Design of organic molecules with large two-photon absorption cross sections

Science. 1998 Sep 11;281(5383):1653-6. doi: 10.1126/science.281.5383.1653.


A strategy for the design of molecules with large two-photon absorption cross sections, delta, was developed, on the basis of the concept that symmetric charge transfer, from the ends of a conjugated system to the middle, or vice versa, upon excitation is correlated to enhanced values of delta. Synthesized bis(styryl)benzene derivatives with donor-pi-donor, donor-acceptor-donor, and acceptor-donor-acceptor structural motifs exhibit exceptionally large values of delta, up to about 400 times that of trans-stilbene. Quantum chemical calculations performed on these molecules indicate that substantial symmetric charge redistribution occurs upon excitation and provide delta values in good agreement with experimental values. The combination of large delta and high fluorescence quantum yield or triplet yield exhibited by molecules developed here offers potential for unprecedented brightness in two-photon fluorescent imaging or enhanced photosensitivity in two-photon sensitization, respectively.

Publication types

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

MeSH terms

  • Aniline Compounds / chemistry*
  • Chemical Phenomena
  • Chemistry, Physical
  • Fluorescence*
  • Photochemistry
  • Photons*
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry*


  • 4,4'-bis(di-n-butylamino)stilbene
  • Aniline Compounds
  • Stilbenes