoven, J.P.M., and Reinhoudt, D.N. (1994) A novel type of stereoisomerism in calix[4]arene-based carceplexes, Angew. Chem. Int. Ed. Engl 33, 2345–2348
Van Dienst, E., Snellink, B.H.M., Von Pieckartz, I., Engbersen, J.F.J., and Reinhoudt, D.N. (1995) Novel water-soluble cyclodextrin-calix[4]arene host molecules with strongly enhanced binding properties, J. Chem Soc., Chem. Commun. 1151–1152
Rudkevich, D.M., Verboom, W., and Reinhoudt, D.N. (1995) Capped biscalix[4]arene-Zn-porphyrin: metalloreceptor with a rigid cavity, J. Org. Chem. 60, 6585–6587.
Whitesides, G.M., Simanek, E.E., Mathias, J.P., Seto, C.T., Chin, D.N., Mammen, M., and Gordon, D.M. (1995) Noncovalent synthesis: using physical-organic chemistry to make aggregates, Acc. Chem. Res. 28, 37–44 and references cited therein.
Vreekamp, R. H., Hubert, M., Van Duynhoven, J.P.M., Verboom, W., and Reinhoudt, D. N. (1996) Molecular Boxes based on calix[4]arene double rosettes, Angew. Chem., Int. Ed. Engl. 35, 1215–1218.
Timmerman, P., Vreekamp, R. H., Hulst, R., Verboom, W., Reinhoudt, D. N., Rissanen, K., Udachin, K. A., and Ripmeester J. (1997) Noncovalent assembly of functional groups on Calix[4]arene Molecular Boxes, Chem. Eur. J. 3, 1823–1832.
Jolliffe, K.A., Crego Calama, M., Fokkens, R., Nibbering, N.M.M., Timmerman, P., and Reinhoudt, D. N. Characterization of hydrogen bonded supramolecular assemblies by Ag+ assisted MALDI TOF mass spectrometry, submitted for publication.
Huck, W.T.S., Van Veggel, F.C.J.M., Kropman, B.L., Blank, D.H.A., Keim, E.G., Smithers, M.M.A., and Reinhoudt, D.N. (1995) Large self-assembled organopalladium spheres, J. Am. Chem Soc. 117, 8293–8294
Huck, W.T.S., Van Veggel, F.C.J.M., and Reinhoudt, D.N. (1997) Self-assembly of hyperbranched spheres, J. Mater. Res. 7, 1213–1219.
Huck, W.T.S., Snellink-Ruël, B.H.M., Lichtenbelt, J.W.Th., Van Veggel, F.C.J.M., and Reinhoudt, D.N. (1997) Self-assembly of hyperbranched spheres, Chem Commun. 9–10.
Huck, W.T.S., Snellink-Ruël, B.H.M., Van Veggel, F.C.J.M., and Reinhoudt, D.N. (1997) New building blocks for the noncovalent assembly of homo- and hetero-multinuclear metallodendrimers, Organometallics, 16, 4287–4291.
Huck, W.T.S., Van Veggel, F.C.J.M., and Reinhoudt, D.N. (1996) Controlled assembly of nanosized metallodendrimers, Angew. Chem., Int. Ed. Engl. 35, 1213–1215.
Huck, W.T.S., Van Veggel, F.C.J.M., Sheiko, S., Möller, M., and Reinhoudt D.N. Molecular thin films of metallodendrimers, submitted.
Huck, W.T.S., Rohrer, A., Anilkumar, A.T., Fokkens, R., Nibbering, N.M.M., Van Veggel, F.C.J.M., and Reinhoudt, D.N. Noncovalent synthesis of multi-porphyrin systems, New J. Chem, accepted.
Huck, W.T.S., Hulst, R., Timmerman, P., Van Veggel, F.C.J.M., and Reinhoudt, D.N. (1997) Noncovalent synthesis of nanostructures: combining coordination chemistry and hydrogen bonding, Angew. Chem., Int. Ed. Engl. 36, 1006–1008.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Reinhoudt, D.N., Timmerman, P., Van Veggel, F.C.J.M. (1999). Non-Covalent Synthesis and Characterization of Large Supramolecular Assemblies. In: Tsoucaris, G. (eds) Current Challenges on Large Supramolecular Assemblies. NATO Science Series, vol 519. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-5284-6_5
Download citation
DOI: https://doi.org/10.1007/978-94-011-5284-6_5
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-6224-4
Online ISBN: 978-94-011-5284-6
eBook Packages: Springer Book Archive