A Pd8 Tetrafacial Molecular Barrel as Carrier for Water Insoluble Fluorophore

J Am Chem Soc. 2015 Sep 23;137(37):11916-9. doi: 10.1021/jacs.5b08008. Epub 2015 Sep 10.

Abstract

A new carbazole-based tetraimidazole ligand 1,3,6,8-tetra(1H-imidazol-1-yl)-9-methyl-9H-carbazole (L) has been synthesized. The unsymmetrical nature of L as well as the rotational freedom of imidazole donor moieties around C-N bond make it a special building unit, which upon treatment with cis-(tmeda)Pd(NO3)2 produced an unprecedented single linkage-isomeric Pd8 tetrafacial molecular nanobarrel (PSMBR-1) [tmeda = N,N,N',N'-tetramethylethane-1,2-diamine]. Unlike closed architectures, open barrel architecture of water-soluble PSMBR-1 makes it an ideal host for some water insoluble polyaromatic hydrocarbons in aqueous medium; one such inclusion complex coronene⊂PSMBR-1 was characterized by X-ray diffraction study. Moreover, the potential application of PSMBR-1 as carrier in aqueous medium for the transportation of water insoluble fluorophore (perylene) for live cell imaging is explored.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles / chemistry
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Ligands
  • Models, Molecular
  • Molecular Conformation
  • Nanostructures / chemistry
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Solubility
  • Water / chemistry*

Substances

  • Carbazoles
  • Fluorescent Dyes
  • Ligands
  • Organometallic Compounds
  • Water
  • carbazole
  • Palladium