Synthesis and Intramolecular Energy- and Electron-Transfer of 3D-Conformeric Tris(fluorenyl-[60]fullerenylfluorene) Derivatives

Molecules. 2019 Sep 13;24(18):3337. doi: 10.3390/molecules24183337.

Abstract

New 3D conformers were synthesized to show a nanomolecular configuration with geometrically branched 2-diphenylaminofluorene (DPAF-C2M) chromophores using a symmetrical 1,3,5-triaminobenzene ring as the center core for the connection of three fused DPAF-C2M moieties. The design led to a class of cis-cup-tris[(DPAF-C2M)-C60(>DPAF-C9)] 3D conformers with three bisadduct-analogous <C60> cages per nanomolecule facing at the same side of the geometrical molecular cis-cup-shape structure. A sequential synthetic route was described to afford this 3D configurated conformer in a high yield with various spectroscopic characterizations. In principle, a nanostructure with a non-coplanar 3D configuration in design should minimize the direct contact or π-stacking of fluorene rings with each other during molecular packing to the formation of fullerosome array. It may also prevent the self-quenching effect of its photoexcited states in solids. Photophysical properties of this cis-cup-conformer were also investigated.

Keywords: 3D-configurated nanostructures; Tri[60]fullerenyl stereoisomers; cis-cup-form of 3D-stereoisomers; intramolecular electron transfer for superoxide radical production; intramolecular energy transfer for singlet oxygen production; tris(diphenylaminofluorene).

MeSH terms

  • Electron Transport
  • Fluorenes / chemical synthesis*
  • Fluorenes / chemistry
  • Fullerenes / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism

Substances

  • Fluorenes
  • Fullerenes