Synthesis and Self-Assembly of Shape Amphiphiles Based on POSS-Dendron Conjugates

Molecules. 2017 Apr 21;22(4):622. doi: 10.3390/molecules22040622.

Abstract

Shape has been increasingly recognized as an important factor for self-assembly. In this paper, a series of shape amphiphiles have been built by linking polyhedral oligomeric silsesquioxane (POSS) and a dendron via linkers of different lengths. Three conjugates of octahedral silsesquioxanes (T₈-POSS) and dendron are designed and synthesized and are referred to as isobutyl T₈-POSS gallic acid derivatives (BPOSS-GAD-1, BPOSS-GAD-2, BPOSS-GAD-3). These samples have been fully characterized by ¹H-NMR, 13C-NMR, Fourier transform infrared (FT-IR) spectroscopy and matrix-assisted laser desorption/ionization time of flight (MALDI-TOF) mass spectrometry to establish their chemical identity and purity. Driven by different interactions between POSS and dendron, ordered superstructure can be found upon self-assembly. The stabilities and structures of these samples are further studied by using differential scanning calorimetry (DSC), small-angle X-ray scattering (SAXS), wide-angle X-ray diffraction (WAXD), and molecular simulations. The results show that their melting points range from 74 °C to 143 °C and the molecular packing schemes in the assemblies can form lamellar structure of BPOSS-GAD-3 as determined by the different linkers.

Keywords: dendrimer; hierarchical structure; polyhedral oligomeric silsesquioxane; shape amphiphiles.

MeSH terms

  • Anthracenes / chemistry*
  • Calorimetry, Differential Scanning
  • Dendrimers / chemistry*
  • Magnetic Resonance Spectroscopy
  • Nanoparticles / chemistry
  • Organosilicon Compounds / chemistry*
  • Scattering, Small Angle
  • Spectroscopy, Fourier Transform Infrared
  • Surface-Active Agents / chemical synthesis*
  • Surface-Active Agents / chemistry

Substances

  • Anthracenes
  • Dendrimers
  • Organosilicon Compounds
  • Surface-Active Agents
  • dendron
  • polyhedraloligosilsesquioxane