A series of new N-arylpyrrole-based chromophores with the donor-pi-donor structure have been designed and synthesized via Wittig-Homer-Emmons olefination and Suzuki coupling reactions. The electronic and optical properties of the designed chromophores could be well tuned by modifying the conjugation bridges and changing the groups linked to the pyrrole moieties through the C-N single bond. All the chromophores exhibited two-photon absorption activity in the range of 730-900 nm with a large two-photon absorption cross section (similar to 1000-1700 GM).