Synthesis and Linear and Nonlinear Optical Properties of Three Push-Pull Oxazol-5(4H)-one Compounds.

Three uncharged push-pull oxazol-5(4H)-ones were synthesized and thoroughly characterized. The examined molecules contained electron-donor and electron-acceptor groups interacting via a π-conjugated bridge. Spectral properties of the oxazol-5(4H)-ones were studied in detail in three solvents of different polarities. The results indicate a solvatochromic shift toward lower energy for the charge-transfer state. The compounds are weakly fluorescent in polar solvents, but they have high fluorescence quantum yields in nonpolar solvents. Their two-photon absorption (2PA) properties were characterized by the open- and closed-aperture Z-scan technique, by the pump-probe technique, and by the two-photon excited fluorescence method. The dyes exhibit relatively high effective two-photon absorption cross sections ranging from 490 to 2600 GM at ~100 GW/cm(2), according to the Z-scan results, which are found, however, to contain significant contribution from higher-order absorption processes. In addition, these compounds display good photostability.