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A direct comparison of one- and two-component dendritic self-assembled materials: elucidating molecular recognition pathways

Huang, B.Q., Hirst, A.R., Smith, D.K., Castelletto, V. and Hamley, I.W. (2005) A direct comparison of one- and two-component dendritic self-assembled materials: elucidating molecular recognition pathways. Journal of the American Chemical Society, 127 (19). pp. 7130-7139. ISSN 0002-7863

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To link to this article DOI: 10.1021/ja050412d

Abstract/Summary

This paper compares and contrasts, for the first time, one- and two-component gelation systems that are direct structural analogues and draws conclusions about the molecular recognition pathways that underpin fibrillar self-assembly. The new one-component systems comprise L-lysine-based dendritic headgroups covalently connected to an aliphatic diamine spacer chain via an amide bond, One-component gelators with different generations of headgroup (from first to third generation) and different length spacer chains are reported. The self-assembly of these dendrimers in toluene was elucidated using thermal measurements, circular dichroism (CD) and NMR spectroscopies, scanning electron microscopy (SEM), and small-angle X-ray scattering (SAXS). The observations are compared with previous results for the analogous two-component gelation system in which the dendritic headgroups are bound to the aliphatic spacer chain noncovalently via acid-amine interactions. The one-component system is inherently a more effective gelator, partly as a consequence of the additional covalent amide groups that provide a new hydrogen bonding molecular recognition pathway, whereas the two-component analogue relies solely on intermolecular hydrogen bond interactions between the chiral dendritic headgroups. Furthermore, because these amide groups are important in the assembly process for the one-component system, the chiral information preset in the dendritic headgroups is not always transcribed into the nanoscale assembly, whereas for the two-component system, fiber formation is always accompanied by chiral ordering because the molecular recognition pathway is completely dependent on hydrogen bond interactions between well-organized chiral dendritic headgroups.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11343
Uncontrolled Keywords:2-DIRECTIONAL CASCADE MOLECULES, GEL-PHASE MATERIALS, ORGANIC-SOLVENTS, L-LYSINE, ASSOCIATION PROPERTIES, PEPTIDIC DENDRIMERS, GELATION PROPERTIES, ROOM-TEMPERATURE, AQUEOUS-SOLUTION, LATENT GELATORS
Publisher:American Chemical Society

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