A series of fluorene-based two-photon absorbing molecules: synthesis, linear and nonlinear characterization, and bioimaging

J Org Chem. 2010 Jun 18;75(12):3975-82. doi: 10.1021/jo1005075.

Abstract

The synthesis, structural, and photophysical characterization of a series of new fluorescent donor-acceptor and acceptor-acceptor molecules, based on the fluorenyl ring system, with two-photon absorbing properties is described. These new compounds exhibited large Stokes shifts, high fluorescence quantum yields, and significantly, high two-photon absorption cross sections, making them well suited for two-photon fluorescence microscopy imaging. Confocal and two-photon fluorescence microscopy imaging of COS-7 and HCT 116 cells incubated with probe I showed endosomal selectivity, demonstrating the potential of this class of fluorescent probes in multiphoton fluorescence microscopy.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Absorption
  • Fluorenes / chemistry*
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • HCT116 Cells
  • Humans
  • Microscopy, Confocal
  • Molecular Imaging*
  • Molecular Structure
  • Photochemistry
  • Photons*

Substances

  • Fluorenes
  • Fluorescent Dyes