Acetylene-substituted two-photon absorbing molecules with rigid elongated pi-conjugation: synthesis, spectroscopic properties and two-photon fluorescence cell imaging applications

J Fluoresc. 2007 Sep;17(5):573-9. doi: 10.1007/s10895-007-0219-8. Epub 2007 Jun 26.

Abstract

Two asymmetrical molecules with substituted acetylene as central rigid elongated conjugation are reported as potential chromophores for two-photon microscopic imaging. These molecules consist of a typical D-pi-A structure, have different donors (D), the same pi-conjugated center (pi) and the same acceptor (A). Structural characterization and spectroscopic properties, including single-photon (linear) absorption, quantum yields, single-photon fluorescence, and two-photon absorption spectra, were studied in solvents with different polarity. These acetylene-substituted molecules were found to have high two-photon absorption cross-sections (for example, 690 GM for molecule 1 in toluene), which were determined by a two-photon induced fluorescence method using a femtosecond Ti: sapphire laser as excitation source. Single- and two-photon cellular imaging experiments demonstrate that the substituted acetylene derivatives could be one kind of promising two-photon fluorescence probes for cellular imaging.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis
  • Alkynes / chemistry*
  • Cell Line
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Humans
  • Photochemistry
  • Photons
  • Spectrometry, Fluorescence
  • Staining and Labeling

Substances

  • Alkynes
  • Fluorescent Dyes