The construction route of organic superacids from the combination of organic superhalogens and protons is verified to be a rational one based on a systematic theoretical study covering different planar conjugated backbones, e.g., [C5H5]- and [BC5H6]-, and electron-withdrawing substituents, e.g., -F, -CN and -NO2. In both the gas phase and the solution phase, the acidities of the composites here have a consistent strengthening with the increase of the vertical electron detachment energy of the superhalogen part. Decomposition of the acidity into different contributions further verifies the dominant role of the superhalogen part in the variation of the acidity. Thus, tuning of the acidity of systems of this type could be achieved via rational design of the constituent part of the superhalogen. That is to say, the design of a novel organic superacid with enhanced properties could be guided by the search for a new strong superhalogen of organic nature eventually. Having provided important contributions to the topic of superhalogens, theoretical calculation should be trusted to provide useful guidance for the research of organic superacids and could be expected to promote related experimental studies in the near future.