Exploring molecular recognition pathways in one- and two-component gels formed by dendritic lysine-based gelators

John G. Hardy*, Andrew R. Hirst, David K. Smith

*Corresponding author for this work

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

This paper provides an integrated overview of the factors which control gelation in a family of dendritic gelators based on lysine building blocks. In particular, we establish that higher generation systems are more effective gelators, amide linkages in the dendron are better than carbamates, and long alkyl chain surface groups and a carboxylic acid at the focal point enhance gelation. The gels are best formed in relatively low polarity solvents with no hydrogen bond donor ability and limited hydrogen bond acceptor capacity. The dendrons with acid groups at the focal point can form two component gels with diaminododecane, and in this case, it is the lower generation dendrons which can avoid steric hindrance and form more effective gels. The stereochemistry of lysine is crucial in self-assembly, with opposite enantiomers disrupting each other's molecular recognition pathways. For the two-component system, stoichiometry is key, if too much diamine is present, dendron-stabilised microcrystals of the diamine begin to form. Interestingly, gelation still occurs in this case, and the systems with amides/alkyl chains are more effective gels, as a consequence of enhanced dendron-dendron intermolecular interactions allowing the microcrystals to form an interconnected network.

Original languageEnglish
Pages (from-to)3399-3406
Number of pages8
JournalSoft Matter
Volume8
Issue number12
Early online date15 Feb 2012
DOIs
Publication statusPublished - 2012

Keywords

  • ACID-TERMINATED POLYDIMETHYLSILOXANES
  • PHASE MATERIALS
  • WEIGHT GELATORS
  • SUPRAMOLECULAR ASSOCIATION
  • PEPTIDIC DENDRIMERS
  • SELF-ORGANIZATION
  • ONE-COMPONENT
  • GELATION
  • ORGANOGELATORS
  • SOLVENT

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry
  • Polymers and Plastics

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