Molecular two-photon absorption (TPA) has gained great interest over recent years owning to each application in various fields, including spectroscopy, microscopy, 3-D optical data storage, optical power limitation and microfabrication. The requirement for organic molecules with large TPA cross-sections is therefore essential. In the present work the two-photon absorption properties of a series of pyrylium-based chromophores were investigated. The molecules of this series were synthesized by systematically changing the chemical structure of a specific substituent of an initial, strong two-photon absorbing, molecule. Very large TPA cross-sections (1800 GM) and high quantum yields were achieved in the visible red and NIR region of the spectrum. The relation between the chemical structure of the molecules and their TPA performance was discussed. Furthermore, the photobleaching efficiency of these molecules doped in polymer matrices was investigated. Parallel successive patterns were recorded in a polymer matrix via photobleaching. The accuracy of recorded patterns reveals the great potential of these chromophores as memory materials.