In this contribution, three triphenylamine derivatives were synthesized and their spectral properties were investigated. Knoevenagel condensation of mono-, di-, and tri-aldehydes of triphenylamine with 1,3-indanedione yields D-$pi$-A type dyes with push-pull chromophores. The absorption and luminescence properties of the dyes were discussed in terms of their electronic structures. The results of molecular orbital computer simulations, based on Material Studio, were found to provide a reasonable explanation for the observed spectral properties related to the push-pull features causing dramatic changes in UV-Vis absorption as well as in photoluminescence.