Silicon Substitution in Oxazine Dyes Yields Near-Infrared Azasiline Fluorophores That Absorb and Emit beyond 700 nm

Org Lett. 2018 Aug 3;20(15):4482-4485. doi: 10.1021/acs.orglett.8b01786. Epub 2018 Jul 17.

Abstract

Exchanging the bridging oxygen atom in rhodamine dyes with a dimethylsilyl group red-shifts their excitation and emission spectra, transforming orange fluorescent rhodamines into far-red Si-rhodamines. To study the effect of this substitution in other dye scaffolds, synthetic approaches to incorporate silicon into the bridging position of oxazine dyes were developed. The fluorescence of the compact azasiline dyes ASiFluor710 and ASiFluor730 is red-shifted by 57-83 nm from that of Oxazine 1.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Fluorescent Dyes / chemical synthesis*
  • Molecular Structure
  • Organosilicon Compounds / chemical synthesis*
  • Oxazines / chemistry*
  • Oxidation-Reduction
  • Oxygen / chemistry
  • Rhodamines / chemistry
  • Silicon / chemistry*
  • Spectrometry, Fluorescence
  • Structure-Activity Relationship

Substances

  • Fluorescent Dyes
  • Organosilicon Compounds
  • Oxazines
  • Rhodamines
  • Oxygen
  • Silicon