Hydrogen supramolecular polymers

J. H. K. K. Hirschbeig, F. H. Beijer, H. A. van Aert, P. C. M. M. Magusin, R. P. Sijbesma, E. W. Meijer, Supramolecular polymers from linear telechelic siloxanes with quadruple hydrogen bonded units , Macromolecules 1999, 32, 2696-2705. 

Ma, Y. Kolomchin, S. V. Zimmerman, S. C. Supramolecular polymer chemistry Self-assembling dendrimers using the DDA AAD (GC-like) hydrogen bonding motif. J. Am. Chem. Soc. 2002,124, 13757-13769. 

Hofmeier H, El-ghayoury A, Schenning APH, Schubert US (2004) New supramolecular polymers containing both terpyiidine metal complexes and quadruple hydrogen bonding units. Chem Commun 318-319... 

The concept of supramolecular polymers containing multiple hydrogen bonding units was introduced over a decade ago by Jean-Marie Lehn (Lehn 1993). In this smdy, three-point hydrogen bonding between bifunctional diamidopyridine and thymine... 

Figure 1.1 (a) Supramolecular polymers developed by Lehn using three-point hydrogen... 

Lange RFM, van Gurp M, Meijer EW. Hydrogen-bonded supramolecular polymer networks. J Polym Sci Part A Polym Chem 1999 37 3657-3670. 

Sivakova S, Bohnsak DA, Mackay ME, Suwanmala P, Rowan SJ. Utilization of a combination of weak hydrogen-bonding interactions and phase segregation to 3field highly thermosensitive supramolecular polymers. J Am Chem Soc 2005 127 18202-18211. 

Figure 5.2 Examples of hydrogen bonding motifs used in supramolecular polymers dimerizing uieidopyrimidone (UPy) functionalized main chain supramolecular polymers (2A), simple one-point complementary hydrogen bonding interactions between pyridine and phenol (2B), and six-point complementary hydrogen bonding interaction between cyanuric acid and the Hamilton wedge receptor (2C).

Armstrong G, Buggy M. Hydrogen-bonded supramolecular polymers a Uterature review. J Mater Sci 2005 40 547-559. 

Park T, Zimmerman SC. Formation of a miscible supramolecular polymer blend through self-assembly mediated by a quadruply hydrogen-bonded heterocomplex. J Am Chem Soc 2006 128 11582-11590. 

Shimizu LS. Perspectives on main-chain hydrogen bonded supramolecular polymers. Polym... 

Brunsveld L, Vekemans JAJM, Hirschberg JHKK, Sijbesma RP, Meijer EW. Hierarchical formation of helical supramolecular polymers via stacking of hydrogen-bonded pairs in water. Proc Natl Acad Sci USA 2002 99 4977-4982. 

Ky Hirschberg JHK, Beijer FH, van Aert HA, Magusin PCMM, Sijbesma RP, Meijer EW. Supramolecular polymers from linear telechelic siloxanes with quadmple-hydrogen-bonded units. Macromolecules 1999 32 2696-2705. 

Fig. 2 The structure of (a) 20 natural L amino acids and (b) aromatic residues that gives rise to (c) aromatic peptide amphiphiles, which form supramolecular polymers through hydrogen bonding and 71-stacking interactions...

Combination of two hydrogen-bonding units in preorganized scaffolds is an effective way to achieve a dimer or a supramolecular polymer (Fig. 3). 

As one example, the observation of hydrogen bonding [7] in natural systems such as peptide helices and DNA base pairs led to a theoretical understanding of this phenomenon. This understanding has permitted the use of hydrogen bonding in synthesis, leading to the preparation of such diverse structures as Rebek s capsules [8], Lehn s supramolecular polymers [9], and Whitesides rosettes [10]. 

In all cases, these aggregates had a uniform diameter of a few nanometers, that is, on the same length scale as the molecular dimensions. Hence, they appeared to be well-defined supramolecular polymers (rather than micellar or vesicular structures) with the propensity to higher-order structure formation. The exact natureofthelatterwasfoundtodependonthenumberofadditionalN—H G=C type hydrogen-bonding sites in the molecules end groups. 

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