Polymorphism of amino acid-based dendrons: from organogels to microcrystals

Chem Asian J. 2011 May 2;6(5):1163-70. doi: 10.1002/asia.201000529. Epub 2011 Feb 24.

Abstract

There is a delicate balance for a low-weight molecule to behave as a gelator or crystal. The synthesis of two novel amino acid-based naphthalene-dendrons, Nap-G1 and Nap-G2 is described. Both dendrons display polymorphic properties in organic solvents. Nap-G1 developed a fibrous network with β-sheet architecture in cyclohexane but exhibited a spherulitic network in mixed solvents (chloroform/petroleum ether 1:5, v/v). On the other hand, Nap-G2 acted as an efficient organogelator in chloroform but formed crystalline fibers in relatively high polarity solvents (such as acetone and methanol). Combinations of characterizations have been employed to study the polymorphism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Chloroform / chemistry
  • Circular Dichroism
  • Crystallization
  • Cyclohexanes / chemistry
  • Dendrimers / chemistry*
  • Dipeptides / chemical synthesis
  • Dipeptides / chemistry*
  • Gels / chemistry*
  • Magnetic Resonance Spectroscopy
  • Naphthalenes / chemical synthesis
  • Naphthalenes / chemistry*
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Amino Acids
  • Cyclohexanes
  • Dendrimers
  • Dipeptides
  • Gels
  • Naphthalenes
  • Oligopeptides
  • Cyclohexane
  • Chloroform