A new set of four fluorinated aromatic poly(benzamide imide)s was synthesized with the objective of preparing condensation polymers with good processability while maintaining high chemical resistance, thermal stability and good mechanical properties. Their synthesis was carried out using commercially available cycloalkane substituted diamines, 3,5-dinitrbenzoyl chloride and 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) as starting materials. The research was focused on the influence of pendant groups and the testing of a computational methodology that could help to predict polymer properties based on their structure and available QSPR models. To this end, extensive tests were performed on these new poly(imide)s including, IR, NMR, X-ray diffraction, UV absorption, thermal stability, mechanical tests, gas permeation and solubility analyses. The results showed that the materials obtained present properties similar to many available commercial poly(imide)s. On the other hand, computational simulations demonstrated that the strategy followed could be useful in reducing the number of compounds to be synthesized and a the same time, maximize the success ratio of finding polymers with certain desired properties.