A highly selective OFF-ON red-emitting phosphorescent thiol probe with large stokes shift and long luminescent lifetime

Org Lett. 2010 Jun 18;12(12):2876-9. doi: 10.1021/ol100999j.

Abstract

An OFF-ON red-emitting phosphorescent thiol probe is designed by using the (3)MLCT photophysics of Ru(II) complexes, i.e., with Ru(II) as the electron donor. The probe is non-luminescent because the MLCT is corrupted by electron transfer from Ru(II) to an intramolecular electron sink (2,4-dinitrobenzenesulfonyl). Thiols cleave the electron sink, and the MLCT is re-established. Phosphorescence at 598 nm was enhanced by 90-fold, with a 143 nm (5256 cm(-1)) Stokes shift and a 1.1 mus luminescent lifetime.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Screening Assays, Antitumor
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Humans
  • Luminescence
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Ruthenium / chemistry*
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry

Substances

  • Fluorescent Dyes
  • Organometallic Compounds
  • Sulfhydryl Compounds
  • Ruthenium